The Art of the Update

Nine out of ten companies fail to regularly publish product updates for their customers. 

For those that do, most aren’t that good. 

It's a shame because properly executed updates can remind current customers of the value they receive, entice new customers to join, and, should you increase your prices, help customers understand what they are paying more for.

You’re leaving money on the table by not publishing frequent, benefits-focused product updates. 

This extensively researched piece will:

1. Help you understand the value of writing great customer updates.
2. Provide extensively researched examples of customer updates.
3. Break down best practices derived from our research into rules you can follow, and
4. Offer you some easy-to-use templates.

Remember, you’re already improving your product; you deserve credit for that hard work.

Let’s dive in.

Why don’t we send customer updates?

I’ve spent many years consulting with product teams in one way or another. Despite having been convinced of the value of product updates for some time, I’ve been somewhat surprised by how few teams decide to write frequent product updates.

When I ask directly I’ve gotten several reasons why teams don’t publish product updates more frequently, including:

1. “We don’t have an existing process to write and format the update.”
2. “We’re already so busy building the product, we don’t have time to publish updates.”
3. “We don’t have a team or person who’s accountable for publishing updates.”

These are all pretty reasonable, and generally delivered with a straight face from a sane person. 

I have two parallel theories here. 

The first theory is that if you’re not in the habit of doing anything, the activation energy required to start is high. 

Companies of every size, from startups to the largest companies in the world, feel overworked. So the notion of spending 10 hours building and 10 hours writing updates is rejected in favor of 20 hours of building.

Moreover, it can be surprisingly complex to figure out who “owns” this process. The developers are most familiar with the changes, but are also stereotypically the worst at communicating with customers. The marketing team is great at talking to customers, but might not have the full story on the changes that are happening. 

There’s definitely a team effort involved which gets way easier once the process is in motion.

The second theory is that most teams dramatically underestimate the value of what great customer updates can do for them. 

Let’s talk about that.

Why should we send customer updates?

Just like a customer reading your product update, you want to know: “What’s it in for me? How does following this make my business better?”

Awesome customer updates benefit your business by:

• Preventing churn
• Increasing new customers
• Boosting expansion revenue
• Setting up for a price increase
• Building trust
• Earning referrals and testimonials

Preventing churn

Great customer updates prevent churn in two key ways.

First, it’s easy to toil away on the product without updating your customers. You might reason that if you’re going to spend 10 hours improving the product, and 10 hours writing an update, it’d be better spending 20 hours improving the product.

Wrong!

(Actually, doubly so, as writing customer updates should be fast. We’ll cover that later.)

You need to get credit for your code. Without updates, customers cannot see your hard effort, and most products appear to stagnate. Getting frequent customer updates does triple duty: it shows that your team is hard at work, it shows that you’re always delivering more customer value, and it shows that your team is thoughtful and customer-focused.

Consider this from your customer’s perspective.

Say you’re a business that has two software subscriptions billed monthly, both are right on the edge of how much you’d like to pay a la Van Westendorp’s Price Sensitivity Meter where “the price is starting to get expensive, but you would still purchase the product.”

One company sends weekly updates with new features, changes, and ways that people are using their product to make more money.

The second company sends nothing.

Which product is more likely to get cut when the budget tightens?

I’ve heard this line directly from customers: every monthly invoice is a decision on whether they should churn. Most subscription products auto-renew. Don’t mistake that to mean staying is the presumptive choice for every customer. 

You’ll be right until the moment you’re wrong, and then they’re gone.

You must strive to win your customers' business with every invoice and never take them for granted. Frequent customer updates are our way of  showing customers that they are important to us.

Also, It turns out that small, frequent updates appeal to investors too!

Increasing new customers

Many businesses mistakenly think that only existing customers are interested in product updates. 

This misconception is self-reinforcing since many businesses hide product updates behind a login screen, and new customers never see them.

The reality is that many potential customers will review the past customer updates to gauge whether the product is stagnating or improving.

After an extended sales process, a large customer I was courting chose a competitor. Since I had formed a strong working relationship with this company, they were willing to share their “considerations spreadsheet” with me. The spreadsheet captured all of the reasons they went with our competitor. 

This was eye-opening on a few fronts. Notably, one item stood out: the number of product updates last quarter. Ours was at zero – not because we hadn’t made any updates, but because they couldn’t find them on our blog. 

It felt awful reading this because we had published updates to our customers over this timeline, but there wasn’t any way for their team to find them.  We were marked with a big “X” – not even a zero, but an “X”.”

However, there are two silver linings.

First, since prospective customers aren't using the product and may not understand the significance of each update, their evaluation is binary. “Does the company we’re considering have frequent updates, yes or no?”

This means that you can get into the “yes” column by simply showing up.

Second, once you establish a reputation for frequent updates, this becomes a potent selling point. Ensure that anyone speaking to leads or trials emphasizes your commitment to frequent updates; it will differentiate you!

Though it’s not really my style, if you’re aware of a competitor consistently failing to update their customers, you could use this to your advantage.

You always hear stories like “worse product but better marketing, so they won the market.” 

Frequent customer updates are a big part of that marketing advantage.

Boosting expansion revenue

“As the complexity of a product increases, the proportion of customers familiar with all of its features decreases.” - Sierakowski’s Law.

Put another way, the more effort you put into your product, the harder you must work to educate customers about it. 

If you really want your eyes opened on this I’d recommend conducting synchronous cancellation calls (as opposed to self serve/email cancellation). Simply ask, “Why are you leaving?” and/or “Is there anything we could have done to keep you?”

The number of customers who could have been retained had they known about a specific feature – one that you indeed offer – is maddening.

This happened to me all the time at Baremetrics:

Me: “I’m so sorry we couldn’t meet your needs. To help us improve our product for future customers, is there anything we could have done to keep your business?”

Ex-Customer: “Yeah, no worries, we’ve found a product that works better for us. We would have loved to have stayed but we needed a product that supported custom dashboards.”

Me: “Oh, wild. We actually do offer custom dashboards!”

Ex-Customer: “Oh, weird! Haha. We would have stayed if we would have known that.”

Me: “Yeah, that’s wild you left because you thought we didn’t have that.”

Ex-Customer: “Yeah, hahaha, wild.”

Me: “...”

Ex-Customer: “......”

Me: “Well, thanks for your time!”

This dialogue highlights a significant oversight: the assumption that customers are aware of the entire product. If a customer isn’t using a specific feature we assume they know about it, but just don’t want it.

This is particularly true for add-on features, or those that are exclusive to higher-tier plans. With add-ons “out of sight, out of mind” it’s very likely that your customers are simply unaware these features exist.

Frequent customer updates can bring these features to light. Below, in the research section, we explore various techniques to maximize expansion revenue through customer updates, including:

1. Finding new ways to talk about add-on features, repeatedly.
2. Clearly stating feature availability, for example, “available to business plan customers and above” or “for users of our commerce hub add-on.”
3. Providing space for persistent reminders, such as, keeping an add-on feature on the "what's new" page for several months after launch.

In short, great customer updates tell your customer when add-on features are available, remind them they exist, and keep those items top of mind when they’re ready to upgrade.

Setting up for a price increase

Price increases are an often inevitable aspect of running a business.

Managing a company is challenging, and the likelihood that you nailed your pricing in those early tumultuous days is slim.

Even if you were successful in picking the right price, external factors like inflation and internal factors such as expanding expenses are likely to require adjustments.

While your expenses in year one were a $5 Heroku dyno and a $7.99/year domain, you might find yourself in year five with a 20-person team, a $160k per month salary expense, an $80k per month cloud bill, and a $7.99 domain.

When all other options are exhausted and you realize a price increase is necessary, best practices dictate transparent communication with customers. This involves outlining the forthcoming changes with your customers, emphasizing the improvements made over the past five years in order to justify the increase.

14 seconds after this email goes out you will get a spike of traffic as customers beeline towards whatever list of product updates you have available to decide for themselves. Woe be upon anyone who decided not to frequently update this list.

If customers visit the update log and see that there’s only seven updates spread across the past three years–you’re in trouble.

I’ve been there. I know the feeling of being so overwhelmed by a massive feature and bug backlog that you devote 100% of the team’s time to tackling it. Know that if you do this you’re opening yourself for a gigantic pain when its price increase season.

Now let’s totally change perspective. 

Imagine yourself as the customer who’s receiving the price increase update email in this scenario. 

You get the price increase email. It is well-crafted and includes justifications, but you want to see these justifications with your own eyes. You go to the customer update log and scroll back to three years ago, the date when you became a customer. 

You see how many posts are ahead of you, they’ve done one a week for the past three years, 156 updates since you started paying for the product.

You can be annoyed, and you can also determine that the price is just too much for the value you get, but no one can start to make the argument that that company hasn’t been extremely busy, wholly focused on making the product better for their customers.

This is the experience we’re looking to create for our customers should we ever need to increase our prices.

Building Trust

Trust is a simple but powerful outcome of frequent updates. 

People are wary of strangers, but tend to trust those they hear from frequently. In entertainment, for example, viewers of Twitch streamers often begin to think they’re friends with them. 

My advice is to strive for regular communication without getting your customers to fall in love with you. If you can avoid it. 

Building trust opens the door to two-way communication, a vital asset. If you’ve ever tried to speak to a customer who hasn’t been contacted in a long time, it can be challenging to get anything back from them at all. 

It’s a bit shocking when you experience this first hand. Once, after a prolonged silence, I sent a simple three question survey to over 100k active customers, and only received 14 responses. 

When I ran TeamPassword, I sent out similar surveys. Our list was much smaller, but because I was actively in touch with most customers our surveys would get opened by 30% of recipients, completed by 90% of the people who started them, and 50% of the respondents responded “yes” to “may we follow up with you for more information?”

When customers hear from you frequently, they’re less likely to think there’s a hidden agenda. They might even reach out to you first, or at least  be more receptive when you ask for product feedback, check in with an account review, or casually inquire if a new add-on might be something they’d find useful.

Earning referrals and testimonials

Sending frequent updates starts a conversation. Each customer interaction is a lottery ticket, and the jackpot is them responding: “This is great!”

Companies invest significant time and money in obtaining testimonials, reviews, and referrals because these elements are highly valuable, making the effort worthwhile. 

Having a customer respond to an update positively is the difference between inbound and outbound sales. Occasionally, a customer’s note is comprehensive enough to screenshot it and feature it on your marketing site (with their permission). 

At other times you might be able to get to that full testimonial with a few follow-up questions. 

This process is much easier than collecting customer quotes through an outbound approach. 

With positive sentiment coming in from your customers, referrals and reviews are just an ask away. Great reviews and referrals exist in a funnel; only a small percentage of customers will write a positive note, and only a fraction of those wlll follow through with a testimonial.

That’s OK; maintaining open communication is valuable itself. However, I’ve never seen this level of interaction fail to result in referrals and testimonials, so hopefully, that motivates you to keep the updates coming.

The Research: Examples in the wild

I scoured the internet through both space and time to find both the best and worst practices, from the fortune 500 to indie hackers. Below is a summary of my research notes so you can see (and draw your own conclusion) about the best customer update practices and tactics.

Researched Companies:

• Slack
• Trello
• Github
• Basecamp
• Mailchimp
• HubSpot
• Baremetrics

Slack

Slack is perhaps THE customer update OG. I decided to jump into the wayback machine to see how they got on the path of solid customer updates.

Here’s a fairly typical update from March 2018:

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There’s a lot to like here.

The updates are clear and concise, with a lot of links for people who want to read more (hint: basically no one wants to read more.) Being concise is generally preferred by customers, and it's less work for us to do! Win win.

As a matter of style the language matches their brand, ala “Quicker switcheroos,” making the updates feel relevant. This doesn’t mean that your updates should be cheeky, in fact it’s a bit cringe when a serious brand tries to be fun, but it is a best practice observed in the best updates to make sure the language you use in the updates matches your brand.

Serious updates are fine for serious companies, I don’t want an update from my doctor that my “panky is all inflamoed.”

Slack is not afraid to promote boring updates which is a rare but powerful strength. One of the reasons why Slack has pages of updates every month is that they’re not afraid to take credit for their work.

“Admin can delete private channels” actually sounds like it could have been a bug (or at least an oversight,) but that’s no reason not to share the update. The people who are impacted by this change will be thrilled to read the update, the people who don’t care will skim past.

The outcomes for promoting boring updates are either excitement that you made the product better for them or basic appreciation that you’re generally making the product better. The only way to lose is to say nothing (which is what most teams do.)

Slack is also not afraid to share bad news in updates, consider this note from the may 2018 update:

If you don’t remember this was a big deal at the time, and people were pretty upset! Slack had the option to put this update outside of the normal stream, or, not say anything at all. But including this bad news allowed them to get ahead of the conversation by explaining their reasoning, and heading off the biggest area of real concern: accessibility.

As a running theme, turning things off and removing features is also work, so if you truly have the conviction that this is best for your customer or your business, take credit for that work too. Removing IRC gateways from Slack infuriated many nerds at the time, but I’m willing to bet exactly zero people remember this, and they seem to have done pretty well subsequently.

Slack also excels by having a persistent location to keep track of wins on a schedule. When you visit their releases page (https://slack.com/releases) they show the latest product updates chronologically, but support their biggest customer benefits directly below:

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Because our goal is to have frequent updates we can’t be sure that our most recent updates cover all of the major benefits we provide to customers. Having a hard-coded benefits section in the same place where a potential customer might review product updates ensures that you have your bases covered, it’s the multi-vitamin of benefits focused language.

While I think basically everyone could do a better job at connecting the dots from feature releases to customer benefit, having a relatively static section like the one above makes sure you always have a foundation to work off of.

Trello

Instead of focusing on individual releases Trello tends to keep their schedule by rolling up posts which feature new improvements alongside old improvements. While this can make it difficult to see what’s new at a glance, it has the intended effect of seeing a large number of what seem like very large features every time you visit the product page on their blog.

Trello shows off a powerful technique, featuring popular posts, at the top of their product page:

They still have posts sorted by most recent below, however having popular posts up top make sure that everyone visiting this page is always hit by the “best of.” This is particularly powerful for prospects, Trello puts their best foot forward in public for any potential customers considering the product.

Let’s do a deeper dive on the “Advanced Checklists” roll up post.

It’s clear Trello’s goal is to be comprehensive. Because they’re bringing up different checklist use cases and all the associated features they provide a very three dimensional view on what it’s like using checklists in Trello. This also has the added benefit of making the post customer focused since it only exists to help their customers make their way around this feature set, supported by customer quotes.

I also love their strategy of adding clarity by focusing on a specific user type. I barely use checklists in Trello, I’d skip this post. Knowing that only the diehard checklist users will be reading the post allows them to go deep into the topic, spending more time going deep into the specifics:

If your goal is to get every update out to every customer you have to appreciate that most users are not going to geek out over a niche feature like checklist task automations. Focusing on a specific user type lets you go deep, presenting each nuance in full detail.

A hugely winning strategy from this section is including customer quotes. Having a quote from a customer means two things. First, the feature being described actually solved a real problem in the world. Second, it proves that someone cares enough to write a quote.

The more you can defer to customer quotes the better, they’re the ones that matter. And it might even be less work for you if they proactively write the quote… but more often than not you’ll need to craft or edit the quote as they did (spy the usage of …’s in their quotes.)

I have no evidence, but I suspect that this quote was either cherry picked or co-created given the inclusion of the last line “X feature has been the biggest upgrade to Trello for me in a long time.”

I’d guess that one of the major reasons for churn and general customer satisfaction is that “Trello hasn’t been upgraded in forever.” This quote arms the team with a bit of backup against that point. </conjecture>

Lightning round:

• They build clarity via a modified bottom line up front, they’re super clear on what makes them “advanced checklists” at the beginning of the article.
• Great “you” language. For example “view all of your work in one place” and “Get more done by changing your POV.”
• They feature both being precise and highlight specific benefits by specifying who gets access to what feature. Trello has a large number of different plans, they include inline which plan gets which feature.
• They dip into being multimedia and increase clarity by providing plentiful product pictures which pervade the post.

Trello’s approach is great to wow current and potential customers who visit the product updates page. Everything is so well crafted and deliberate.

That obviously comes at the cost of needing to spend a good amount of time and effort writing these posts.

There’s also the question of style, this post begins with a quote from the book “The Checklist Manifesto.” I personally don’t think that’s words well spent, serving as a counter example of being concise and relevant.

If the person is digging into a 5 minute read on your checklist features I think this space would be much better used including the benefit by explaining how much time or money is made / saved using great checklists.

The benefit in the form of a business bottom line is implied, but they never take the last step. I’ll give two examples:

Here we’re presenting the feature of being able to copy / paste checklists. They broach the topic: “create them, save them (same thing), and use them repeatedly to decrease your workload” but I’d love to take the last step to a benefit, how much time?

And I’ll bet businesses get other benefits like accuracy—how many times have you created a checklist for a new project and left out a critical step? The best case result is that you’re embarrassed, the worst case result is losing a customer.

Use advanced checklists, save time, save customers, stay cool. Coca cola.

One more example:

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This is SO CLOSE.

We have an easy to understand feature and a raving customer quote. Just take the extra moment to be like “what was the cost of not having all these tasks in one place?” What direct benefit do I get as a customer by using this feature?

Beyond just being frustrating I’ll bet the customer spent way more time getting through their checklists, slowing down production and billable hours, especially if a critical task waiting for their approval sits in limbo.

There’s clearly a benefit to the business that could have been promoted.

Github

Github is no stranger to detailed customer updates, especially in the era of AI.

Because Github sells primarily to developers, we see a new tactic in their product update “GitHub Copilot Chat now generally available for organizations and individuals”: “customer language” in the form of quotes from their development team.

As you can see this is a serious quote, two full paragraphs from a very senior engineer at Github, with a specific real world scenario. Since Github sells to and is used by engineers, this stands in for a customer quote in a pretty compelling way.

Of the 1,000 words in the update, almost 600 are directly from their developers.

This is specifically a good approach for Github, but also generally good to get a quote from your development team. One benefit in frequent, detailed customer updates is building trust. It’s really hard to trust someone you never hear from, and hearing directly from the development team further builds that trust.

It’s like when the chef of a fancy restaurant comes out to talk to you.

Github also embraces being multimedia by including a video of the update as well since this was announced at their conference, they smartly included a 10 minute clip during the announcement:

While adding a considerable amount of work to the update, I do like providing the option for the people who prefer video, and for the distribution. This video is on YouTube with 81k views, and comments are open allowing them to get messages like this:

They could farm these comments for customer quotes, and since it’s YouTube there’s also plenty of complaints they could use to make some improvements.

A few final notes on Github:

• When talking about tech they increase clarity by addressing the common questions up front. For example, they specify that copilot chat is powered by GPT-4, which is a phrase likely everyone who’s familiar with copilot will understand, and, one that most people would be happy with. (of course with consideration to the wide array of opinions on AI technologies, no one is happy about everything.)
• Outside of this one post Github is on a schedule, constantly updating their blog with product updates and developments from the field, averaging 3-4 updates a month!
• I was surprised they weren’t explicit on customer benefits, AI tools for developers are prime to say “your company will save X money, Y time, and get through your backlog X00% faster.” They hit on it in the video “Even adding a small feature can take hours out of your day.”

This last point of not taking the final step to customer benefit is extremely common and drives me a bit crazy. I think to myself as companies release feature updates “what was the point of building this? How does this make our business stronger? Why are we here?”

Perhaps Github specifically avoids this language because developers hate being “sold” to, but there’s plenty of room for Github to walk up to that line.

Basecamp

Basecamp has made a name for themselves by constantly innovating on “the format” (for whichever “format” you can imagine.)

The way that they provide customer updates is no different.

They don’t really do product updates in the way that we can compare apples to apples, but they do so much right that I wanted to include their approach in my research anyway.

To start, they have a public page fotemr all their features, https://basecamp.com/features, which includes an intelligently organized and prioritized set of features, interspersed with customer testimonials:

Lots to love here, the copy is clear and concise (“project management’s greatest hits”,) multimedia via large product screenshots, and each link takes you to a larger, sometimes annotated screenshots:

The closest thing Basecamp has to a traditional changelog of customer updates is their “new” page, https://basecamp.com/new, which features large, beautiful, annotated screenshots of all the updates Basecamp has made over the past year:

This is a fairly brilliant approach, instead of posting constant feature updates, they’ve created a structure where every time you want to see what features are new, they get to take credit for all feature development over the past year.

I wish I would have taken a screenshot when this was “NEW for 2023,” but I think that this is the overall feature recap for their newest version of Basecamp (“Basecamp 4.”)

Since there’s no timestamping the reader is free to infer whatever they want, and one of those readings would be “this is all new functionality as of 2024.”

This is probably the best optimized page I’ve reviewed so far at giving a prospective customer that sense of wow that Basecamp is really turning out meaningful product improvements quickly.

There’s not much more here that conforms to the rest of my research such that I can categorize their approach into categories, other than to say that they’ve done something very cool, that very much works for 37signals, and perhaps has some transferable principles for the rest of us.

I can see two downsides to this approach, first there’s a lot more room to be more clear about customer benefits on each feature, and second this approach loses the sense of schedule for people to be able to stay up to speed with the latest feature.

The first note is a recurring theme, my position is that basically everyone can do a better job of connecting that last step to customer benefits. For example, Basecamp says the following about their todo lists on their features page:

‍‍‍This copy is super strong (I tried to pick a good one!) but I’m not sure that “sleep well knowing it’ll get done” walks us all the way to the benefit.

Perhaps I picked too good of an example, but I imagine that small businesses lose tons of time, money, reputation, and customers all to the root cause of balls getting dropped.

With a project management tool I’d love to see the impact on project completion with this and every other feature, presenting some version of products getting done more quickly with fewer people with happier customers seems like a direct way to let these features speak to how they benefit the bottom line.

On the second point (not establishing a schedule): they also don’t post to a Basecamp twitter account instead favoring their 37signals account. This provides some cool upside that they can post about features that tie all of their products together, but if you’re considering buying basecamp and want to see what the last three months has looked like from a development perspective, it might be hard to figure that out.

It’s easy to imagine they’ve tested this and realized that they can put all the week over week effort they’d put into having regular customer updates and spend that time once on a polished, beautiful, descriptive page that they only need to update once a major release.

Given how unique and beautiful the combination of the “features” and “new” pages are it's hard to argue with the overall effect they’ve created, and it's just as challenging to recommend emulating.

It’s uniquely 37signals in style and substance, which prompts the question: what’s the “uniquely you” way to keep your customers in the loop?

Mailchimp

Mailchimp runs some of the greatest hits that we’ve seen so far while also adding a few extra bananas.

We’ll start with their big, beautiful “What's new” page which serves as their entry point to learn about their product updates:

The button labeled “Try new features now” takes you right to the login page:

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This got a laugh out of me the first time I clicked it. My expectation was that I’d get more details on new features… but they’re right! I’m not sure what I expected, but if I want to “try new features now” logging in would be the way to do it.

Perhaps eclipsing that was my experience on clicking on the following CTA for “Draft emails with AI”:

Guess where the "Draft emails with AI" button goes?

Did you guess… the pricing page?

Researching Mailchimp reset my thought process on being direct and conversion optimized. Why was it my expectation that there should be steps in between “here is the feature” and just straight up using the feature, either by logging in or signing up.

If Mailchimp, a marketing automation company with near infinite incentive to create marketing content funnels you right to the login / sign up page, we should take notice.

Mailchimp's “what’s new” page also features (haha) a few other great multimedia touches:

• Large, well designed screenshots
• A video overview for the entire page
• A lot of “you” language, like “Respond to customer and client inquiries 1-to-1 in your Mailchimp Inbox” and “Let AI help generate emails and automations to welcome new customers, recover abandoned carts, and promote new products. You only need to review and send!”

One tactic that I’m not sure about is “Coming Soon” features:

Of the nine feature headers on the What’s New page, three of them are marked as coming soon.

My personal preference would be zero. Showing coming soon is a double edged sword.

It’s great that they’re providing a public view into the roadmap, however, trying to sell more than what’s in the product today can lead to heartbreak (when someone inevitably doesn’t read the “coming soon” part), or can cause people to second guess—should I wait until they have this new feature I really want now that I read it? Should I see if any of their competitors have this feature that I can use today?

This needs more research but my assumption is that very few people will say “there’s more features being added eventually? I’ll sign up today!”

Switching gears, let’s take a look at a more traditional product update, this is Mailchimp’s fall release 2020 update.

I’m a big fan of the comprehensive update style, I especially like the multimedia style with a video up top which supports the detailed sections below:

This is a nine minute video featuring their chief product officer and other execs within the company, showing how important customer updates are to them.

This is perhaps one of the strongest examples of a company showing through effort and attendance that the product updates the company is pushing is front and center to the leadership team.

The video also covers a rare product update tenant, which is covering the why behind these new features. This gets bonus points because it’s also directly adjacent to what business benefit a customer would get from using the new features.

Mailchimp’s overall goal is to make your marketing more effective, which provides a direct path for potential customers to understand how using Mailchimp makes you more money.

The video also speaks to their different user types between small business owners, marketers, and developers.

Each of the feature sections have some great “you” language in addition to links which take you to more details on each feature (which was my initial expectation on the What’s New page):

Overall a strong update. Light on specific customer benefits (how does this make us more money, how much more money does this make us?), but provides a concise description of what the company built and how it’s used by customers, usually with an accompanying screenshot.

In all my research I’ve been left wanting for more focus on the business impact of feature development, but their video is as close to being direct on this point as I’ve seen.

HubSpot

HubSpot has been credited with inventing (or at least popularizing (but I think they invented)) content marketing, and as such their website includes thousands of tactical posts ranging from how-to content, basic 101 style content, advanced tips, and of course product specific items.

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HubSpot’s customer updates start with their  “what’s new” page which shows (what appears to be) a chronological recap of their most recent three major features.

I love the layout they’ve used. Focusing on three major updates helps focus the current or potential customer coming to this page. Breaking each feature down into a title, short description, screenshot, long description, and a “learn more” link is a fantastic structure which we’ll come back around to in our templates section.

The overall effect is impressive, but, this is not an overwhelming amount of work for each feature release, finding that beautiful middle ground of impressive looking, fast and easy to do, and highly converting.

It’s unclear why “TikTok Integration” is a different color and adorned with sparkles. I’m guessing that this is their way of having a main or featured update of the three. Feels like overkill to me unless these are truly the three most recent updates and not curated. Three is curated enough!

One other note of interest: two of the three items (Webflow and TikTok) are integrations! They have no fear of promoting the “boring” stuff. It also seems that the Webflow app is in the Hubspot app marketplace, meaning the Webflow team built it.

This is a challenging play to recreate, but if you can ever find a way to get another business to build on top of your product, you promoting that work is win/win.

The company who built the integration gets eyes to the addon / app / content they created, you get the benefit of whatever they built plus customer update credit.

CommerceHub, the third “what’s new” item, is the newest “hub” in HubSpot. If you’re not familiar with HubSpot the way they’ve decided to keep a sense of sanity while trying to build around every department is breaking the product up into “hubs”.

The most popular hub is the marketing hub, which does all the stuff you probably think of HubSpot to do, landing pages and campaigns and whatnot. They also have a sales hub which is their CRM.

This lesson on HubSpot to underscore that a new hub is not a small amount of work, my outsider analysis is that the structure of the what’s new page might be one feature a “partner” has created, one feature that we’ve created, and then the most recent hub or other major section of the app we want to push.

It’s unlikely that this is one of the most recent features they’ve pushed because it’s quite a bit larger than a feature (ie, there’s lots of functionality within the commerce hub that could be promoted,) and that they were doing events around commerce hub ~4 months prior.

Unrelated, here’s a screenshot that I found researching commerce hub that I think everyone who’s ever spoken to a customer will feel:

Hubs are also a source of expansion revenue, so that could be a part of the analysis of how they construct their ‘what’s new’ list.

Below the fold is the “what’s new” section there’s a section for “release materials” where we can dive into a traditional customer product update.

For further analysis we’ll dive into the “November 2023 Release Notes.”

Off the bat the list of changes is huge.

I count 43 updates across 12 sections (mostly organized by hubs, but some that fall outside like mobile, app marketplace, and multi-hub updates.) This happens on schedule every month, so the impact snowballs over time.

If you’re trying to wow a customer or a prospect to show that your team is hard at work improving the product, 43 updates a month, every month is a great place to start.

Hypothetically if you’re frustrated that Hubspot hasn’t added 28 day billing cycles to the commerce hub? Well, it’s not like they aren’t doing anything! Even though that’s a simple feature request…

How do they get so many updates? They don’t ignore boring updates.

They do a good job of providing a concise update on each new feature, and since HubSpot has many plan tiers they’re explicit about who gets access to which new feature.

On the downside.. This list doesn’t feel prioritized and isn’t written with “you” language. For example, this is the first update:

“HubSpot has rolled out an update to our integration with Facebook's Conversions API. The Conversions API is designed to create a direct connection between your marketing data and the systems which help optimize ad targeting, decrease cost per action and measure results across Meta technologies.”

A good start would be to flip this, start with the fact that this new feature will help you decrease your cost per action while being able to better measure results—get more customers for less money with more confidence! This brings the benefit up front while also using “you” language.

With the update being this long they definitely could have gotten many more updates, and perhaps have separate places to see those updates.

The video is really great—great energy. Super strong way to be multimedia.

However, the list of features discussed is different from the post. And we’re still not talking benefits.

The first update discussed is conditional properties, which allows customers to filter one set of attributes based on the selection of another property, the example they gave is that if you set a customers country to Canada, the property “state/province” will automatically be set to just Canada.

This is really cool! But, I think it’d cut through just a bit better if they explained a bit of business value… what was the problem that got them to build that feature? I’m sure HubSpot customers lose TONS of money because of incorrect CRM data!

Overall Hubspot has found a great blend of highlighting their best “recent” updates (even if it’s a few months old) while supporting those cornerstone updates with a HUGE list of monthly updates, presented with text and video.  

Baremetrics

Baremetrics is a saas finance analytics platform best known for having a very handsome CEO from mid 2020 through mid 2023.

Secondary to that Josh Pigford, the founder of Baremetrics invented a number of tactics we see used, abused, and debated over today.

The main principle we see carried through is the idea of radical transparency, sharing not just roadmap items, not just feature updates, but the entire state of the business, which includes both the ups and the downs and the specific financial details of the business.

This makes a bit of sense when you’ve built a platform to show MRR, new customers, churn rate, etc, but I don’t think most people would say “hey… lets share all this info with the world.”

Nerds continue to debate if this is a good idea to this date, but Baremetrics needs to be included in our analysis of what a great customer update looks like. We’ll take a look at an early product focused customer update, and then for fun we’ll look at a transparency focused customer update.

Let’s start with Baremetrics, New Feature: Customer Profiles.

This is one of the oldest feature updates from Baremetrics, dated almost 10 years ago. Despite its age we see all the critical pieces of a great customer update.

The update is hyper concise, providing an exact screenshot and a clear description of what features are being added:

Just two sentences to completely cover an entire new section of the product:

1. Each customer gets their own individual profile showing you that customer’s individual LTV and MRR along with social and location information.

2. In addition, you can view the entire transaction history of that customer from signup to charges to failed charges and cancellation.”

They also do a great job of providing further examples without being prescriptive:

The pattern of showing real world use is fantastic. This is best by taking quotes directly from customers, but that takes time and effort, and our goal is to get meaningful updates out the door quickly and easily. Using a quote from an internal team member or “the company” instead can provide real world usage examples while getting the update out quickly.

To nitpick a customer update from 10 years ago, I’d focus on two things:

First, the update has a lot of “we” language, talking about Baremetrics both as the creator of the feature and the user of the feature. If you’re reading in order you’ll know that my goal is to include as much “you” language as possible, focusing on the problems your customers are experiencing, and how much benefit they get out of using the feature.

Second, the update doesn’t take the last step to business value. For example from the opening paragraph: “Baremetrics has largely taken a high-level approach to your metrics, showing you a 40,000-foot view of how your business is doing financially. Today, we’re bringing that view much closer and making it much more personal.”

Why are we doing that? What issues prompted Baremetrics to make this feature? And to what business impact? In my research the golden formula for a feature like this is [the problem customers had that made us make it], [what we did], [business impacts of that feature.]

For example, If I were to rewrite the opening to the update with these two points in mind, it might look something like:

“As a customer of Baremetrics you’ve already been able to see the high level effects of business changes on your metrics, like what a change in pricing does to ARPU or what impact a new feature has on retention.

But, we’ve heard from our customers that not every change is so clear from the high level, what happens at the individual customer level has a huge impact on our ability to effectively pilot our business.

So today I’m happy to announce customer profiles, the ground level truth on each and every one of your customers, making sure that as you make changes to boost new revenue, create more expansion revenue, and decrease churn that you can track the impact of those changes down to a user level.

Anecdotally with the additional information gained from customer profiles we were able to troubleshoot why a specific type of customer left Baremetrics, improving our churn by .5% which will add up to a six figure impact by the end of the year. And it’s just month one!”

Something like that. I understand that it’s about 250% larger than the original text, but it’s sort of my move to increase Baremetrics' things by 250%.

The point is that we start with a business problem, we discuss quickly how we solved it, then we finish with outcomes. We should use as much “you” language as possible in order to help current and potential customers visualize what giving us a few bucks will yield to them in return.

As an extra bonus, let’s take a look at the most popular blog post Baremetrics had during my tenure: I Sold Baremetrics.

Since this isn’t a traditional product focused customer update I’ll keep it short here (says the dude writing 10k words on customer updates.)

A few highlights:

• This post is an example of a great way to provide a major customer update, quickly, in a way that they’ll understand.
• He’s very clear on the specifics, including the information that everyone wants to know (eg, how much??)
• For a potential bombshell he provides the bottom line up front: I’ve been building this thing for 7 years, I’m selling the business. Also… the title is “I sold Baremetrics.”
• The post tells the story in a very honest way (eg “this rollercoaster reminded me of all the things I don’t love about running a company.”)
• He also includes “the future of Baremetrics”, which in keeping with the theme of this article is the “you” language people will most want to hear (after the acquisition number)

Reference companies without complete research

I used (quite a few) more companies in my research, here's a short list of a few of the other companies referenced. If there's interest and requests I'll happily release another round of research with best practices.

Here's that list:

• WP Engine, see “WP Engine eCommerce Hosting—Now With Stripe Connect!”
• Signwell
• Dingboard (great example of updates integrated into the product)
• Intercom
• Transistor
• SendSpark
• Notion
• Sprout Social
• OpenAI
• CleanShot

Act 3, The Science of great updates

Through matrix multiplication of our research set we can generalize a set of rules for our customer updates. 

There are two sets of lessons to learn. 

First, how can we create more customer updates? The goal is to fill the changelog with useful, interesting updates, thus reminding our customers of our hard work and fostering dialogue.

Second, how can we improve the quality of these updates? We want to identify the characteristics that the best updates use to efficiently communicate product improvements. The goal is to increase the frequency of updates without spending more time on them than the product improvements themselves.

As a reminder, achieving these two goals helps our business by:

• Preventing churn
• Increasing new customers
• Boosting expansion revenue
• Setting up for a price increase
• Building trust
• Earning referrals and testimonials

(If you need more convincing on that, re-read the “Why should we?” section.)

In order to get all these benefits for our business, we need to frequently ship great customer updates.

Here’s how:

The principles of more updates:

1. Being on schedule
2. Being public
3. Being concise
4. Including the “boring” stuff
5. Including the “bad” news
6. Being relevant

The principles of better updates:

1. Using “you” language
2. Being multimedia
3. Including customer quotes
4. Being clear
5. Including the benefit

(+ a few bonus tips)

The principles of more updates

Put simply, most companies do not update their customers enough. The 40th-percentile company doesn’t update their customers at all. 

Providing any form of regular customer updates places you in the top half of companies, akin to the way any return on investment positions a VC in the upper echelons.

Consider our earlier tweet about investor updates:

To directly apply it to our domain

• Updates only when there’s a big issue = mediocre business
• No updates = 90% chance of death
• Short updates w/ customer benefits = business will succeed

With this in mind our research identified several techniques used by companies successful in maintaining a high velocity of updates.

Being on Schedule

In a high-velocity update environment every decision to publish an update can feel like hitting the brakes. Figuring out the perfect timing for sharing news is a double-edged sword. 

On one hand, you’re caught up thinking about the best time to drop an update, which eats into the actual time you could be polishing the announcement. 

On the other hand, you’re chasing down all the dependencies, like the details of the new feature that’s shipping, customer testimonials, or the perfect screenshot. Scrambling for these details last-minute when you’re supposed to go live is not ideal. 

Here’s where a little planning goes a long way. Sketching out a timeline in your head – or a mental Gantt chart, if you will – helps ensure you’ve got everything ready for launch day. . 

Plus, sticking to a schedule can actually sharpen your updates, making them tighter and more focused. Think of it as borrowing a page from the agile playbook: we tailor our updates to fit the time we've got.

Finally, having a schedule gets you into a rhythm. I swear to you as the person who’s writing thousands of words about customer updates, I would have PROMISED you that I was doing updates every two to three weeks for a product I was building. 

I would have made an oath to you that was the case. I would have bet a significant amount of my net worth that I was sticking to that timeline.

But here’s how it actually went down:

The timeline was:

• Aug 24th, Initial intro video
• Aug 28th, got my blue belt (unrelated, but pretty cool)
• Sept 18th, update one
• Oct 25th, update two
• Jan 2nd, update three

Since my schedule was “when I felt like it” I sent four updates over six months. This turned out to be almost one update a month, with updates coming almost at the end of every month. Which, in hindsight, sounds like a reasonable plan!

But the reality was more hit or miss, with updates being published inconsistently throughout the month, or, sometimes not at all. 

Now that I’ve researched customer update best practices I’d handle the scheduling of these updates much differently. The main change I would make is setting a schedule to publish an update every two weeks. This is how frequently I thought I was publishing updates before I checked, and the difference in frequency is stark.

The once every two week schedule would have provided 12 updates to customers over this timeline, while my inconsistent schedule only published 4.

Don’t be like me. Set a schedule. Save lives.

A great example of a company that publishes on a schedule is HubSpot. They have an evergreen “what’s new” page which features three recent updates, a monthly cumulative release notes blog post, and a monthly presentation shared publicly as well.

Sprout Social is another great example. They include a monthly view of their product updates, and a day by day drill down view. I love the commitment to show updates on a monthly cadence, but also keep track of the daily view. This shows a huge internal focus on customer communication – and on shipping! You can’t document thirteen updates in the month of December without product updates being a priority.

Being public

An interesting finding from my research was that many companies didn’t do any sort of regular updates. Some were in the habit of weaving product updates into their main blog (totally fine,) but others ONLY published product updates to internal customers, either through in app banners, embedded widgets, or just via a customer only email list.

There’s two reasons this happens.

First, they make the assumption that only current customers care. Rationally, if they’re announcing a certain feature is faster, or some bug is fixed, if you’re not currently using the product why would you care? The potential customer has no basis for comparison, and probably doesn’t even know why it’s important that something is fast or that that bug is fixed.

“Why tell someone that something is better or fixed when they have no basis of comparison?” they ask.

Second, there’s a self esteem issue. Companies, especially early stage companies, can be embarrassed they had the issue in the first place. For example, if they improved the performance of some key feature, they think “that means it was too slow in the first place.” A fixed bug promotes the fact that they had the bug in the first place.

This is of course true.

These companies are not dumb, announcing that a bug is fixed may alert people unaware that the bug existed. This doesn’t mean the company is not completely irrational.

They’re just a bit socially awkward :).

To address this directly: every product has bugs. Every team ships software that needs to be improved. Most products are more wrong than right at launch.

The difference between you and the rest of these losers is that your team is putting the hard work in to flip the ratio from mostly wrong to mostly right.

A customer who is a normal functioning member of society will be glad to see that the product is faster. They’ll be happy to see that bugs are being fixed, especially if they were affected by it.

We’re also hyperfocusing on the updates that potentially could be seen as bad things. We also ship improvements! New features! Super powers!

There’s an art to sharing updates with customers that might not be immediately seen as positive, especially by including the benefit (read more below, I promise there’s examples of how to turn what seem like bugs into updates customers will love to read.)

You also need to accept that some dissatisfied customers will respond negatively to any update.

If you build a feature other than the one they want, they will complain. If you fix a bug that’s not their main bug, they will complain. If you fix an issue that was their biggest concern… they will complain that you didn’t do it sooner!

These are the loudest voices, and I can see why if you’re not committed to customer updates why this immediate negative interaction would scare you off. Keeping the long term view and understanding the benefits of having your updates be public will help you weather the storm.

To summarize, one of the key reasons to do frequent, well written customer updates is to increase the number of new customers you get. If you don’t share these updates publicly, you’re not getting credit for the hard work your team is putting into the product, and you’re not even getting credit for the hard work you’re doing on writing the customer updates.

To be totally binary, if you aren’t sharing customer updates publicly there’s no way to get marketing and sales lift out of customer updates, meaning you get zero new customers from these efforts.

Great examples of being public include… literally every company researched in this article. Sorry, it’s really a very good principle, if your updates aren’t public I’d sort of recommend you do so.

Just for form I’ll give a shout out to Github for the publicness of their updates because they also include internal engineer quotes in their updates, giving further insight into their thought process, and to OpenAI for including both a weekly view into their platform changes AND a look into their internal politics (remember that one time that Sam Altman got kicked out of the company? That was crazy.)

Being concise

The strongest weapon in the “more updates” arsenal is being concise.

I fully appreciate the irony of this advice in this delivery mechanism.

As people who are focused on their craft we feel the urge to create lasting structures. This often means providing context through related information, teaching through other examples, and the creation of a meta narrative—making our updates into episodes of the series that is our company.

I CLEARLY get that. And, if you can do all of the above while sending customer updates on a weekly basis, go for it. But if you can’t do both, we’ve seen the best of the best strip out the pretense and send simple updates on a regular basis.

Here’s why that extra context might be fluff.

First off, only a small percent of people will fully read an update. A potential customer might not read the updates AT ALL, but instead just look for the number of updates to answer “is this product maintained?”

Second, the people who do read it probably don’t need context. See “keep it relevant” below for more on this. For now just trust me.

There is some value in reminding people about benefits, we’ll talk about that in including the benefit, but do an internal audit and ask “is this fluff?” If the answer is yes, congrats, you found an opportunity for efficiency.

Look at the updates from HubSpot, Sprout Social, and Open AI.

HubSpot:

‍

Sprout Social:

‍

OpenAI:

‍

Simple ships.

Including the "boring" stuff

The leading reason that companies don’t frequently update their customers is the idea that they didn’t do anything interesting.

This is a similar mentality of not being public. It’s lacking that touch of confidence that if you decided to work on it, it’s important enough to talk about. If you introspect and realize that truly no one cares and no one benefits from the things you’re working on then it’s truly a remarkable result of forcing customer updates that you make better use of your time!

In reality it’s hard for an improvement that customers experience to be too small to write about.

Perhaps bumping your ruby version from 3.1.0 up to 3.2.2 might not be noteworthy*, but even the small bug fixes and minor improvements are noteworthy. The goal is to show a constant pulse, the heartbeat of our product.

We should take credit for all our work.

(* however, updating to this version of ruby fixed a few security issues, closed dozens of bugs, improved performance, and provided new language features for the team to use… sounds pretty material to me! So if a Ruby version bump feels noteworthy, whatever small improvement you made is too.)

Then the question is, how can we make these boring updates newsworthy?

First, I just told you they’re not actually boring. Stop that.

When Slack wrote in their update “Admins can delete private channels”, do you think they were thinking “oh, this is too boring to include.”

Wrong. This stuff matters to our customers, and even if the user reading the update isn’t specifically impacted they will take note that things are getting fixed, and that’s a good thing.

Second, we strip down some of the boredom by choosing our words correctly. This requires us to move past step one and believe internally that this is an interesting update, and in that case “Fixed crappy slow code” becomes “Improved speed for customers, you should find (activity X) to be much quicker, getting you to (benefit) faster than ever before.”

I’ve had this conversation many times. Teams don’t want to announce bug fixes, especially if the bug has been around for a while, because you feel like you’re drawing attention to the bug.

First off, not looking at the bug does not make the bug go away. Secondly, your customers know about the bug, they reported it.

Lastly, they’ll be happy to see it gone!

A great example of boring done right are the updates included from our Slack research, followed by HubSpot.

You will be amazed what impact a positive attitude, a bit of copywriting, and a deadline will do for your ability to ship tons and tons of customer updates.

Including the bad news

Similar to not including “boring” updates, many companies will shy away from what they think will be received as bad news.

A great example of this from the research is Slack dropping support for IRC and XMPP:

You might not remember this happening, but at the time it was a BIG deal. People were pretty upset!

Slack had the option to put this update outside of the normal stream, or, not say anything at all.

But instead they looked at the issue, evaluated their options, made a decision, and then faced it head on. Not only did they make the decision, but the language in their update is unequivocal: the gateways are now closed. There’s no way to read that and not know that it’s GG for IRC.

Including this bad news in their standard updates allowed them to get ahead of the conversation by explaining their reasoning (can’t support our features), and allowed them to head off the biggest area of real concern: accessibility.

A lot of time we think of our product as a collection of lines of code, collected in a repository and deployed to a server. However our product is much more than that.

It’s our goals, it’s the way that we think the world should be, it’s the research we collect, it’s the taste of the people making the product, and as a result it’s the collection of decisions we make as a team.

We agonize over these decisions internally, these choices ARE the work, and you should get credit for your work.

Here’s a bit from Jason Fried to increase confidence in your judgment:

‍

Keep it relevant

Writing fewer things is faster than writing more things.

Irrelevant information is a thing that requires writing.

Therefore, Socrates is a dog.

Generally it’s not the goal of the writer to provide irrelevant information (and yet we do.) Generally this is packaged in the format of wanting to provide more context or additional examples.

There was some class we all took that taught us that we need to provide three examples for everything, and that’s generally what we tend to do in a business context.

However, the strongest updates are just the distilled essence of what benefit the customer is getting, including some AMAZING one line customer updates.

As an example, the Trello update for the “advanced checklists” feature set has a quote from The Checklist Manifesto on why checklists are important.

This is a great book that I recommend reading, but do we really think that the people who are likely to be interested in “advanced checklists” don’t already know why they’re important?

Quantity has its own quality. If you’re writing updates frequently you don’t have to fluff by adding quotes, referencing books, or even adding too many memes.

As an aside: I’ve heard teams say they have “no time to write updates” a hundred times. I’ve never once heard “we don't have time to meme.”

Having the pulse of relevant updates can be a starting point, there’s always the chance to create rollup updates (more below) or to add some additional media. Hubspot and Github do a great job including videos with their updates.

Great examples include the Hubspot monthly updates where they comfortably provide many one line updates in their monthly recaps.

It’s OK to stay focused.

The principles of better updates

Using "you" language

You’ve seen me refer to “you” language a lot in this piece.

I thought I made this phrase up, but as I started to dig into the entomology, evidently there’s the concept of “I” vs “You” language in the field of couples counseling… whoops.

It still makes a ton of sense here, I’m going to roll with it and I’ll talk about the ramifications with my therapist.

All of the best updates included this “you” language.

The features, benefits, and even motivation to build the thing in the first place is based on YOU, the customer, and not “I”, the company / team / developer / marketer that did the work.

Remember: the goal is to remind our current customers why they’re paying us and to get new customers to sign up. The gold standard is “YOU will now be able to do thing X,” or even better “YOU will make more money because you’re getting benefit Y.”

Here’s some quick examples to drive the point home.

Great “you” language:

Transistor.fm:

‍

Sendspark:

‍

Intercom:

‍

Even in this article, see how I’ll say stuff like “my research, my experience, my companies…” isn’t that annoying? Don’t you just care about how you can improve your business and solve your problems to make more money?

This is exactly the spirit of “you” language.

Being multimedia

If you skip this tip because you think it’ll be too time consuming: understandable, have a great day.

For those of us interested in going maximum effort mode on updates, going beyond text is a great way to catch a wider audience for your updates, go into greater detail, and frankly to show off.

Most of the big tech companies provide a video update alongside their text updates, so if we want to look a bit bigger than we are we can copy off of them.

I’m personally a fan of video since you can get across a ton of information, control the flow (ie, people not skipping around), and you can get across some of your personality too.

I generally record a video for each launch and update, you can find all of them on my twitter highlights. Whenever I launch something you’ll see this goofball face staring back at you:

‍

Everyone has their own style, but I like to include some sort of upbeat background music, a slideshow to keep me on script, and a live demo of whatever I’m showing.

Some people go even further, recording podcast episodes on their updates, creating infographics and charts (which are also nice for the sales / marketing team to share), and the biggest companies throw full on events for product announcements.

This is definitely more work and if you’re having troubles getting updates out the door frequently I’d skip this step in a heartbeat. However, if you’ve got a great update that makes customers want to buy, it’s not a bad idea to go multimedia and squeeze the maximum juice out of it.

Include customer language

It’s one thing for you to say how great an improvement is, but it’s such a larger statement when you have a customer quote in a product update.

It says two things, first that the thing you did actually helped at least one customer, AND that the customer cared enough to provide a quote.

If you’re already doing a good job getting updates out the door, getting these customer quotes might be easier than you think. When a feature is requested or a bug is reported, capture the specific words that customer (or lead) says.

When you fix it you let that customer know (you do let them know, right?), generally they’ll respond and let you know if it actually worked or if you still have problems to fix.

If it’s fixed they might have already gone above and beyond with their language, saying “this is going to make my daily process 5 times faster!!” Your job is easy at that point, you say “Awesome—do you mind if we add that quote to the product update?”

Conversely if they just respond “great, fixed” you can ask them to elaborate with a quote if they don’t mind. You can provide a tshirt or some other token of appreciation… but that’s a topic for another day. *

If you don’t have that open dialog going with customers another great standin is providing quotes from people on your team.

Generally this is used by companies like Github, where they frequently quote senior members of their development team. I think this might work with other roles, but for whatever reason developers tend to be regarded as being fairly anti sales and marketing, so promoting a quote from a developer might seem apt where a quote from the CEO may seem disingenuous.

I have no data to back that up other than seeing press releases from fast food companies that feature quotes from their CMO.

The vibe is like “yeah VP of Marketing of Dunkin Donuts… of course you think the Salted Caramel Creamer is great and ‘wanted to bring that same excitement to the at-home coffee experience’”.

Feel free to experiment. Getting language from a real customer is the best case, but even a stand-in quote from a persona might help frame the update from the perspective of a customer. An internal quote can also provide needed context and trust in the process.

Ultimately our goal is to show that what we’re building matters to a customer and solves enough of a problem that they’re willing to take time out of their day to write about it.

* This is getting a bit off topic but you can even get customer quotes when something breaks. Stripe did this with me when they accidentally took too much money from me way back in 2013. They explained what happened, said sorry, and asked if I wanted a shirt! Happy ending for all.

Being Clear

This is a similar mentality of not being public

Clarity is the gift we give our customer negative words at a time.

Being clear helps us, because fewer specific words are less things for us to type, speeding up the process.

Being clear helps your customers because they are not interacting with our updates in a sensory deprivation tank. Everyone is in their own world with their own goals, dreams, and hurdles to overcome. Being clear helps your customer quickly scan your update and move forward with their day empowered.

Being clear generally requires two things, picking a set of words to use and simplifying concepts.

While “picking a set of words to use” literally describes the act of writing, what I mean here is that there should be a few key phrases which and unambiguous and that your customers will understand.

I’ll give an example from my history, my first real business was called TeamPassword, it’s a password manager for teams. So far so good at picking a limited set of words.

One of the hardest naming challenges we had was “what do you call the things stored inside the password manager?” I just used the obvious option, it’s a password manager, they’re “passwords.”

The hold up on that reasoning was that each record included a title, url, username, password, and notes. Does it make sense to call the whole thing a password when it contains a password? Would that cause confusion when they put in a support ticket with a password issue? And since passwords are shared on teams, would that cause internal confusion?

“I need the login info for that account, I don’t have answers to the security questions.”

“Yes, I just shared the password with you”

“... bro.”

There’s usually tradeoffs in what words you pick, the important thing is to pick a specific set of phrases and stick with them.

A side note for the curious: We decided to use the phrase “logins” in TeamPassword to refer to that combination of fields. There were shared logins and private logins, and logins could be categorized by a group. This still caused a lot of confusion and I wish we would have just called it the technically incorrect yet intuitive “password!”

For clarity through simplifying concepts we can rely on a few of our other principles. Including the benefit (directly below) is a fantastic way to bring about clarity, not much mental energy is required when you’re saying a few words about how you’re helping them.

Including the benefit lets you cut a lot of the fluff, too. If you’re completely focused on communicating the benefit of a feature to your customers you can skip the story about how this feature came to you on a hike, how you struggled to choose the right database, and how your lucky yellow socks really brought this thing together.

There’s a joke that I tried to find to illustrate this… it’s basically someone being really long winded and providing irrelevant information to the listener, and the punchline is as they go to walk away they’re like “Oh, right, by the way your house is on fire.” If anyone can point me in the direction of what joke I’m thinking of I think that’ll really bring this piece together.

Actually, I’m talking so much about including the benefit, let's just get into it.

Including the Benefit

I saved this one for last because basically no one does this. Taking this last step to customer benefit is the secret jutsu / forbidden spell / limit break / ultimate ability of customer updates (depending on what type of nerd you are.)

When I say “Including the Benefit” I mean spelling out how exactly the change that you made will make your customer’s business better. If you’re not sure where to start, the closest resource I’ve made in the past is the “five pillars of growth” published through Baremetrics. This is focused on saas businesses, and the TL;DR are that the five pillars are:

1. New customer revenue
2. Expansion revenue
3. Reduce churn
4. Reduce downgrades
5. Increase reactivations

This isn’t the worst place to start when thinking of the benefits you can pass on to your customers.

Through using your product, are your customers going to get more customers? Can they increase expansion revenue? Are you protecting against the downside of churn and downgrades? Or can you help them get their customers back?

This can take a bit of creativity, which is ok!

For example, one creative interpretation is that saving a marketing team time on a routine reporting task gives them more time to focus on marketing, scoring more new customers for their business.

Similarly, improving some aspect of marketing reporting may help the marketing team identify which channels are converting, decreasing cost of conversion and acquiring customers more effectively, which either means more customers for the same budget, or the same number of customers for cheaper.

There are lots of reasons customers churn, but goofs, gaffs, and f-ups is a sure fire way to burn customer loyalty. Any feature you deploy that prevents customer facing mistakes can be targeted at keeping customers happy.

The goal here is to “take the final step” and tell your customer exactly how using your product is making them more money than not using your product.

(One funny note, you might also try to include the benefit and realize… the updates we’re making will have no impact on our customer’s bottom line. That’s not good, and by focusing on this question perhaps we can do a bit of a better job with our roadmap.)

Remember the different audiences reading your updates.

Too many people assume the only audience for updates are the power users and oldest, most entrenched customers. Brand new customers who have ZERO context read the updates. Prospects and trial customers read the updates to see if this product gets improved. Anyone you’ve increased pricing on will scour the updates to see if it’s justified.

Don’t make them work for it, tell them right up front how using your product makes their business better.

Examples are in limited supply, but this update from Transistor FM does a great job:

Why aren’t all updates this clear?

“Add another income stream” !

Aka “you will make more money” which is what all of our customers want to hear.

Bonus tips and tricks

These are our hail marys (hail maries?), the tools we can pull out of our back pocket when we’re in a bind.

Often we need to have the team “go long” when we’re sticking to our schedule but we legitimately have nothing to talk about. Sometimes you need a “touchdown” but haven’t… done the yards? Sorry, they haven’t made an NFL anime yet so I don’t really know the rules that well.

So we’re on our schedule for an update and have nothing in the hopper, what can we do?

Our first option is to feature some “popular updates” in addition to our chronological updates. You can see these callouts on the customer updates pages from both Trello and Hubspot. I think this is generally a good idea even if you have something to talk about, but featuring a previously popular update on the week that you don’t have anything else to say might just be a convenient solution to our lack of update problem.

Another option is to do a round up over a longer timeline. Basecamp’s “new” page is a great example, showing how they highlight all the new features of the latest version of their product. The “new” features are all the features included in the latest version, which I’m sure they must have worked on for many months (or years) to build.

A smaller option would be a “best of” for this month, quarter, half year, year… and if you burn through all of these and still have nothing to say go for “best of all time.”

Another option is to roll up groups of features into one post (like our “advanced checklists” post by Trello.) One of our guiding principles is getting credit for every single line of code you write, but by doing these feature roll up posts this is actually like double credit, which feels like cheating.

If you have time to focus on making an update but no update to write about, another option is to feature a customer’s usage pattern or specific use case. The contents will be different but the approach is the same—figure out a usage pattern in the product and highlight it sort of like it’s a feature.

For example if you found out a customer is using the dashboards in your product to make important and lucrative decisions, that could be its own product update (“Become a millionaire with you dashboards.”) I’ve had superusers on every product that have shocked me in the way that they use the product, it’s always fun to show how engaged some customers are and share their pro skills with other customers.

The same is true for a specific use case as well. For example, if you have a cross section of customers who own marketing agencies, thinking about the “Driving new customer acquisition as a marketing agency” update is a solid way to fill the space.

You could also just generally get a customer shout out. I can’t take credit because this was done after I sold the business but this is an amazing video for a customer of my last company TeamPassword:

Beyond that… you just gotta vamp.

It’s jazz baby!

Do what you need to do to stick on schedule, and let this chilling time inspire you to get those customer updates planned in advance.

The Templates

This guide includes a pretty wide array of tips, tricks, rules, mantras, schemas, and blueprints. Trying to smash all of those into one simple template that’s short and concise but also includes benefits, and boring stuff, and bad stuff…

You can see that it can become a mess.

As they say: there is no perfect tomato sauce, only perfect tomato sauces.

Here’s a few quick updates you can use mad libs style to spend zero time thinking about structure and 100% of your time writing awesome customer updates.

So existing customers stay longer and new customers sign up. You get it.

Update Templates:

• Big Feature Update Template
• Customer Request Update
• Bug Fix Update
• Whoopsie Update
• Rollup Update

Big Feature Update Template

Customer Request Update

Bug Fix Update

Whoopsie Update

Rollup Update

Closing

We’ve been through a journey together.

The original idea for this piece was a short, SEO focused article that would transfer a bit of knowledge and build a bit of awareness for the work we’re doing around automating customer updates.

As I started writing I realized that:

1. I have a lot to say about customer updates, and
2. SEO focused short term content kinda sucks.

We’ve all searched for things, landed on the top result, only to realize that the article just restates the question 10 times and maybe answers the question.

This drains the world of time since every reader is paying the 5 minutes of time reading an article that took them like 30 minutes to write. The balance flips after 6 people read the article, which sucks.

I realized in creating this that we severely lack “maximum effort” content, where I want to drop 200+ hours reading, researching, writing, and rewriting. I want to deliver that in a format that a reader can skim through and have them leave with a careers worth of ideas and context.

Hopefully you feel that way. If you don’t please let me know.

To close out the key concepts of this article, here’s a mega TL;DR:

1. We should get credit for every line of code we write
2. Companies, especially early stage tech companies, are roasted for spending all their time on product and no time on marketing. Not updating your customers is what this looks like in practice.
3. Most companies don’t update their customers frequently enough.
4. Most companies are not explicit about the business benefits they’ll get from using your product.
5. Of the companies that do publish updates, too few of them realize that it's marketing to all audiences, beyond just our current customers to prospects and leads as well.

My mission in the proceeding ~70 pages is addressing these points so you’re in the top 1% of customer updaters.

If you’ve made it this far I’d love to hear from you, specifically on:

1. Did any part of this document stand out as particularly good?
2. Did any part of this document stand out as particularly bad?
3. What do you think is missing?
4. Do you have any great examples that I’ve missed?
5. Any other feedback that springs to mind as you read the document.

Acknowledgements

This beast of a document started as a short, SEO focused article. It would not be in it’s final, completed form without ~200 hours of research and 10,000 more hours of distilled career advice from the following people:

• Jason Cohen: https://twitter.com/asmartbear
• Paige Harriman: https://twitter.com/climatepaige
• (Coincidentally Paige had Jason on her podcast, it was great! Check it out here.)
• Walter Chen. Check out his company: https://sacra.com/
• Jason Gilmore: https://twitter.com/wjgilmore
• Alexandru Golovatenco: https://twitter.com/AlexandruGlv
• Josh Pigford: https://twitter.com/Shpigford
• Clay Collins: https://twitter.com/ClayCollins
• Ryan Kulp: https://www.ryanckulp.com/

Please thank them over the internet as I could not have done this alone!

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