Boston Needs More Companies Willing to Swing for the Fences

And Other Lessons in Scaling from HubSpot CEO, Brian Halligan

If you live in Boston, you need no introduction to Brian Halligan, CEO of @HubSpot, who was recently named the #2 CEO in America in USA Today. Where the Red Sox, Bruins and Patriots are our sports teams of choice, HubSpot has become one of our city’s most prized corporate mascots. Brian joined a small group of founders and operators at Pillar HQ to share how he grew HubSpot from the seed of an idea to a public company with thousands of employees around the globe — the 2nd best large company to work for, just behind Google.

Boston Needs More Pillar Companies

Halligan’s all worked up. California is crushing us, he argues, lapping us many times over when it comes to creating big, enduring companies. What we need is more pillar companies to keep graduating students from heading west. Companies that create an environment where emerging leaders can learn on the company’s dime. Companies that throw off financial benefits for the surrounding community. Companies that are a breeding ground for the future founders who will drive the next wave of innovation in our ecosystem. (We couldn’t agree more — it’s the reason we built our firm.)

So what did he and co-founder Dharmesh get so right that enabled them to create a thriving company here in Boston? Halligan admitted that he doesn’t have a silver bullet answer, but attributes much of their success to the fact that he and Dharmesh were swinging for the fences from the day one. They weren’t willing to settle for mediocrity. They wouldn’t sell out early. They were in it for the long haul, and wanted to build a big meaningful company that would stand the test of time. (Pretty sure I once heard Halligan say he “will be buried in orange”.)

“We need more founders in Boston who are willing to swing for the fences.”

— Brian Halligan, CEO, HubSpot (click to tweet)

While San Francisco has a gold rush mentality, Halligan stressed that Bostonians are puritans in contrast. We’re descendants of buckled up pilgrims. We’re conservative folks who are perfectly happy to settle for a double over a home run; if we want to win and create thriving Pillar companies in our region, we’ve got to ditch our penchant for settling for good enough. Ultimately, it’s up to founders to go big, Halligan stressed. Sure, there are plenty of VCs who push companies to sell to early, but the power that comes from setting your sights on building a pillar company rests in founders’ hands.

Talk About How You’ll Solve Co-Founder Conflict Early

Halligan rarely talks about one of the most remarkable aspects of HubSpot’s growth — the health of his relationship with co-founder, Dharmesh Shah. Surely it helped that the two have complementary strengths and were aligned in their big vision thinking along the way, but Halligan also credits open communication as the source of their success. Dharmesh insisted early on that they talk about how they would split equity (not necessarily evenly) and how they would resolve co-founder conflict. When they hit a bump in the road, they ask whether it’s a “lie on the tracks issue” — would it kill one of them if they couldn’t have their way? If so, they follow that person’s lead. And if they’re at a true standstill, Halligan makes the decision. It turns out these occasions are few and far between, but they’ve got clear guidelines when they do occur.

It doesn’t matter how you align on problem-solving, what matters is that you have the conversation and create clear guidelines for how you’ll work through issues together. Address difficult conversations head on — the more black and white, the better.

When Comes to Hiring, Forget Conventional Wisdom

HubSpot has arguably built one of the strongest management teams in town, and perhaps even more impressively, many have come up through the ranks from within. Halligan’s goal is not for people to become experts in a specific role or team, but rather, to become experts in the business. Start by hiring athletes, then surround them with knowledge about the organization and the opportunity you’re after, your common goal. Teach people to think about how all the different pockets of your organization impact the greater whole. When it works, this approach creates a pool of senior leaders who can close their eyes and understand what’s important to every area of the business, easily navigating different functions in the company.

Teach people to think about how all the different pockets of your organization impact the greater whole.

Many of HubSpot’s senior leaders have done just that — moved from PR to people ops, from product to operations, from operations to customer success. The tradeoff is it can be tough for new people to assimilate, people who are accustomed to thinking only about one area of a business. But the tradeoff is worth it.

Never Settle for Good Enough

From Starbucks Coffee CEO, Howard Schulz, to actress Natalie Portman, plenty of successful people fear that they can’t possibly be qualified for the job at hand, and Halligan’s no exception. When he’s is onstage speaking in front of thousands of HubSpot customers and inbound marketing enthusiasts at INBOUND each year, he’s the picture of confidence. But underneath the polished exterior, he admits that he’s still often haunted by feelings of doubt. There’s a positive spin though — from insecurity grows a continuous quest for self-improvement. Halligan has a great CEO coach, but some of the most valuable feedback fueling his personal development comes from his own team. Every senior leader at HubSpot undergoes an annual 360 review, receiving ~30 pages of feedback from ~20 employees across the company. While Halligan jokes that it can take days to recover from the deep introspection, the review is a critical tool for helping him understand what he’s good at that he should lean into, and where his biggest gaps are as a leader. Sure, feedback can sometimes be a hard pill to swallow, but an openness to understanding how others perceive and are impacted by your actions is essential to personal and professional growth.

Find Your People

Beyond the natural insecurities it can stir up, leading a company as CEO can be a lonely job; while co-founders can be important sounding boards and a source of ongoing support, no one else in the business carries the same weight on their shoulders. Recognizing the importance of building a community of peers, Halligan joined a CEO group in HubSpot’s early days. While it was a challenge to find a group where everyone was growing at the same pace and encountering similar challenges, the ability to connect with people he could relate to alone was a game-changer. The group included Colin Angle, CEO of iRobot, and Russ Wilcox, CEO of E Ink at the time and now a Partner at Pillar — two guys Halligan describes as “pretty weird and totally brilliant.” Both were a little quirky, and both were scaling impressive companies. He saw aspects of himself in them, and thought, if they can do it, so can I. Russ and Colin helped him see that there’s no singular model for successful leadership. So get off CEO island and go find your people.

For a room full of founders listening to Halligan from companies like Soofa, Rekener, Catalant, LBRY and Kuebix who aspiring to build Boston’s generation of pillar companies, one thing was clear — it doesn’t happen overnight. Building a pillar company starts with an unrelenting ambition to create something big and meaningful, a continuous quest for improvement and a refusal to settle for less than the best.

(You made it this far––don’t forget to clap…)