When I arrived at Wildbit in 2016 as Postmark’s first product manager, my initial job was to work with the team to create a formal vision and strategy for the product. I wrote about that process in How we built a product vision and roadmap so I’m not going to spend much time on that initial process. The focus of this series of posts will be on how we redid the Product Strategy 6 years later—and how we did it together as a team. I am hoping this will be helpful as one way to approach this work in your own teams. But first, a little background.

As a small team (<30 people) working on a bootstrapped, profitable product we were lucky that the Product Strategy we came up with for Postmark in 2016 remained remarkably consistent over the next 6 years. We made some tweaks along the way, mostly to the ideal customer journey, but the fact is that it worked, so we didn’t need to keep revisiting and pivoting over and over. That, however, changed in 2022 when Postmark was acquired by ActiveCampaign. The entire Postmark team moved over to ActiveCampaign and we are still working on the product together.

For the most part Postmark operates as its own business, but we also recognized an opportunity and responsibility to revisit and update our Product Strategy to align better with the broader ActiveCampaign vision and goals—and include plans for integrating the two products. We are a team that loves to work collaboratively and get input from everyone, so we really wanted to create this strategy together. To do that, we broke the process up into 3 phases:

• We started with some async work to clarify the framework and goals, and gather feedback from everyone about the changes we needed to make to our current strategy.

• We had an in-person retreat coming up in September 2022, so we planned to discuss each element of our strategy together and come up with some rough concepts that we could refine afterwards.

• Our leadership team then had the responsibility to solidify the strategy and share it back with the team and ActiveCampaign leadership for final feedback before we could call it “good for now.”

There was another part to this. We are big fans of “working in the open”, so we we felt that we had an opportunity not just to do this work as a Postmark team in isolation, but also to share our journey with anyone in the larger ActiveCampaign team who might be interested. So we created a space in Confluence where we documented our process as we went along.

I highly recommend this approach because it has the added benefit of building up “organizational memory.” If we were to come back a year from now and go “wait, why did we decide to do that?”, we will have a record not just of our decisions, but also the context and the journey that led to those decisions. This is often severely lacking in strategy work, and I believe it’s one of the main reasons why strategies seem to change so often in some organizations. If no one knows why a decision was made, the next person to come along can very easily change a strategy or a direction without having the necessary context about the work that has already been done. In short, learn to love documentation! But I digress. Let’s get back on track.

For this series of (hopefully weekly) posts, I plan to cover each phase of our process separately:

• Part 1 (this post): Background and overall process.

• Part 2: Product Strategy purpose, framework, and async pre-work.

• Part 3: In-person collaborative Product Strategy work.

• Part 4: Refining and publishing the Product Strategy, next steps.

One more thing before I close up Part 1… I will talk about Molly Graham’s “black hole words” in more detail in Part 2, but there is one term we had to define right upfront. Since the “Product” in Product Strategy can mean so many different things to people, we wanted to be clear on the definition right from the start. Postmark is heavily focused on product-led growth, so we clarified in our documentation that when we use the term “Product Strategy” we don’t mean only design and product experience. We mean everything that goes along with that as well: product marketing, growth marketing, sales, customer success, scaling and reliability… the whole deal.

And with that… I’ll see you in Part 2 where I’ll talk about the Product Strategy framework we chose to use, and how we collaborated asynchronously to lay a solid foundation for our in-person retreat work.

What I’m reading

Jeff Patton writes about balancing conflicting goals in product development, including:

• Customer problems aren’t business problems

• We can’t directly solve business problems

• On time delivery doesn’t lead to customer or business success

• Focusing on business success alone is harmful

• Focusing on customer success alone is harmful

• Aligning our purpose with our organization’s purpose is really what motivates us

He walks through each of those moments of tension in detail, with some advice on how to navigate that. I also love this paragraph about purpose and motivation:

We make things that people use. When we’re doing it well, those things make people’s lives better. And, when we’re doing it really well, the value we create for our customers and users results in the business impact that sustains and grows our company. It’s motivating, fulfilling work.

I wanted to spend a little time talking about the Mastodon social network and its viability as a “Twitter replacement”, since this is space that’s really interesting to me. In a new post M.G. Siegler vocalizes the viewpoint that a lot of people have, which is that Mastodon is terrible and it will fail:

While it’s impressive that millions of users have apparently given Mastodon a try, the product is far too slapdash and clunky to keep folks engaged.

I agree that right now the product is really clunky and complicated, but that is changing fast. iOS app Ivory is in Alpha and looking great. The Mammoth app is running their own server to make sign-up easier, and I imagine more apps will start to go that route. User-controlled, abuse-resistent quote-boosting is actively being discussed.

I think the mistake people make when talking about Mastodon is all tied up in the search for “the next Twitter”. Please, let’s not do that. Let’s not give another social network as much power and influence as we gave that site.

If the criterium for Mastodon to succeed is “it creates as many main characters as Twitter did”, then yeah, I agree with Siegler that it’s never going to get there. But if, instead, we think about it as smaller communities, loosely tied together? I think then we might be on to something. Connection > Scale.

Anyway. We can connect on Mastodon if you’d like!

Some stray links

• 💀 Welcome to Dead Week. “[It’s] a week off from the forward-motion drive of the rest of the year. It is a time against ambition and against striving. Whatever we hoped to finish is either finished or it’s not going to happen this week, and all our successes and failures from the previous year are already tallied up. It’s too late for everything; Dead Week is the luxurious relief of giving up.”

• 🏡 Lots of excellent points about online communities here: A community isn’t a garden, it’s a bar. “The most obvious way an online community is like a bar is that bars serve alcohol, and alcohol makes people loud and stupid. It actually depresses your hearing, so you can’t hear yourself talk as well, so you speak louder. And a room full of people speaking louder means a very boisterous room. And of course, alcohol reduces inhibition, so you say things you might not usually say.”

• 📱This week’s useful app → Dato is a neat MacOS menu bar app that gives you a local clock, date, multiple world clocks, and upcoming events in the menu bar. A great way to deal with call times across multiple time zones!

• 🤨 This week’s WTF link → Get ready for ‘thaw and eat’ foods. “From frozen sandwiches that don’t need to be nuked to pies and waffles that go from freezer to plate, food manufacturers are racing to introduce products in the nascent ‘thaw and eat’ category.”

• 👴 This week’s Gen X link → In a Future Filled With Electric Cars, AM Radio May Be Left Behind. “Carmakers say electromagnetic interference causes static and noise on AM transmissions, annoying customers.” Sad!

• 📈 Last week’s most clicked link → Pika, the web app for creating mockups from screenshots.