Hi @natalie, have long admired you and your husband for a solid business and knowing what you all are going for! Congrats on your 20th birthday!
I’m curious about the following, can you walk us through:
How you structure your teams?
i.e. Do you have a product manager? How many teams do you have? How do you all work together with your devs/UX team?
How do you make product decisions?
i.e. How do you all prioritize items to be worked on? How do you ensure that the offering continues to be competitive and relevant to your users?
I would like to understand more on the balance between building a “people-first” business and the “beast” paradox. We always had attempted to build a “people first” business, but at the same time the business itself being the anchor point to execute this makes the beast grow, i guess.
What are your inputs to balance it? and how do you measure yourself not to cross the line either way and to build as a culture within the organization which is naturally aspirated to high-performance.
You’ve mentioned on multiple occasions how you’ve not spent a lot of time thinking about ‘marketing’ at Wildbit over the years. But what is unmissable across the different successful products is that they all exist in competitive markets and hold a clear (or as April Dunford would put it, ‘obviously awesome’) positioning. What are some of the unsaid principles you’ve observed when it comes to the perplexing craft of positioning?
it’s always inspiring to hear your words about how to build a business differently - it’s an injection of energy and support we all need right now! I am always impressed with how long you and Chris have been working on Wildbit, and I know from my own experience that there’s always a learning curve in what you are doing.
But here’s my (3 part) question:
What have you learnt over the 20 years that has meant what started off really hard, is now pretty much a breeze?
What always was, and remains always hard to do, and you can never seem to learn how to make it better?
What started off easy and has got increasingly harder over the last 20 years?
Congratulations on your 20th birthday! It’s a wonderful achievement, best wishes for the next 20 years. I really loved your idea of personalized marketing, something we will try to learn from
I love your philosophy of building a business to do what you love to do without worrying about revenue per employee or looking for an exit. I am sure that allows you to build a business that people love to work for. I have the following questions.
How has your philosophy helped you build products that your customers love as well?
I am also curious to see if this approach has helped you launch more products by triggering the entrepreneurial spirit in your employees as well.
I look forward to your thoughts.
Thank you so much for offering to take part in this AMA!
Honestly, after having known about and used Postmark for many many years, I never realised how amazing, how wonderful your ethos is as a business. So great to read.
I am first in line to agree with what you stand for, but I know others have asked me this, so I’d be keen to understand your perspective:
Some of your products are in extremely competitive markets, filled with players that have $millions behind them to scale marketing, sales, product, and customer success. How do you remain relevant and stay competitive when others around you are so well funded?
Thank you, and congratulations on building a wonderful business – the kind of business model that no one should feel like they need to excuse.
Goodness, there were an infinite number of learnings from Conveyor! Where do I even start?
We were building Conveyor with a proven and talented team, along with a profitable business and confidence that we could solve any problem. That led us to push forward by eating the elephant all at once instead of one bite at a time. In hindsight, and going forward, we should have defined what failure looks like ahead of time in addition to what success looks like. Had we done that, I hope we would have seen that we were taking on more than we should have a lot sooner. We shared more of those lessons learned and takeaways on our blog.
Enabling the team to get back on track was the immediate priority once we made the decision to stop working on the product. In Wildbit’s world, where people come first, back on track means enabling the team toward a motivated, happy state. We knew that every person on that team needed to work on something that would make a meaningful impact to customers. Working on something for so long without it reaching customers’ hands can be extremely demoralizing. We wanted to be sure they were able to work on a project that directly impacted customers immediately afterwards, to help them remember what that feels like and reiterate what incredibly talented folks they really are.
To solve for those goals, we opted for some projects that would be finished within 3 months. The Conveyor folks formed new teams and worked on two of our big releases this year: DMARC Digests and People-First Jobs.
I’m not sure that our understanding of risk has changed. What changed was the desire to build something small again, instead of jumping into a complex product. We still love taking calculated risks, as long as they don’t risk the entire business. On the outside it may look like Conveyor was risky because we spent over $3M on it over time. In reality we never risked the house. What we learned was how to notice failures earlier.
I wish it didn’t sound crazy, because caring for people should be a priority above all else. There were many moments where it was less about defending the decision, and more using it as a basis to make better decisions. An example is when our product Beanstalk plateaued in 2012. We felt lost, so we started tweaking and experimenting because it’s what other SaaS companies were doing. We didn’t drive with our purpose of being people-first. We focused instead on what we thought the business needed. When we turned that around and asked ourselves “why”, we realized that we were going about it all wrong.
Instead of thinking about how to grow Beanstalk, we focused on making the people at Wildbit happy and fulfilled. That led to us putting more energy into Postmark, which was a tiny baby at the time. We were excited about growing things, not about competing on features or going upmarket. Beanstalk needed us to growth hack. But the people wanted to enjoy their work. That’s probably one of the most important decisions we’ve ever made. Not only did we end up growing Postmark to significantly surpass Beanstalk, but we did it while building a powerful team that loves what they do.
We absolutely questioned ourselves in the early days about choosing to work 4-day/32-hour weeks. But the beautiful thing about being private is that there’s not a lot of risk in these experiments. Maybe we’re naive, but we’ve been doing this long enough to know that being late to the market with a feature release would never be make or break for a product. It just doesn’t matter that much. By that logic, if the biggest risk of 4-day weeks is shipping late, it’s actually not that big of a risk. When we reflected a year later, we actually shipped more that year than in most previous years. So we knew we were on to something.
There are days even now that I question the 32-hour work week. Mostly because I’m not sure that work, in general, should be so rigid. There are some weeks that I work less than 32 hours, and some weeks where I probably work 40 hours. I am curious about defining a work environment that prioritizes what “enough” is, instead of prioritizing a set number of working hours.
But, if I project a bit on your question, we have never felt that working 4-day weeks would be a competitive disadvantage. And given the growth we’ve seen in our products over the last few years, it feels like an advantage now. (Especially as I welcome a lot of new customers from our biggest competitors daily :).
Hi Rajaraman! This is a wonderful question. I’ll start by saying that the reason Wildbit turned 20 is because we have multiple products. If we only had Beanstalk, it would have plateaued and our options would have really pushed us to sell. Having different products in different markets is a superpower to building a long-term, sustainable business.
I think you see this more in non-tech companies. In tech we call these pivots, and we see them often as company missions shift (I’m thinking of Mailchimp here: They went from email marketing to all marketing for small businesses). But in non-tech it’s not unusual to have multiple product lines to mitigate risks, especially risks we can’t control. Market shifts are just one example.
I agree with you on the importance of really, deeply, understanding your customer and your market. For us that has never felt like a heavy lift because it’s built into how we work. We have a brilliant customer-facing team who are attuned to what customers are saying and feeling. They share all those details with the product teams. We also tend to dogfood and use our own products, so we become our own customers. We also don’t have a traditional sales team. We only do pre-sales conversations to help support potential customers. And the biggest difference on our team is that “sales” lives in Product. Rian, our Head of Product, takes most sales calls. Our customers appreciate that, and it’s a competitive advantage.
With a product agnostic approach, we’re not focused on a single market, persona, or industry. Instead, we look at how the products can support our broader Wildbit goals. Then we give as much autonomy as possible to the folks who are doing the work, and trust them to get it right. As an example, our DMARC Digests product took off pretty quickly and is managed by two folks on our team who share most of the work. Between the two of them, they are also doing marketing, customer research, design, and development to figure out what’s next.
It’s not too different than the four of you starting out. You don’t need a huge team to understand different markets. You need to create space for small teams to have the autonomy and trust to understand what to build next. As I write this, I’m thinking about this HBR article on how Apple is organized for innovation. We do things in a similar way, with teams that can go deep on problems, with the authority to make decisions.
Hi Brendan Revenue per employee is a metric we’ve thought about in the past, too. We also do profit-sharing and run open-book with the team. I realize that revenue per employee is a metric designed to counter the VC model of burn and spending more than you make. As a private business we care deeply about profitability, because we have to. Raising funds isn’t an option for us. But lately I’ve been questioning if this metric is truly in support of being people-first.
In my mind a business is simply a tool used to improve the lives of human beings. The owners, the employees, the customers, and the community. Revenue per employee leans very heavily on prioritizing owners, at the expense of the team or your customers. To maximize revenue per employee you really want to focus on optimizing efficiencies. This leads to decisions like hiring fewer support folks (and then customers suffer). Or when you hire fewer engineers and their on-call schedule is brutal because there aren’t enough people to balance the load.
I’ve been thinking a lot about how we can use our business as a tool to maximize positive impact. I’m a big fan of founders paying themselves. Chris and I have always prioritized financial stability as the company grew. We never wanted to be martyrs or find ourselves in a vulnerable position. So I’m not suggesting that as founders you should be putting yourself last.But it is a question of who else are you supporting, other than yourself. If we think of a business as a tool, the most direct impact it can have is by employing more people. Because every person you hire has impact on countless others (their families, their communities, etc). So the question I keep asking myself is, if you run a profitable, people-first business, should you be hoarding cash? Or instead, should you find ways to balance the need for profit while spending those profits in ways that maximize impact.
I sound a bit like a socialist, but I assure you I’m a capitalist (I was born in Russia, so I pinky promise). I just believe in a more ethical way to build these businesses. And in a real way I want to be sure that our business has more impact than just making Chris and I successful.
Hi Ai! Thank you so much for the kind words. We’re so happy to have you as a People-First Jobs company.
Team structure has been fluid over the years. I’ll start with what we’ve been doing recently, and share a bit about where we want to go.
For a long time, we’ve had teams dedicated to working on specific products. Our biggest product, Postmark, has the largest team. We have a product manager, Rian van der Merwe, who works with folks in design, engineering, and QA that only work on Postmark. Our CS team, led by Dana Chaby, is also dedicated to a single product. And there have been marketing folks dedicated just to Postmark.
The Postmark team has a very structured planning and execution process. Because it’s the largest team, it has the most communication overhead. And because it has so many customers, we treat it differently than a brand new product.
The smaller products have much smaller teams, maybe 2-5 people. They keep their process extremely lightweight by doing their own support, product management, and customer development. We allow those teams to stay scrappy because there is less risk and less overhead.
Then we have some teams who support all the products, like finance, infrastructure, and marketing. Those teams either act as advisors to the smaller teams, or take on clearly defined projects that we map out during quarterly planning.
In the entire history of Wildbit, we’ve encouraged folks to move around the company and work on other products. That’s core to what makes us special. But we try to make those changes no more than once a year, so you can really dive deep into the problems we’re solving.
Starting next year we’d like to be less siloed. We don’t want to have Postmark developers, but instead Wildbit developers. We want a Wildbit customer team, not Postmark customer team. In the immediate term not much will change, but over time we want to be able to leverage the expertise of these folks across all products, and to allow our team to keep moving around inside of Wildbit. This will also help us use our economies of scale to start more projects and not get bogged down. If our engineering team is cohesive, we can reuse principles, move faster, and have consistent processes.
Re: how we decide what to work on. Since we are a smaller team that doesn’t work on 10+ features at a time, our process is fairly straightforward. We follow a quarterly planning cycle, and we rarely plan product roadmap that extends beyond that horizon. So we start with defining our Vision & Focus for a quarter at a company level, and then our teams work together to figure out the best product bets we can place to help accomplish those goals.
We take user needs (through constant ongoing research and collaboration with the customer success team), business goals, and technical needs into consideration to decide on the prioritized themes for a quarter.
Importantly, we don’t plan it all out upfront and make commitments we can’t keep. We start with a project plan that frames the problem we want to solve, and that plan evolves as we progress through the quarter — as we learn more from our customers & competitor research, and as we dig into solutions and discover the best path forward.
At the end of a project or feature we make sure we gather feedback from customers, and make time for our teams to adjust and improve as we learn more from them. And then, in most cases, we start the next quarter fresh. Sometimes that results in a continuation of a particular feature, sometimes it’s something new based on a change in Vision & Focus, but we always go back to those principles, and work in collaboration with the team on how to make the product better. To put it another way, we aim for our team (and their extensive knowledge of customers) to be the product visionaries in the company.
Hi Logesh! It’s definitely a practice to find the right balance, but if you let the beast anchor you, I feel strongly that you’ll end up with regrets.
We try to remind ourselves that a business is simply a tool that we, as humans, created to support us. We are in control of it, so it should be serving us. We course correct frequently by asking ourselves why we’re making certain decisions. The best example is Conveyor. What ultimately led to shutting it down was how it was making the team feel, not the financial implications on the business.
But I think, honestly, the best way to make sure the beast isn’t in control is to make sure you’ve given yourself guardrails. We have strong values and principles that protect us from falling off the cliff. We make sure our way of working supports a people-first approach.
But we are also a very high-performing team. Justine, our Head of Marketing, once shared with me that she is working harder here at Wildbit working 4 days a week, vs. 5 days a week elsewhere. What we’ve found is that when you prioritize people-first, those folks have the space, support, and passion to be extremely high-functioning and high-producing. We don’t ask folks to care, they care on their own.
Hi Aditi! What a great question, it really made me think.
When I’ve talked about our lack of marketing over the years, I feel it’s because we have always been so product focused. But the way you describe it makes me realize we care more about marketing than we make it seem For Chris and I, building a product has always required us to understand its position in the market. Who are we building this for? How will they use it? Why are they choosing us or switching to us?
Our best way to understand our product positioning has been in speaking to our customers, and in hanging out where our customers hang out. We’ve frequently read threads in Hacker News or StackOverflow to hear about how others talk about us. And talk about our competitors. We haven’t always gotten it right, though.
I’m particularly thinking about Postmark in the early days. We built it when there weren’t any email providers focused on transactional. We were sending our own transactional emails for Beanstalk and had no visibility into their delivery. So when we built Postmark, our tagline was “Because you’re blind” referring to the lack of visibility for most app developers into how their emails were being delivered.
A few years later we were having dinner with some other founders and someone mentioned that Postmark gives them confidence that their email is going to get to the inbox quickly. It turns out, when a transactional email (like a password receipt) gets delayed, an app can lose a customer. Or that customer may email support, increasing costs for no reason. We repositioned ourselves pretty dramatically after that. We created a term called Time to Inbox. We started measuring our TTI and the TTI of our competitors. And we started messaging broadly that our promise was to save you the heartache of late-arriving emails.
This transformed Postmark’s trajectory. We hear our customers using our own words ALL.THE.TIME. It’s incredible.
I think the biggest thing I’ve learned is to focus on what’s important. In the beginning we would frequently run towards something without really understanding why. From product features, to hiring for certain positions, or ways to market the app. Today, I can’t imagine starting anything without first really honing in on why we’re doing it. What this means is that making decisions, especially big ones, is much easier now. We start with why, and as we discuss and think, the right answer presents itself much faster than before.
Building teams will always be hard, because you’re dealing with humans, and humans are beautiful, messy, and worth the effort. At every stage along the way, the needs of the team have evolved. And being people-first means that we don’t just fire everyone and hire new people that fit the current needs. We take the time to figure out how we all fit into this thing together. People are the most important part of Wildbit, and will always be the biggest challenge.
What was easy in the early days was making decisions. We were a small team, and we could just decide something and run with it immediately. Frequently, these decisions weren’t well-thought-out. We were just responding to our gut instincts. Sometimes it flopped. Oftentimes these decisions would turn out great.
Today, our decisions carry more weight. We have a bigger team, we have lots of customers, and more to risk. So we try to make sure the decisions Chris and I need to make are less frequent, but have impact.
We talk about this a lot amongst the team. How does being people-first impact our customers? Our customers are wonderful, and they really love us. How did that happen?
Business gurus tell us that taking care of your team means they will take care of your customers better. And this is true. But what that means in practice is our team cares very deeply about our customers, advocates for them, and empathizes with them. Because at Wildbit they have the space and the permission to care. A practical example of this is how we’ve always had rules around how we deploy new features. It was never, ever, acceptable to have our own customers test our products. Everything goes through QA. We will take longer to fix edge cases before releasing, always.
We also have a Customer Support team that fights like hell for each customer. They have the power to hold back a release if they feel strongly it will impact a customer poorly. They know our customers so well that they often act as their advocate when it comes to product development and feature prioritization.
Yes, absolutely. We attribute being people-first to our ability to launch many products—we call this “product agnostic”. We often refer to the team’s entrepreneurial spirit, but I think it’s less about being a starter, and more about having the space and permission to be creative, take risks, and speak up. The small DMARC Digests team of Matt West and Ilya Sabanin, with help from Jeremy Polley, made most decisions on their own. From how much to charge, to what goes on the marketing pages, to what features to build. We, as founders, just provide support and feedback from a 30,000 foot view. But we trust them to make the best decisions they know to make. And since they’re closer to the work, we know in most cases they’ll make a better decision than we would. What we bring to the table is a place to feel safe in making mistakes, a stable salary, and decades of experience. But otherwise, it’s on them to make it work!
Hi James! Thank you for the wonderful words, and for being a Postmark customer!
We always seem to land in the same markets as these 800lb gorillas. What settles us, and keeps us focused, is a clear understanding of what is enough for us. We don’t want to be a funded, fast growth company that IPOs one day. So we focus instead on building a business that can financially sustain ourselves, our team, and all of our experiments.
With Postmark in particular, what really worked for us is playing the slow game. We always held true to our values and principles, from how to build product all the way to how to treat people. We love doing things that don’t scale. For instance, our support team is absolutely second to none. They dive deep into all kinds of obscure issues. We’ve maintained our reputation amongst our early adopters as the “place you go when you really care about your email”. As a small team with smaller expenses, our targets have never been as aggressive as our competitors, so we could play it slower. And in the end, even if our competitors out-market us, we’re second in line once they (inevitably) disappoint folks. We’ve been fortunate that 2020 was a great year for us, and a clear signal that the slow, intentional game really worked. You’ve heard other founders, like Brendan and Nick, state similar points of view in their AMAs. It’s all about brand.
What makes this type of growth special is, as founders, we still control and own the whole business. We could have sped things up by taking on VC, which would have added a ton of risk to our personal success, and lost control to try to chase those bigger gorillas. But waiting a few years to reach our bigger goals was totally worth it, both financially and personally in how we enjoy our work and whom we get to work with.
Thank you so much for doing this AMA with us and for answering every question in such depth. Super grateful!
I’m in absolute awe of the clarity of thought behind the several stances you have taken over the years, whether that’s introspective hindsight or ever-present strategy. And completely loved this: “I sound a bit like a socialist, but I assure you I’m a capitalist (I was born in Russia, so I pinky promise). I just believe in a more ethical way to build these businesses. And in a real way I want to be sure that our business has more impact than just making Chris and I successful.”
There is, undoubtedly, a treasure trove of insights and actionable tools in here, but what I, personally, find incredibly inspiring about this AMA is this very personal definition that you’ve rendered to what a business is and can possibly be. Reminds me of this one time Derek Sivers talked about how the world is unnecessarily ceremonious and all of us can and should define things for ourselves.
Thank you, again, for joining us today and being so generous with your time and insights. Hope to host you soon again!
Thanks for sharing this and other insightful nuggets, Natalie!
It makes absolute sense. Distance from making meaningful impact for customers can be acutely demoralizing for teams. Being people-first, then, also means being well aware of what drives people to come to work. And, noticing failures sooner, is, indeed, a superpower by any measure!