Between Sales and Product: Building Out Self-Serve and Customer Experience at Notion & Dropbox

 was graduating from the University of Southern California in the midst of the recession — not the optimal time to be job hunting. She took a chance and sent a cold email to Marc Benioff (a fellow Trojan). Within 10 minutes, the founder responded and introduced a recruiter to Taylor, who ended up landing a role as a corporate sales rep.

That email kicked off what would prove to be an impressive career in tech. Taylor left Salesforce to join Dropbox in 2012, starting in support and moving into channel and sales development. She spent the better part of the decade figuring out the company’s famous self-serve funnel and refining the product feedback loop, ultimately leading their SMB revenue and scaled sales operation. Fast forward to August 2020, when Taylor joined 

 as their new Head of Customer Experience, a role that combines products, sales and support to run what she calls the “front door experience” for customers (more on that later).

Here on The Review, we’re struck by how Taylor has strung together a fascinating set of experiences, from the classic top-down sales motion she saw at Salesforce, to the bottoms-up adoption and 

 that propelled Dropbox and Notion. She’s built a career that, as she puts it, has been focused on finding the balance between sales and product — a skill that’s in high demand these days. 

As founders are increasingly leaning into 

 and self-serve strategies, there are plenty of potholes to derail their progress. For both sales-driven companies that are intrigued by self-serve and 

bottoms-up businesses wrestling with when to layer on sales

, Taylor makes for the perfect guide. In this exclusive interview, she unpacks common traps and tensions, comparing and contrasting her experiences at Dropbox and Notion to offer up sound advice on finding the middle ground between sales and self-serve. She also delves into strategies for thinking through pricing and packaging, approaching product prioritization, and building a better customer experience.

From how Notion’s incredibly tight product feedback loop works, to the pricing experiments Dropbox learned most from in the early days, Taylor shares a treasure trove of helpful anecdotes and actionable tactics that will have founders and go-to-market leaders taking notes (in Notion we hope).

SHIFTING FROM SALES-LED TO PRODUCT-LED: FINDING THE MIDDLE GROUND BETWEEN ENTERPRISE AND SELF-SERVE

Taylor was in for a world of change when she made the leap from Salesforce to Dropbox. “When you’re building a company, you're trying to figure out who is that target market? Where is the company the best fit? At Salesforce, that was very clear when I came in. I learned a lot about targeting specific segments and what that flow should be like, especially when the average deal size is extremely high,” she says. 

“In transitioning to Dropbox where it was more product-led, that model flips on its head. You have to look for opportunities for self-serve to lead and sales to follow. The question is more about 

 and how product can drive the sales funnel. Ultimately, I've ended up nestling myself in between product and sales. At both Dropbox and now Notion, our perspective was that 

we don't want to leave customers behind. 

Finding that middle ground was super pivotal.”

Instead of forcing a sale, focus on getting to the right place — and testing to make sure you’ve arrived.

But the process of unearthing that middle ground took time. “The team that I ran at Dropbox was called inbound sales. At first, it was part of the sales org, but we eventually realized that wasn't a good place for it. When people came to the website, they had interests across different categories. Maybe that was buying, maybe it was support needs, or wanting to know about partnerships — my team was actually more of a routing function,” says Taylor. 

So we moved into the marketing org, took quotas away and started to make it more of a value-driven effort to answer questions and get people to the place they need to be

. And that often may have been over to the sales org, but it could have pushed them into the self-serve flow or over to support. Once we discovered that interacting with customers should be more of a value-driven conversation, that was when things just started to click.” 

The team was starting to get customers to the right place instead of trying to force a sale.

 that things were clicking. “We actually started testing this at Dropbox. Once we got a little bit more intelligent with how this team was operating in between go-to-market and product, we ran experiments where we held out a set of control customers and compared them with a variant group to test if these conversations were driving value,” Taylor says. “

 and less on revenue, and then see what happened compared to the control. And we saw a considerable lift in revenue

. Reps were motivated off of having value conversations and answering the quick slam dunk questions that customers had.” 

There was value in it for sales folks as well. “Customers end up in self-serve and they may have questions and aren’t quite at the sales line. Now sales was saying, ‘Thanks for getting this customer the answer, now they're in a trial,’ or ‘Now they're ready for a much larger discussion because they understand a basic need,’” says Taylor.

It's easy to put up barriers on the site or make it difficult for customers to get in touch. We did the opposite at Dropbox, believing that value would drive revenue and LTV. And we actually tested that to be true.

Build a land-and-expand flywheel and grow alongside your customers.

The handoff between self-serve and sales became a well-practiced alley-oop. “At Dropbox, we found that the goal of self-serve was landing teams and getting them to love the product. And then sales was about taking those teams and helping them understand the value of the product up market — as opposed to the traditional model where you've got sales cold calling and trying to source these wall-to-wall deals,” says Taylor.  

“Completely honestly, looking back at Dropbox, that cold sale just did not work. And we tried it quite a few times in enterprise. Instead, have upmarket sellers focus on what they do best, which is selling wall-to-wall deployments and getting people using and loving the product at larger companies. And then self-serve is focused on creating product-qualified leads for that type of motion.”

If you let the product lead and sales follow, this natural flywheel starts spinning and it starts to click for customers.

This thinking translates well to Taylor’s role at Notion today. “We want to lead with getting people into the product, understanding it, and then building that adoption and groundswell for sales to go and sell into,” she says. “We’ve seen that many of these enterprises started as smaller deployments and as they've grown, these needs for our more advanced features kick in. And that's when we start to have that sales conversation. It usually happens with growth and maturity. And the relationship we’ve built along the way is what enables us to have that conversation.”

 as an example, says Taylor. “They started as part of our startup program, with about 20 seats. And now they’re using and loving Notion as they've grown and scaled considerably. That’s an ideal use case of a company that's growing significantly and finding leverage with Notion — brought in by a self-serve program and as they grow, our sales team is there to help them find additional value,” she says.

But of course, it’s not always so seamless. Tensions bubble up to the surface when the respective swim lanes of sales and self-serve are less than clear. Here, Taylor highlights potential pitfalls:

Getting caught up in a competitive streak

. “It's really hard for an enterprise team paired with a self-serve motion, because your product is always, in theory, cannibalizing itself. When you can sign up very easily, that's a really hard model to pursue because sales is ultimately fighting the product itself and product adoption.” Instead of trying to validate itself against self-serve, the sales team should adopt a different mindset, says Taylor. “Instead of constant competition between enterprise and product, what we should be doing is making it really clear for customers that if you're of this certain size and these are your needs, then this is the product for you. Instead of competition, it should be about creating a healthier funnel.” There’s potential bristling on the self-serve side as well, but a mission-focused mindset also comes in handy. At Dropbox, Taylor’s team was charged with figuring out where customers were falling out of the funnel and serving up conversation at those points to both help the customer and learn about the friction points in order to drive that feedback back into the product. Counterintuitively, 

Taylor’s goal for her “self-serve assist” team

 was to make self-serve so much better that she’d ultimately have less revenue and a smaller team over time.

“What really worked at Dropbox is that self-serve became a land motion for companies of all sizes, and then sales was focused upmarket, for companies of 250 or more.” But company size isn’t always a clean dividing line, however, Taylor cautions. “It's easy to say a company size is a great way to divide up customers, but that doesn't always work. The buying process for a five- to 10-person team at Nike might actually mirror a buying process for a SMB,” says Taylor. “So what you really want to think about is some kind of line between team size and company size — and making it as easy as possible for someone to get into the product.”

“As you layer on self-serve, if that side starts to take off, you might back off of the enterprise feature development. It’s tempting to shift away and start to build more on self-serve,” says Taylor. “But at Notion, we're taking an opposite approach, which is: Self-service taking off. That's great. Even though it’s going well, if enterprise is where we want to be, then we need to continue building out functionality that supports it. And ultimately it will go down market and benefit all users,” she says. “It's that dedication factor — when one starts to win, do you shift resources? Trade-offs in those moments are difficult and it's the dedication piece that often can shift in a world where you don't have unlimited resources and you have to make a decision.”

Self-serve isn’t about competing with sales, it’s about creating a healthier funnel. There are tradeoffs and tensions along the way, but you need to stay the course.

PRICING, PACKAGING AND ONBOARDING: LESSONS FROM EXPERIMENTS AND UNITING USE CASES

Pairing self-serve with enterprise sales can cause a wrinkle over on the pricing page, however. That’s because there’s a menu of options to choose from — charging for incremental features, per seat, based on usage — and competing incentives. “As we are looking at pricing and packaging at Notion and which type of model we want to pursue, the licensed model always makes sense for us in an enterprise setting, just because as you think about distribution for users who are coming on and off, it's the easiest way to manage,” says Taylor. 

“But there's a component for self-serve and SMBs where usage is actually a major driver, so thinking about paywalls around usage or with the free product tend to be the easiest way to drive value quickly.”

To illustrate the impact this has on customers, Taylor serves up an example from her Dropbox days. “Dropbox views their website as a product. The goal is conversion — we wanted people to start as many trials as possible, and the pricing page was one of the biggest conversion opportunities,” she says. “My team saw that there was heavy drop-off for users after around 30 seconds on the page. And so as an experiment, we started to put chat just below the 30-second mark, with the goal of catching users right before they dropped off to figure out why they were stuck and ultimately serve that feedback back to the product team.”

Here’s what they discovered: “The users coming to the site had no idea which plan they were on. So when they're looking at which plan to pick, they don't even know where they're starting from. I mean think of Netflix — what plan am I on? I don't know what it's actually called,” she says. “And so it was a very simple product fix — if the user is logged in, illuminate which plan they currently have to help give them the idea of where to go.”

For Taylor, this was both a key learning and a proof point in the value of self-serve. “Afterwards, we could quickly spin down that chat on the pricing page. A bunch of users were able to convert because of this change and that flywheel that my team continually built with product,” says Taylor.

In these pricing and packaging moments where all of us are so focused internally on what we're trying to differentiate and build for each tier, we lose sight of the fact that the page can drive a lot of confusion and that our users don't even know what tier they're actually in.

Focus on activation, but don’t lose sight of the user’s context

“At Dropbox, we used true-up models, where you pay for a minimal amount of seats, and then look back at the end of the quarter to see how many people are actually using the product. Those models tend to work in the early days, but become a bit difficult to continue when counting revenue. But it starts to give you an early indication of how adoption is going,” says Taylor. 

“With a company like Notion where there's a lot of viral adoption upfront that doesn't tend to be necessarily the biggest issue — users are already using and loving the product. It’s more about bringing multiple self-serve teams together, all under one umbrella,” she says. “At Notion, our sales team is looking to bring in all of that usage and have that conversation around why it’s important for Notion to be that central hub for a company, versus a collaboration tool on a single team. The value is really when you've got different departments in different groups using Notion together.”

But illustrating that is important — which is why onboarding and activation is so critical. “In trials, we're trying to prompt users to take different product actions and create a more active workspace. The key here is the 

One key learning from Dropbox was to keep metrics as simple as possible here

. We used to do health scoring across 15 different dimensions, and it was really hard to move the needle on any health score when you have so many different factors.”

In addition to keeping things simple, Taylor learned the importance of not losing sight of your user’s context. “We did a lot of retention experimentation with self-serve at Dropbox. We were trying to rewind back to that moment where you had to be engaged — as in, if you weren't engaged past X time, you just weren't going to renew,” she says. “We did a bunch of campaigns to reverse through the life cycle and ultimately found out that if you weren't active in the onboarding period, it was unlikely you would reactivate.”

But this is where your product builder bias can creep. “

We had specific situations at Dropbox where users were not technically active by our definition, but when we engaged with them, we actually found that it was an indispensable tool and they couldn't live without it. 

And it was because they were storing all their information in there, they knew it was safe and they trusted the product, even though they didn't access it regularly,” says Taylor. 

“It was a good reminder to continue to test your user base, talk to people and engage with a variety of different segments and really understand what they value. So often you sit in your own environment and that's really not what your users are experiencing,” she says. “We’re sitting here in San Francisco on our Macbook laptops, but that’s not how most of our users experience the product. I try to remind myself of this every day at Notion. Most of our users aren’t in the U.S. and so it's important for us to put ourselves in the shoes of our users and continue to check what's important to them on a regular basis.”

Unite use cases through product “aha” moments and the power of community

Of course, this journey of activating small teams, getting adopted by larger teams and then expanding into company-wide deployment brings the challenges of juggling multiple personas and use cases to the forefront. “We used the 

 at Dropbox. It's important to understand the different jobs that someone is paying you to perform for them. And with different departments, each one is going to have a different need,” says Taylor. 

“In terms of product strategy, it's a real challenge to decide whether to go deep in one specific area or go wide over specific use cases, and in a world where you obviously don't have unlimited resources, you have to pick one specific direction and pull out the common themes. 

For self-serve, it’s about trying to create the ability for users to identify or find common ground with personas

. That was ultimately what we tried to do with Dropbox,” she says. “At Notion, we're trying to make it really easy to unlock people's use case early on through templates.”

Taylor points to a fresh example. “Right now we're building out a 

. We've had it moving now for about a year and a half, and we're trying to make it easier for startups to unlock the value of Notion in their context. So for example, you might have pitch decks that you're trying to put together, or you're getting an early product roadmap in place. When you start your workspace, how could those things just exist there for you so you can dive in and start using them in real time?” she says. 

“For the sales team, for example, that might mean having a 

 that was pre-built. And so through templates, we're trying to get into these use cases so that it doesn't feel as nebulous or as much of a white space. 

In the sales process, you obviously try to identify use cases upfront. But in self-serve you've got to use the product to actually make your way there. It’s about unlocking that quick “aha moment,” but then bringing you along to uncover new ways to use the product.

In addition to templates, Notion is making use of its 

 to help users find value in the product. “One of the biggest things I've seen at Notion that's different is 

. We have an amazing network of folks who preach how to use Notion and do all of this viral marketing for us,” says Taylor. “And these people are running their own business as a consultant, teaching how Notion works on YouTube and holding meetups and seminars in their own communities. They're actually creating templates and selling them themselves. And out of that we spun up this 

Unlocking this professional-level service community outside of Notion has enabled the team to tackle product onboarding at scale, says Taylor. “It’s really powerful. 

I’m actually even using some of our amazing ambassadors and consultants to help with training and onboarding for new Notion employees

 — there are some very passionate and expert-level folks in our community who we can leverage more, even internally.”

Our community keeps us tapped into the real work and tangible value people are finding in the product — as opposed to just what’s happening in our heads. 

PRODUCT PRIORITIZATION: BALANCING NEEDS AND BUILDING A BETTER FEEDBACK LOOP

Layering sales on a bottoms-up self-serve motion is a highwire product balancing act — developing the features that enable product-led growth and deliver on what customers want, while investing resources into the enterprise features that will enable more upmarket wall-to-wall opportunities. Here, Taylor gives us a window into how Notion and Dropbox approach this conundrum.

Commit to a course, instead of thrashing back and forth.

If Taylor has one piece of advice, it’s to commit.

In the early days, Dropbox didn’t have the conviction to commit to enterprise she says, and in her view, that ended up being a mistake. “When I started at Dropbox, we basically released a team product that had centralized billing and we only did it because some users said, ‘Hey, we need to be able to pay for all these accounts on one credit card.’ And then slowly but surely we added some engineers and resources to it,” she says. “But it was a bit thrashy because we pivoted every couple of years. We would go hard on enterprise and then back off and move to building photos. Then we’d shift toward enterprise and then back off again and move toward consumer docs.” Without decisiveness on the company strategy front, bringing on an enterprise sales team but failing to point the product in that direction can cause sales to flounder.

At Notion, however, it’s a different story. “Through the interview process and since I’ve joined it’s been very clear: Notion is going to be an enterprise company. We want to build for larger companies. And so there's a balance of building features that our users need and rely on all the way to where we want to be in the future,” she says.

In a world where there's limited resources and issues you can’t resolve in six months or a year, you have to commit to a direction for the long haul.

Customer feedback is critical to help drive that product direction. The centerpiece of Notion’s efforts here? Their elaborate feedback tagging system. “Every conversation we have with a customer or prospect — unstructured emails, chats and call scripts — is manually tagged across sales and my team with our system of 700 tags.” While that might seem overwhelming, Taylor says even that’s a whittled-down list. “The real art of it is that these tags are pretty specific. So they might be specific to not just databases generally, but database properties or relational database issues,” she says.

“What’s more is that those tags actually port into our product roadmap in Notion, informing both our overall product strategy as well as the building process. As engineers are working on specific features, they're seeing real-life tallies of relevant tags on things that they're currently building for.”

Making sure that the product feedback loop is continually moving is one of the most valuable things that we've done since the early days. 

But how do they take all that bottoms-up feedback and square it with the top-down product vision? “It's basically one giant prioritization exercise. The product roadmap is driven off of our user feedback in tags, mixed with the strategy of where we actually want to go, plus this art component of 

“For example, this year we sat down and looked at the most frequently requested features, taking all the tags and looking at what was most important to users. And since we’re trying to build a product that's focused on teams and moving into the enterprise, we’re also considering the features that can help build on that use case. And then it's sitting down and looking at what's realistic to build, planning in half years.”

CUSTOMER EXPERIENCE: GETTING USERS TO OPEN THE FRONT DOOR

Soliciting and meticulously categorizing all of this product feedback connects back to the mission of Taylor’s customer experience team. Every company wants to be 

, but she’s found a way to truly operationalize the concept of caring about the customer. “In my role, I’m thinking about how we build out the ‘front door experience’ at Notion,” she says.

Here’s what she means: “My team spans across product, sales and support, and we’re trying to drive value for Notion users across all of the experiences they have with us. 

If you believe that putting customers first and having conversations with them ultimately drives LTV and increases the actual dollar value of that customer, then interacting with them should be a no-brainer

,” says Taylor. “We view the customer interaction as not a cost center, but as a requirement, as an area of investment, because that feedback enables us to continue to drive that product intuition internally.” 

The concept I like to talk to the team about is customers coming into our living room, sitting down and having a conversation with us — how do we make it feel that easy to talk with us? How do we make users feel at home when they open that front door and engage with us?

What does that look like in practice? “That means putting in more ways to get in touch and hear more from people, not less. How do we actually just help customers when they need us, making it very easy to contact us, either in the product or on the website? It means not just sending a simple link to a help center page to close out the conversation,” says Taylor. 

Much of this, of course, runs counter to traditional customer service thinking around reducing average handle time. “The customer service goal is not to get them to stop talking to us — it's actually to pivot the conversation around and learn more,” she says.

Instead of trying to avoid customer conversations, how do you make it easier for them to get in touch and find the information that they need? How can you try 

To find more signal in these conversations and surface deeper motivations behind feature requests, Taylor relies on these questions:

•Tell me why that feature is important to you.

•Tell me more about your business and what you're hoping to accomplish

•Tell me more about your workflow that would cause you to ask this question.

Instead of influencing their thinking or referencing existing features, these questions help hone in on their deeper needs — the things they’re really trying to do. “The goal is to help identify more of where Notion could drive impact currently or how we could change the product to drive more impact in the future. It's this feedback loop and it helps users understand that what they're talking to us about is actually critical to the company,” she says. “Again, it goes back to this concept of living room hospitality — we want them to feel like they're part of the process with us. They should leave every conversation feeling like they made an impact.”

This ethos can be traced back to Notion’s early days DNA. “We were very, very focused on engaging with every single user on Twitter. We would get back to every single person, and we still do that today. Customer obsession has to come from the top down, and Ivan has always been very focused on reading direct feedback every day from our users to drive what's in his head and where he thinks Notion is going.”

Yes, helping one user will help them individually find value and understand the product. But they're part of larger communities — and if you believe that writing the best story with that user then allows them to go tell someone else about the product, that’s how you unlock that viral growth.

This article is a lightly-edited summary of Kate Taylor's appearance on our new podcast, "In Depth." If you haven't listened to our show yet, 

Car driving over a bridge and body of water

Self-Serve Lessons From Dropbox & Notion

Kate Taylor spent 8 years at Dropbox leading their SMB revenue and scaled sales operation) and is now the Head of Customer Experience at Notion. Here, she shares actionable tactics on getting product-led growth, self-serve and customer service right — from how to build a tighter product feedback loop, to lessons from pricing and packaging experiments.

Notion's Head of Customer Experience shares tactical lessons on closing the gap between product and sales.

Between Sales and Product: Building Out Self-Serve at Notion & Dropbox

Unpacking 5 of Atlassian’s Most Unconventional Company-Building Moves

There are plenty of young, flashy startups that seem to be overnight successes, bursting onto the scene, grabbing headlines and growing at a break-neck pace — 

 isn’t one of those stories. The company has been humming along for 18 years, quietly shifting the ground underneath traditional tech companies.

 was in the center of the action. He joined Atlassian back in 2008, and under his long tenure as president, the company grew from $20 million in AAR to about $2 billion today. Now, as a partner at 

, he’s got plenty of stories to tell about the unconventional moves that positioned Atlassian to become a global leader, with a suite of software collaboration tools like Jira, Confluence and Trello.

Most have heard about Atlassian’s storied lack of a traditional sales force. But in our conversation with Simons, we found that this wasn’t the only outlier in the company’s story. If you turn over any stone on their path to scale, you’ll likely uncover something that bucks a trend. Whether it’s the company’s genesis in Australia — far outside of Silicon Valley’s center of gravity — or the unusual dual-CEO leadership structure, or a second product launch in just their second year — it’s a growth story that doesn’t get nearly enough of the spotlight it deserves.

“It was really rare for us to just do something that works somewhere else. 

We always began culturally with the question around, ‘Why is it done that way?

’ I want to understand it first and maybe there’s room for not just incremental innovation, but real invention that can make a big difference for us,” says Simons.

Constant willingness to reinvent the wheel takes a shit ton of courage and energy. It’s way easier to just rip the page out of the playbook and follow the script.

 and sidestep conventional wisdom, and Simons is game to get deep in the weeds to unpack each of these atypical moves. In this exclusive interview, he gets incredibly tactical about each leg of Atlassian’s three-pronged stool: the self-service funnel, a global network of channel partners, and enterprise upselling. He also dives into why the company relied on product-led growth before anyone coined the phrase, his theory on why HipChat lost to Slack, and the flywheels that fuel and reinforce the company’s up-and-to-the-right growth. There’s plenty of spot-on advice for go-to-market and revenue leaders, but also lessons for any company-builder on architecting a product and culture that’s rooted in first-principles thinking.

UNCONVENTIONAL MOVE #1: BUILD ON THE BACKBONE OF PRODUCT-LED GROWTH.

In any conversation with Atlassian insiders, you’ll likely hear one word over and over again: flywheel. “We gravitated to that metaphor early on because a flywheel is a big, heavy device that takes lots of energy to spin. You typically can’t get it to accelerate fast because it takes so much to push it. But once you get it going, it’s going to move at a consistent pace, and there’s small things you can add to move it a bit faster,” says Simons. “Conversely, it’s hard to stop a flywheel — you can’t just grab onto it and bring it to a halt. That feeds into what we’ve always tried to architect for, which is the durability of the business as a whole.”

For Atlassian, the core ingredient in the flywheel is product-led growth, an ethos that predates Simons. “Even before I got there, the company’s earliest mission is characterized as building remarkable products. They were really intentional with the word ‘remarkable’ because they thought, ‘We want to build a product that compels people to remark upon it,’” he says. “Atlassian believed that we’d built a product that was easy to use and that people loved, and that was going to add to the megaphone of getting the word out about who we are and what we do.”

A lot of companies worry about how to sell a product before they build a product that can sell itself.

But a lovable product alone isn’t enough to crack into a crowded landscape. Atlassian deployed a trio of tactics to smooth out some of the potholes customers often step into:

“The product and the business model are really married together, and that’s what we got right,” says Simons.

, and architected everything around that self-service model. “First you have to build a great product that people can discover on their own, begin to use on their own, onboard effectively on their own. If you can’t do those things, it’s not going to work,” he says.

So rather than pointing prospects to a traditional “contact us” form and a pitch from a salesperson, Atlassian prioritized an intuitive onboarding process that didn’t need a ton of explaining. In the present day, bottoms-up SaaS gets plenty of attention, but back in 2002 when launching Jira, Atlassian got its fair share of sideways looks. “We were early adopters of AdWords, and wanted to meet the customers at the point where they were looking for something to solve a problem. That was something that IBM or our free and open source competitors weren’t really doing,” he says.

Beyond grabbing eyeballs, there were several other bumps the company needed to smooth along a prospect’s path. “We wanted to have the product guide the customer through in the same way that a human being would if they’re sitting right alongside the customer. That meant making it easy for them to transact online and buy the product. We needed a price point that didn’t require a lot of explaining or convincing,” says Simons.

Now, Atlassian has a tiered pricing structure which includes a free version, a standard version, a premium version, and an enterprise version. But that wasn’t the case in the earliest days. “At the time, we were so focused on reducing the cognitive load on the customer that was coming to us. And if you have four different versions at four different price points, that’s very difficult to help the customer wade through,” he says. Instead, Atlassian landed on a single price point for the product, at just above free. But that meant reducing the overhead on distribution to stay out of the red.

Scaling up with a different kind of sales force.

Rather than an army of salespeople, the company invested in what it called product advocates. “We would say to every customer, ‘Let us know how we can help.’ Our product advocates were absolutely focused on the success of the customer and they were there to remove whatever potholes the customer might step into. They’d answer a question on product capability, or competitive alternatives, or pricing, but with a great answer, they would then send the customer back into the self-service path,” he says.

The one-to-many commerce engine and emphasis on self-service meant the company’s human capital was much more cost-effective, leaving plenty of green space for scaling up.

Once you go down the track of scaling with manpower, it’s very difficult to say, “Woah, we could actually fix all these things in the product, and then we wouldn’t need as many people.” Once your train is set in motion, it’s difficult to jump to a different set of tracks.

“Atlassian now has probably close to 5,000 employees and, relative to most enterprise software companies of that size, it has a fraction of the number of quota carriers because of that flywheel approach,” says Simons.

The company thought of this self-service funnel as a product in itself, and constantly tinkered with opportunities to optimize. “If somebody went through an evaluation of the product and said, ‘No, I’m not going to buy it,’ we would spend a bunch of time understanding what the headaches were that convinced you to go somewhere else, and look for patterns that we could smooth out,” he says.

The business model ends up becoming the business. It’s equally important as the market you’re going after and the product that you build.

UNCONVENTIONAL MOVE #2: LAUNCH A SECOND PRODUCT INCREDIBLY EARLY AND LEARN WHEN TO LET GO.

, in Atlassian’s second year, which is really unusual — especially when you’ve got a breakout product like Jira that’s growing really nicely. Conventional company-building wisdom would say not to do it — there’s still a ton of work you need to do on the first product, and it will fragment your focus once you start working on a second thing, which could be a death sentence for a young company,” says Simons.

Not only did Confluence become a cornerstone of Atlassian’s product suite, but Simons also spots plenty of less-tangible uspides. “We began to build this muscle around how you think about cross-merchandising, cross-selling, and upselling. 

 and packaging around multiple things? How do you do product planning and prioritization and budgeting and staffing?”

At a really early age at Atlassian we began to wire our brain to think about all of those things that companies need to do as they get bigger.

That’s not to say the decision to add new products is always unanimous. “There’s lots of debate and planning and thinking that goes into the trade-offs. When you’ve got a business that you’re running and there’s lots of things you need to do for existing customers, starting something new does draw away from that. It’s got a zero sum,” he says. “It all begins with listening to the market and listening to the customer, and paying attention internally at the itches that we’ve had to scratch for ourselves, and whether or not we think those are transferable to hundreds of thousands of customers.”

Every time you create something new, it’s going to take away from something that’s already here that also needs more coal in the furnace.

“Turning over all the different products Atlassian has introduced or the acquisitions we’ve done, each one of them involves a different set of debates and agreeing to disagree or disagreeing and committing,” says Simons.

While launching a second product in your company’s relative infancy has its own thicket of traps to avoid, there’s a whole new set of challenges to contend with as the company grows. “It’s harder as you get bigger too, because the product you add actually needs to be bigger. For a company like Atlassian that has individual products that are hundreds of millions of ARR, a new thing that you add has got to grow pretty quickly, and it’s got to have a big market it can grow into,” he says.

The sting of losing to a young upstart: HipChat vs. Slack.

But Atlassian has been on the other side of the table too, and got beat by a competitor with a singular, laser focus. “HipChat was a growing product and used by lots of companies, but at the time the market was still pretty nascent. 

 before the market was ripening to what those technologies could do, and then did everything right.”

“History is painted with some examples like this one where you’ve got Slack just ruthlessly focused on one particular thing and moving forward and moving faster and innovating, while we were trying to do a number of things simultaneously,” says Simons.

Atlassian eventually announced in 2018 that they would divest 

. “It’s hard for companies to admit that something’s not going the way that you want it to and open up a really honest conversation with both the market and its customers. 

It’s easier for companies to just keep chugging along, add a couple features, and mostly just ignore it

One of Atlassian’s values is “Don’t f*ck the customer.” We felt that not being honest about our feelings that we can’t win the category in the long run with HipChat and give it our full attention was going against those values.

Simons now calls himself a cheerleader for Slack, and is proud that the Atlassian team made the gutsy call. “There’s an opportunity cost to not divesting, and it means less focus on the opportunities where we feel like we’ve got a better shot at winning outright,” he says.

UNCONVENTIONAL MOVE #3: HAND OVER THE REIGNS TO CHANNEL PARTNERS.

When it came to building up their enterprise customer base, once again Atlassian resisted the urge to pull from others’ playbooks. “When Atlassian was really young, we would come across customers in the enterprise and they’d say, ‘I’m comparing you to IBM Rational and IBM is sending in a whole demo team and doing a dog and pony show, I want Atlassian to do the same thing.’ We chose not to invest in that directly,” says Simons. “Instead, we thought it was the perfect opportunity to build a channel partnership ecosystem, because if we wanted to make a push for the enterprise, those big companies were going to need some hand holding.”

 can seem like an intriguing solution to stop up some company gaps. But without clear swim lanes, the relationships can quickly turn sour. “What happens a lot of times is the direct sales motion can begin to cannibalize the opportunity for the channel partner,” he says. Simons walks us through the common traps: “It starts with, ‘Hey, it’d be great to have a company in Korea that represents us in resale.’ But then you get to a certain size, you’ve got your own people there, and they start to focus on the biggest opportunities,” he says. “The channel gets pushed down the value stack, and they go from being able to sell and support the largest companies to the medium ones, and eventually only the small ones. At that point, they’ll probably diversify to find additional products and companies to represent, and their attention is fractured, and then the channel is degraded.”

building out your own internal sales force faces plenty of its own challenges

. “If you think about building an international business, a lot of companies will say, ‘I need my first boots on the ground in Europe.’ But it’s not just boots on the ground, because you don’t just need a salesperson, you have to think about how that person is supported with marketing,” says Simons. “Eventually, there’s going to be tax implications for paying the salaries and how they’re transacting with customers locally. There’s a bunch of other stuff that comes with planting a flag in a particular country, and it can get immensely complicated.”

But the reason channel partnerships are tricky — and rarely executed well — is that giving up control is something most company leaders aren’t particularly fond of. “It’s hard to trust a third party outside of your company with the core part of your business — which is finding, selling, converting and making customers successful,” says Simons. “We had a really symbiotic relationship with the channel because we weren’t competing with them directly.”

It’s easier to hire your own salespeople and you control them and train them. It’s hard to be represented by a third party, and it requires you to do things differently.

But it’s a trade-off Atlassian was willing to make for longer-term growth. “We were focused on where we could get leverage that improves our speed and velocity and efficiency of the business. We didn't have our own sales team that was hunting for the best deals. Whenever there was a really big opportunity, we were motivated to introduce a channel partner of ours to handle the sales engagement,” he says.

It’s now a core part of the company’s marketing flywheel, and created a brand-new ecosystem, with over 400 Atlassian channel partners around the world that employ many thousands of people. “If it was just us, with a team of 100 people in Germany, that approach I believe is dwarfed by the thousands of partners in Germany that get up every day, without a business card from Atlassian, but are in essence working for Atlassian,” says Simons.

UNCONVENTIONAL MOVE #4: DEFER A PLAY FOR ENTERPRISE.

What began as a single product (Jira) with a single price has since evolved into a full product suite and a more traditional tiered pricing structure. But that simple self-service remains core to the Atlassian brand — even with its largest customers. “Still today, most new customers that Atlassian acquires come through a self-service funnel,” says Simons. “Even if you’re a Fortune 10 company, you might start with Atlassian with a team of 10 or 20 or 50 or 100. And in that particular case, you could be spending less than $1000 a month, but as you begin to grow, we’ve got the advantage of having natural network effects in our products built in, because they’re collaboration software. You might start with 10 users of Jira on a team, and as your team adds an 11th or 12th person, we naturally benefit from that expansion.”

Rather than prioritize signing big-ticket contracts with thousands of seats, in the earlier days, Atlassian leaned on lower-lift tactics. “We would focus on, through marketing and product nudges, highlighting the path for a customer to product B, or C or D. If you use Confluence or you use Jira, we want to point you at the other one, and often that’s as simple as a little pop-up or a little tip when you’ve pasted a Google Doc link into a Jira project that says, ‘It looks like you’re connecting content to your Jira project. Did you know there’s an easier way to do that? Click here,’” says Simons. “Every product in Atlassian’s portfolio is effectively a product that a customer could begin with or a product that they could expand to. I can start with Jira and expand to Confluence. I can start with Confluence and expand to Bitbucket. I can start with Bitbucket and expand to Trello.”

With the company’s “land and expand” strategy firmly in place, the company deferred any true enterprise focus, instead prioritizing something decidedly less sexy. “We were effectively rearchitecting our cloud — which serves this massive spectrum of customers from teams of two up to teams of 10,000 or more. We really needed to rebuild that so that it will be the predominant platform for Atlassian for the next 10, 20 years,” says Simons.

If it sounds like an obvious trade-off, it certainly didn’t feel that way to Simons at the time. “When you think back to 2011, 2012, most of the customers in the enterprise segment at that time were using on-prem products. So we could have said, ‘Let’s go after this enterprise opportunity and defer cloud. I think that would have been the wrong choice, but that’s a very strategic choice,” he says.

Atlassian chose to trade off faster short-term growth and opportunity for the long-term durability of the company, which is a trade that we would make every single day.

Eventually, with the long-term cloud strategy in place, the company turned to a renewed focus in enterprise, based on customer feedback. “We had lots of things that large enterprises were asking us to do. As we began to invest in them, we thought that there was a product offering here for these big, big existing customers of ours to upgrade to. Our largest customers, when they had sometimes 10,000 people running on a version of Jira, there were some things they wanted that weren’t in the product,” says Simons.

With a larger roster of enterprise customers, the timing felt right to make a play — and the bottom line reflected that impulse. “In some cases that upgrade could move them from spending hundreds of thousands of dollars a year to potentially millions of dollars a year. At that point, it really made sense for us to be a bit more proactive with those larger customers that we had material growth opportunities with,” he says.

Self-service from the smallest customers to the largest.

The company added its first Enterprise Advocate role in around 2013, and set off on the journey to finding product/market fit. “We had advocates contact those customers and begin to talk to them about the capabilities that we were looking to add and what the price points were. It was effectively a traditional sales job,” says Simons.

After months of conversations and the realization that they did have product/market fit, the company once again doubled-down on self service — even for this new, premium product tailored to the enterprise. “The thing that we did that again gives us leverage, is we said, ‘Great, we've figured out that we've actually got product/market fit at a price point that people are going to pay. Let's put it on the web so people can buy it online if they want to. And then let's incorporate automation work in the product to nudge an admin or nudge a primary sponsor of Jira towards this premium version that they could either add to their bill, or they could upgrade at an annual renewal cycle and do it on their own if they don't want to talk to anybody,” he says.

With the introduction of premium, enterprise products, the company’s original single pricing structure has since evolved to a more traditional tiered system. “Now, if you look at Atlassian today, the pricing structure has gotten more complex. It’s got a pretty common menu of free, slightly above free, standard, and then premium and enterprise,” says Simons.

It may seem counterintuitive to Atlassian’s founding principles, but Simons sees this evolution as only possible because of that unconventional beginning. “Atlassian is more established in its market with its product brand. So the additional 

 is offset by its position in the market and its brand. Customers are probably willing to spend a little bit of time learning about the Atlassian choices because they know who Atlassian is then if it were just a company they’d never heard of before,” he says.

It all goes back to those early days, when Atlassian put a premium on getting into as many companies as possible, not just the companies with the most seats. “It helped us when we were unknown and young and small because it was just so simple — 

 actually worked in our favor, where you just came to the web and it was like, Oh, Jira’s one price. I just need to think about the number of users, I don’t need to think about, ‘Does it include this? Does it get SSO and the security stuff or no, that’s in the enterprise package. Is it worth twice as much for that stuff? There are all these questions that the customer gets bogged down into thinking about and that’s friction,” he says.

Friction can be okay in the right context with the right approach, but in our particular case, we chose not to introduce it. We were just going to make it simple. We're going to go for high velocity volume customer acquisition, and we're going to reserve future opportunity to have those expansion conversations with those customers.

As Atlassian’s footprint grew, the tiers began falling into place. “By the time we decided to consider expanding our product tiers, guess what? They’re already hooked. They’re already deeply committed. They love the product, and it’s used by thousands of users. Now they just want some extra security features and if we want to charge them for it, it’s probably easier,” says Simons.

“I’m not recommending that every company follow this playbook, but I do think the ‘keep it simple’ strategy benefited a lot of other things we were investing around. It really gave us the freedom to establish a system that we were able to build and improve over time,” he says.

UNCONVENTIONAL MOVE #5: PUT A PREMIUM ON FIRST-PRINCIPLES CULTURE.

Perhaps nothing demonstrates Atlassian’s commitment to going about things its own way like the S-1 filing. “The cover photo of our IPO filing document had a picture of one of the Dr. Seuss characters with a quote from him that said, ‘You’ve got to be odd to be number one.’ We wanted to signify that we’re different and unconventional, and those things are virtuous for what we’re trying to accomplish,” says Simons.

In the company’s earliest days, leadership honed in on three main buckets to focus on innovating: business, product and culture. “Those were the biggest places where we invested in first principle thinking and these were the most foundational elements of the business that we’re all building to outlast us. So it really matters that we take our time to think about them and not just rip a page out of the playbook and follow a script,” says Simons.

unconventional approach to performance reviews

 to something as simple as the dreaded quarterly employee survey, leadership was wired to look for levers to try adjusting. “

Not all of the approaches worked, but what’s important is we tried to do things differently. When they work, those differences matter a lot.

 When they didn’t work, you can always just go back to the way that 90% of the companies do performance reviews,” he says. “I’m proud that we weren’t dogmatic about it. We were just super curious and thoughtful about how we can make different things work.”

To put a finer point on it, one example from early on in Atlassian’s journey was the team decided to refuse any pricing or terms and conditions negotiations. “If there was a customer that said, ‘Listen, I need to negotiate my warranty or my indemnity clause or my payment terms,’ 

we basically just said no — and it’s hard to say no to someone that wants to give you money

. But we basically said ‘We’re not paying for people to do that with you because we’re charging you so little for the product. We pass on those savings of not having lawyers or salespeople negotiating your discount and give you cheaper software. If it’s really important for you to negotiate your indemnity clause, probably one of our competitors will do that, but they’re going to charge you 10 times as much.’” Eventually, the company nabbed its first 50,000 customers without a single modified ULA, and was an eight-year-old business before hiring its first lawyer.

I always remind people that there’s no business where you get 100% of the customers. You’re going to lose some for various reasons. We were comfortable early on losing customers that wanted different things than what we were going to offer.

Some company-builders may hear that story and cringe, but Simons is more than happy to keep taking the road less traveled. “There’s an argument that says, ‘Think about the money that you left on the table,’ and that the customers that walked away were probably the big ones,” he says. “But in the long run I think Atlassian was better off when you think about the efficiency and velocity of how the business operates now.”

When we were at $20 million ARR people would look at us and say, “it’s cute that you guys do it that way, but there’s no way you get to $50 million without doing the thing that every company has done before you.” Then the benchmark became $100 million and then $500 million, and finally $1 billion.

This article is a lightly-edited summary of the key takeaways from Jay Simons’s appearance on our new podcast, “In Depth.” If you haven’t listened to our show yet, be sure to check it out

Cover image by Getty Images / Paper Boat Creative.

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