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Since I sent that message, Jaryd and I have become what I would call 'good mates. This week, as Jaryd pivots his time, energy and cerebral horsepower to another passion—mental health—I will take over How They Grow and roll it into Open Source CEO.

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INTERVIEW 🎙️

Des Traynor, Co-Founder & Chief Strategy Officer at Intercom

Des Traynor is the Co-Founder and Chief Strategy Officer of Intercom, the AI customer service company trusted by thousands of internet businesses. Since co-founding the company in 2011, he has played a central role in shaping its product strategy, leading the R&D organization, and helping grow Intercom into one of the most recognizable names in SaaS. Prior to Intercom, he co-founded Exceptional (acquired by Rackspace) and ran the design agency Contrast.

Known for his clarity of thought and product intuition, Traynor is also a respected voice in the tech world, frequently sharing insights on product-market fit, startup scaling, and customer experience. He’s spoken at events like Web Summit and SaaStr, and actively invests in early-stage startups including Notion and Manna.

What was the most difficult part of going from zero to one?

The hardest part early on was that it wasn’t obvious what the shape of the product should be; or even how common the problem really was. If you're working in a well-defined category, like note-taking, it’s easy to understand the boundaries and user expectations. But what we were building didn’t fit into an existing mold. Startups understood it immediately. They loved that they could use Intercom to talk to their customers and hear back from them. But when I spoke to more experienced people in the industry, they’d use jargon like ‘behavioral targeting’ or ‘engagement engine,’ or say we were an ‘escalations platform.’ None of that resonated with me. It all felt like buzzwords.

The real challenge was that this idea of connecting internet businesses to their customers had no clear boundaries. Should it include email? Sure. Then people wanted reports, attribution, link tracking, integrations with tools like ZoomInfo, and lead nurturing. Suddenly, we were building something that looked a lot like Marketo.

Similarly, when we built a customer data platform, people wanted segments—trial users, new users, premium users.

But then came graphs, event filters, and analytics on behavior. It was hard to draw the line on how much to build without becoming too broad and shallow.

So, the most difficult part was knowing when to stop, deciding which good ideas to pursue and which ones to let go, even if they seemed like natural extensions of what we’d already built.

Tell me about your day-to-day at Intercom?

I work from our office about 95% of the time, unless I’m on the road. Most of my focus is on Fin, our AI agent for customer service. Each day starts with a stand-up meeting for the Fin leadership team, where we go over current customer issues, roadmap items, staffing, resourcing, and any key sales deals we need to be aware of or help push forward.

A big part of my day is reviewing Fin product work—new features, improvements, and iterations. Every 12 to 16 weeks, we run an event called Built for You. We had one about three weeks ago actually where we announced voice, a new Insights product, and also a replacement for CSAT we are calling the CX Score, and there’s always another one coming up.

Our next is in May. A lot of my time is spent figuring out what we’ll be shipping and announcing at those events. The AI space moves so fast that we need to keep pace and meet the market where it is.

Outside of product work, as a founder, board member, and executive, I have a lot of other responsibilities; welcoming new hires, prepping for board meetings, and handling various high-level tasks across the business.

Who are your direct reports?

I have three: our chief product officer, Paul Adams; our CTO, Darragh Curran; and our chief engineer and co-founder, Ciaran Lee. When I’m not deeply involved in the details of Fin, I work closely with Paul and Derek to help manage our 500-person R&D team.

How do you think about leadership?

I see my role as a leader as providing energy, direction, and clarity. While I ultimately report to our CEO, who sets the company’s overall strategy and culture, I do my best, especially being based in Dublin while much of our leadership is in San Francisco, to bring momentum, positivity, and progress to the teams I work with.

Energy can take different forms. Sometimes it’s optimism; "How awesome would it be if we pulled this off?" Other times it’s pressure; "If we don’t get this done soon, we’re in trouble." People draw energy from both, and I try to apply the right kind at the right time. Injecting energy is a huge part of my job, and I push myself to do it every day.

Clarity is the other big part. People do their best work when they understand and believe in what we’re doing. If a task seems unclear or disconnected from a real goal, it’s hard to expect full effort. But if the objective is obvious and important, most people will go all in. I try to lead by consistently reinforcing that clarity and context.

And finally, fun and celebration matter too. You have to actually enjoy the journey—enjoy who you work with and celebrate even the small wins. For example, when we launched Fin as a self-serve product, our first customer signed up for just $49 a month. It might seem small, but we celebrated it. Because one day, that same flow might bring in a million-dollar customer. And it all starts with that first small spark.

What amount of time you spend applying pressure energy vs positive energy?

It really depends on the situation. It’s not something I’d quantify as a fixed percentage. When something’s broken, you can’t just cheerlead your way through it. You have to be direct: "Hey, we’re in a tough spot, and we need to fix this fast." If a new competitor emerges and poses a threat, that’s not a moment for positivity—it’s a moment for urgency and focus.

But there are plenty of times when positivity is the right tool. In the early days of AI, for example, we were genuinely excited. We saw what was possible, and we were among the first to launch an AI agent for customer service. That was a big moment, and we took the time to celebrate it. Sometimes, though, one moment can carry both kinds of energy. If GPT-5 dropped tomorrow with new possibilities, it would be incredibly exciting, but also pressure-filled. We'd need to move fast, be first, and do it well.

I often joke with the team, “Tell me what motivates you more; fear or excitement?” Because some people respond better to pressure, others to vision. It’s about knowing your team and using the right energy at the right moment.

What is your North Star?

With Fin, our North Star is enabling every internet business to deliver as many customer resolutions as possible, instantly and accurately. That’s what we care about most: are we actually solving people’s problems?

The way we calculate our resolution number is fairly straightforward. It’s a product of three things: how many customers we have, how frequently they use Fin, and how well Fin actually works. Multiply those together and you get the total number of customer resolutions Fin delivers. That metric is a major driver of what we do. We’re constantly trying to win more customers and help them automate more of their customer service in a way that genuinely works.

Is there a broader macro set of goals or themes for the organization?

At the organizational level, we have six objectives for the year, and each one has a directly responsible owner. For example, I’m responsible for building the best possible version of Fin. That objective breaks down into maybe seven or eight different workstreams, each focused on a specific feature or unlock. Whether that’s for a new market, a new integration, or something else.

That’s how everything ladders up. Each objective is broken into initiatives, and every initiative has someone’s name next to it, along with a clearly defined scope and timeline—something like, “It’s going to be this good, and it’ll be live on this date.”

We strongly believe in directly responsible owners and singular, threaded leadership so that there’s always clarity around who’s accountable for what.

The high-level goals are set annually, and then at the departmental level—like in my org—we break those down into quarterly objectives. So at the start of the year, we might say, “Let’s build the best, most differentiated version of Fin in the market.” That can include objectives like addressing sales blockers, launching multi-platform integrations—making Fin work with Zendesk or Salesforce—or enabling voice support or action completion.

Each of those becomes its own workstream, and that’s where the roadmapping comes in. For any given workstream, we ask: how far can we push this in a 12-week period? We might say, “By the end of this quarter, we want it in beta and being used by at least three customers.” That’s the level of planning and structure we operate with.

Who was your ICP, and how has that changed over time?

Today, Fin works for customers of all shapes and sizes. The main requirement is that you do customer support on the internet. Beyond that, everything’s pretty flexible; you could be a 10-person startup or a 10,000-person company. You might be using Zendesk, Salesforce, or Intercom. Fin doesn’t really care about the size of your company. It just needs to be able to resolve conversations well and at scale.

But that wasn’t always the case. When we started, Intercom was best suited for early-stage startups trying to find product–market fit. That was our initial ICP. These were founders and small teams who wanted to stay close to their customers. They wanted to support them, talk to them, launch features inside the product, all of it. And Intercom let them do that.

As we grew, we split the product into different areas—customer support, in-product messaging, engagement—and each of those naturally developed its own more refined ICP. For example, our human support help desk product tends to serve companies with 1,000 to 2,000 people, typically online businesses. We do have customers bigger than that, but once you’re dealing with ‘teams of teams of teams,’ it sometimes requires features we haven’t built yet.

With Fin, though, the game changed. Because of how it works, the size of your company or volume of conversations almost doesn’t matter. You could have 10 million conversations a year, and Fin can handle it. So the ICP has really expanded. From small startups to now encompassing the full range of internet businesses doing customer support at any scale.

What is the overall recruitment strategy at Intercom?

I can really only speak to recruitment within our R&D org where we build, design, and manage the product. At our scale, we hire across a broad spectrum, from interns and fresh graduates all the way up to senior principal engineers, and our in-house AI team, that’s stacked with machine learning PHDs. The employer value proposition is different at each level. For interns or early-career folks, Intercom is a place where you’ll work on real production systems, writing AI code that actually ships. You’re on a live team, doing real work from day one.

At the more senior end, we’re appealing to people who want to join a well-run product organization and work on top-tier AI technology. For example, Fin is one of the more widely deployed AI agents on the market, and it’s generating real revenue, tens of millions. If you want to work on meaningful AI products that are making a real impact, we offer that opportunity.

Overall, our strategy is to make the work itself attractive. Not perks, not surface-level benefits, but the actual substance of the job. We want people who are genuinely excited about the space they’re working in. Whether it’s UI, core engineering, AI, or large-scale systems—whatever their craft is, we want them to be passionate about it.

That’s always been our approach to hiring: attract talent by making the work itself worth doing.

What are the stages of the recruitment process for a senior or leadership hire?

For senior or leadership hires, the first call could be with a recruiter, but depending on the level, it might also be with me, our CEO Eoghan, or another C-Level exec. That initial conversation is usually pretty light. It’s about learning more about the candidate, clearing up anything ambiguous, and making sure there’s enough alignment to move forward into a full interview process.

After that, we put together a panel of two to three senior people on our side. Each person will focus on a specific area based on the role’s needs and any open questions about the candidate. For example, if we’re hiring for a role that needs strong leadership, high resilience, and hiring capability, we’ll tailor the interviews to test for those traits.

Assuming that goes well, we often include a workshop stage. That’s where the candidate is asked to write a short strategy document—maybe one or two pages—on something relevant, like how they’d grow mindshare for an AI agent. The idea is to see how they think through a problem when they’ve had time to sit with it. They’ll then present that back to the same group they interviewed with, and we’ll have a back-and-forth discussion. We’re not just looking at the content, but also how they collaborate; can they take feedback, merge ideas, challenge bad ones?

If that all goes well, we move into the closing stage. That includes reference checks. Not just the usual ‘tell me who to call’ kind, but deeper, unscripted ones. We’ll try to find someone who worked with them at a relevant company during a specific time period to get a more honest and independent perspective. That’s how we get a real sense of what it’s like to work with them.

How do you get the best out of yourself personally and professionally?

Over time, I’ve become really aware of what gives me energy and what drains it. I think about a lot of life through the lens of energy management—how do I stay in a place where I’m not feeling burned out or depleted? Everyone’s different. Some people get energy from public speaking; others find it exhausting. Some thrive in workshops and whiteboard sessions, others prefer solo deep work. For me, I’ve tried to keep track of what fills me up and what takes it away.

I want to be at Intercom. I want to do this job. I want Intercom to succeed. So it’s not about finding motivation, it’s about making sure I have the energy to deliver.

And when something does drain me—whether it’s a type of task, a conversation, or a dynamic—I look at it in two ways. Option one is to try to eliminate or delegate it. Talk to my manager, or a teammate, and figure out a way to move it off my plate. But often, that’s not possible. So option two is to get good at it. Sometimes that means learning how to have tough conversations, or how to do focused desk research, or how to stand up and give hard feedback in a room.

And a lot of times, the resistance you feel isn’t about the task itself; it’s about something deeper. Maybe you had a bad experience with a manager in the past. Maybe you’re still carrying that, and it’s making a normal part of leadership feel harder than it should. In those cases, the work is personal. It might involve journaling, therapy, or just figuring out why a seemingly small thing hits you so hard.

At the end of the day, leadership isn’t just about good news and pay raises. It’s about doing hard things you might not be naturally wired to do. I’m always wary of people who try to dodge the hard parts of leadership. The truth is, sometimes it just hurts. And you still have to do it anyway.

And that’s it! You can also can also follow Des on LinkedIn, or learn more about Intercom on their website.

BRAIN FOOD 🧠 

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TOOLS WE USE 🛠️

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