Outercom: A new class of founders answering the Intercom buzz

11 Feb 2022

Gradguide founder Mark Hughes, TrueNorth co-founder Jin Stedge and Unflow co-founder David Newell. Image: Intercom/Gradguide/TrueNorth/Unflow

Over 10 years, Intercom has not only scaled its own business but the Irish-founded start-up has nurtured a large cohort of product-driven entrepreneurs.

“Everyone had a side project.” That’s what Gradguide founder Mark Hughes found while working at Intercom. “It was always encouraged to have your own thing.”

Today, Hughes is founder and CEO at Gradguide, a career guidance and graduate recruitment platform he dreamed up when he himself was freshly graduated and considering his career path. Knowing then that he wanted to one day found his company, he set out to join an Irish tech start-up that he believed would give him a roadmap for that journey.

Hughes was happy to find that the entrepreneurial mindset was encouraged as early as the interview stage at Intercom. In fact, he thinks it’s what helped him land a job with the sales team. “They didn’t really care about my CV,” he said. “It was more like, what side projects are you working on?”

‘There’s no red tape or bureaucracy. I took that from my days at Intercom’

Intercom, a San Francisco start-up from four Irish founders, started out more than a decade ago. Since then, its software to assist businesses in communicating with customers online has seen it grow to become a tech unicorn. That is, a start-up worth more than $1bn.

This was the very goal set out by Des Traynor, Eoghan McCabe, Ciaran Lee and David Barrett in the early years of Intercom. The company was founded in 2011 from the proceeds of the sale of Exceptional, a bug tracking tool they had built in Ireland.

Though established in California, Intercom still has deep roots in Ireland and a large operation in Dublin. At the close of last year, the company reported more than $200m in annual recurring revenue and revealed plans to nearly double its workforce here by the end of 2022.

The company is well-known not just as a homegrown success but for its engagement with and support for the local start-up sector. And in its 10 years, Intercom itself has become a breeding ground for new start-ups. A large, growing community of ex-employees turned entrepreneurs convene in a Slack channel called ‘Outercom’ to share ideas, what they’re working on, and tips on securing investment.

Hughes had his own funding news to share with the group last year when Terry Clune’s investment group took a majority equity investment in Gradguide for €2m. Like Hughes, Clune had the idea for his first venture, Taxback.com, as a graduate. He got wind of Gradguide when one of his group’s many fintech companies, Immedis, became a pilot user of the platform.

The Clune connection drove Hughes to monetise Gradguide and take it full time, and he immediately went back to previous employers Chargify and Intercom to land his first customers.

But that’s not the only link between Gradguide and Intercom. Hughes has brought with him a ‘strength in speed’ approach to building a start-up that he learned at his former company.

“It’s how smaller companies compete against bigger companies,” he said. “[Speed is] what they fear in a start-up. They can move really quickly. They can iterate. They can launch new features and functionality really, really quickly.” To enable swift decision-making, “there’s no red tape or bureaucracy, it’s a flat org structure,” Hughes explained. “I took that from my days at Intercom.”

Hughes has also copied Intercom’s weekly ‘Show and Tell’ showcases for Gradguide’s own version with a notably Irish twist. “It’s called Reeling in the Week,” he said.

‘For the first time, I had tons of female role models’

Jin Stedge also fondly remembers Intercom’s Show and Tell Fridays. “It was happy hour time for the Dublin office and breakfast time for the San Francisco office,” she recalled. “It’s really hard to work with people who are eight hours apart from you and I think those small things really made a big difference.”

Stedge is the co-founder of TrueNorth, a start-up launched in February 2020 that has already raised more than $60m in funding. Before starting her founder’s journey, she spent 18 months as business operations manager at Intercom’s US headquarters. She was attracted to the job by the opportunity to work in Dublin as well as San Francisco. “They had the most amazing breakfasts,” she said of the Irish office.

It was at Intercom that Stedge, an aerospace engineering graduate, discovered her interest in working in tech. Then, after a stint working on self-driving tech at Scotty Labs, she decided to hit the road with TrueNorth, a company bringing the great digital transformation to truckers. “When Covid hit, all the warehouses shut down and all of the trucking company workers had to start working from home. So they actually had to start using digital things,” she said. “It really accelerated adoption.”

As CEO of her own company, Stedge has also carried through a leadership style she learned at Intercom. “From the very beginning, we’ve made it clear that all of our teammates really care about one another and get to know one another.”

This is inspired by her first project at Intercom for which she worked directly with Traynor. She noticed that Traynor, the co-founder of the company who visited the San Francisco office about once a month, made a point of knowing every person that worked there.

“Intercom was probably 300, maybe 400 employees [at the time],” said Stedge, recalling a time Traynor felt compelled to start a conversation with a person in the building he realised that he hadn’t met yet. “The fact that he took that kind of care to know every single employee across multiple continents was pretty remarkable.”

In her short time at Intercom, Stedge also worked alongside CTO Lee and “a lot of different awesome women”.

“In almost every role, I’d had at least one female role model. But for the first time, at Intercom, I had tons of them,” she said.

Intercom is now woman-led, with Karen Peacock installed as CEO in 2020 when co-founder McCabe stepped back following a decade in charge. This move came a year after McCabe apologised for “poor judgement” in his behaviour towards women employees in the company’s earlier years. An independent review initiated by the Intercom board after harassment allegations came to light in 2019 found that these matters were “handled appropriately”.

McCabe, now chair of Intercom, said he had pegged Peacock for the top job even as she was hired as COO in 2017. Like Traynor, she is known to make an effort to connect with employees. “Every lunch, no matter how busy she was – which was really busy – she would sit down and talk to someone,” Stedge said.

Stedge is now creating an equitable, thriving environment for women in tech at her own company, and is proud that half of TrueNorth’s 50 employees are women.

Headshot of Des Traynor in a dark shirt, pictured against a dark grey background.

Des Traynor, co-founder, Intercom. Image: Conor McCabe Photography

Traynor has led strategy at Intercom for 10 years. His commitment to openness as a leader stems from a drive to share the learning that leads to better decision-making, which is something he has carried through from his background as a lecturer.

“If you want somebody to make the same decision you’d make, they need access to the same decisions and the same decision logic that you have,” he said, citing a key tenet of transparency in leadership.

“We strive for this sense of authority, accountability and autonomy,” Traynor elaborated. “In order to be held accountable for something, you have to have the freedom to do what you want, and you have to have the authority to command orders to do the things that you think you should do. If you don’t let that happen, what often happens is people start being like, ‘Well it wasn’t my decision to do this.’ And that’s the exact wrong mindset for a start-up.”

‘In order to be held accountable for something, you have to have the freedom to do what you want’

Though he hates to describe the organisation of Intercom as a ‘start-up within a start-up’ model, he is an advocate of giving product teams start-up-like experiences.

“They do behave and work a lot like a small company, working hard on building something for their customers. And they do think of ‘their’ customers, and they do run betas and talk to them,” said Traynor. “All of that tends to be the actual skillset you need to build your own product.”

And so it comes as no surprise to Traynor that Intercom employees have left to found start-ups such as Gradguide, TrueNorth, Unflow, Vidu, Equals and more. But he’s also confident that this is a good way to retain staff.

“From what I can see in all of the data, people generally like working in that sort of environment,” he said. “It’s quite engaging for them day to day, and they miss that culture if they leave and end up somewhere where it doesn’t work like that. And oftentimes they’ll come back.”

One such ‘boomerang’ employee was David Newell, who said: “There was a joke that I’d gotten three P45s and somehow still worked there.”

Looking for an internship placement during his final year of college, Newell was excited to find a San Francisco tech start-up actually building product in Ireland. He enjoyed the placement at Intercom so much he set about working his way back after graduation.

The timing couldn’t have been better as Intercom had just raised funding and was on a hiring spree. He reached out to his old intern manager on a Thursday and had a contract signed by Saturday.

‘It was very much a product-driven company’

It was a dream job for a young engineer who had been happily building things that no one was using. “In my first week I built a feature that made the message sending clearer to customers and, all of a sudden, millions of people were using it or seeing it,” he recalled.

“There’s certainly not many companies whose product is adored as much as Intercom’s,” Newell added. “It was very much a product-driven company – I think everyone knows that – but almost engineering driven and led as well.”

Newell also benefitted from skill-sharing with his workmates and ‘Intertours’ – spending weeks working with different teams. He and Hughes, who joined Intercom around the same time, would trade engineering and sales advice.

Perhaps the most crucial connection he made at Intercom was Patrick Finlay, with whom he went on to found Quorum and then Unflow. “We sat two desks away from each other and I think the only reason we didn’t sit beside each other was because we probably would have got no work done.”

Newell, Finlay and fellow engineer Romy Lynch founded a start-up from the kernel of an idea back in the summer of 2019. They were accepted into the Y Combinator accelerator and, like many to pass through its programme, pivoted under its guidance, emerging with Unflow, a no-code tool for building mobile app experiences.

Having first-hand experience of the Intercom story helped Newell as a young founder. “It’s that cheesy phrase: You can’t be what you can’t see. I’ve seen a version of it,” he said.

The “humble beginnings” of Intercom are shared often and openly. They’ve even put out a book on it. “Once you hear those stories from the people they happened to, you understand that everything starts small,” said Newell. And at Intercom, “start small” is a mantra. “I think of all the lessons from my time there, that’s probably one of the biggest,” Newell affirmed.

The freedom to build at Intercom was also bit like dabbling in the start-up world in safe mode. “Had I not been given that autonomy and flexibility to do that within the safeguards of the Intercom product and system, I don’t think I would ever have the confidence to do it now either,” said Newell.

Some other iconic Irish founders also inspired a confident approach in securing new clients. Dubbed ‘the Collison install’, Newell heard talk at YC of how John and Patrick Collison, the Irish brothers who founded Stripe, would approach small businesses directly and ask if they had payments in their app. If the answer was no, the response was to get a laptop open and install Stripe within 30 minutes.

“I tend to do that kind of thing with smaller apps,” said Newell. “And if they don’t want to ship it to the App Store, that’s absolutely fine. I just want to know if our SDK will install on their product.”

‘Be the culture that you want the culture to be’

When Newell joined the Outercom Slack channel, there were about six people in it. Now it numbers more than 100. “I think the scariest thing about running a start-up is that you’re out on your own,” he said. “I have the Intercom support network, which I wouldn’t have had had I not worked there.”

Some might be tempted to draw comparisons between this cabal of founders with their roots in one key start-up and the infamous PayPal mafia. This group of former PayPal employees and founders includes billionaires Peter Thiel and Elon Musk as well as LinkedIn co-founder Reid Hoffman, 500 Startups founder Dave McClure and YouTube founders Steve Chen, Chad Hurley and Jawed Karim.

There is a distinct sense, however, that Outercom represents a different breed of founder. And Traynor, too, notes the generational difference.

“When the Pay Pal folks got up and running in all their new start-ups, step one for building a company back then was that you better go raise some money ASAP,” he noted. This was the early noughties before cloud services and AWS dramatically cut the capital required to start a tech business by providing access to public servers.

“There was this massive cost to start,” said Traynor. “Because of that, the accessibility of who could start would be trickier.”

Now, he sees companies such as Gradguide, Unflow and TrueNorth building a product first, validating it with users, and then seeking investment. “That model probably wouldn’t have been possible in the earlier days.”

When we spoke at the end of 2021, Traynor was very optimistic that this new product-led style of growth was leading to a landmark year for Irish start-ups. “I believe there’ll be two or three Irish unicorns in the next while, I’m very confident in that,” he said – and he was dead right. 2022 is still young and we’ve already seen Wayflyer and Flipdish join the unicorn club.

Traynor forecast five to seven more Irish unicorns by the end of this year, and he himself is invested in many start-ups with great potential including &Open, Tines, Tito and Orreco. “If I list them all we’ll be here all night,” he joked.

As an active investor and mentor, Traynor is generous when it comes to sharing his experience. He previously spoke frankly and honestly about his founder’s journey at Inspirefest 2019, diluting the myth of the tech playboy with a story of hard graft, spreadsheets and countless emails.

Though still a start-up, Intercom has now reached such a scale that Traynor may not know every single staff member, vendor and service worker by name, but he does his best to stay connected. “Be the culture that you want the culture to be,” is his maxim.

Which begs the chicken or egg question: is it that Intercom’s culture inspires entrepreneurs or that it hires them?

I’ll leave that answer to Newell, who said: “I think more so that a lot of people were taught a methodology and a way of thinking, and given a grounding and a foundation to grow professionally, that has led them to the place where they can do their own things.”

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Elaine Burke is the host of For Tech’s Sake, a co-production from Silicon Republic and The HeadStuff Podcast Network. She was previously the editor of Silicon Republic.