Building a Generational Software Company – Insights from HubSpot’s CRO Mark Roberge

April 12, 2016

Mark Roberge has been part of the HubSpot team since the beginning and currently serves as an instructor for HubSpot Academy’s sales training course and certification that’s been taken by more than 15,000 salespeople. He and HubSpot co-founder Dharmesh Shah were classmates in the MIT MBA program, working side-by-side on their respective business ideas, getting together once in awhile for Chinese food and shop talk. After graduation, Shah hired Roberge as a consultant, and a year or so later Shah’s co-founder and CEO, Brian Halligan, invited Roberge to serve as a member of HubSpot’s founding executive team. Since then, Roberge has served as SVP of Global Sales, SVP of Global Sales and Services and currently serves as HubSpot’s Chief Revenue Officer of its Sales Division. Through it all, Mark has played a pivotal role in the building and scaling of HubSpot’s sales organization.

Over the past ten years, HubSpot has grown under the guidance of Shah, Halligan and the rest of the leadership team to become a major force in the inbound marketing space. Today, more than 16,000 companies in 90 countries use the HubSpot platform to attract, engage and delight customers with personalized experiences. Though company headcount has grown exponentially since the early days, the focus on strong culture and quality relationships has never wavered. The team has done an exemplary job of harnessing a diverse set of strong personalities to create a highly effective and innovative team.

Starting with Respect

Right from the outset, respect played a big role. “To be honest, I didn’t foresee a nine-year career at HubSpot,” admits Roberge, thinking back to Shah’s initial invitation to join the team. “Initially, I was just excited to get a paycheck and stabilize things at home. I never would have said yes if I didn’t have such great respect for Dharmesh and Brian, their vision and their passion.”

That sense of respect was reciprocated, and also mutual between the two founders. Early on, as the company was beginning to gain some momentum, Shah and Halligan disagreed about the best way to continue growing their company. When Roberge joined full-time, the customer count quickly expanded to more than 100 over a two-month period. At this point, as the developer, Shah wanted to pull back on the acquisition push so his team could focus on refining and perfecting the product. Looking at things from the CEO perspective, Halligan was eager to start hiring more salespeople and ramping up that operation.

Caught in the middle, Roberge was impressed with the way the co-founders worked through the conflict, “Even though Dharmesh was the original founder of the idea, he recognized that he didn’t want to be an operator and brought in Brian to really run the company,” says Roberge. “And, unlike a lot of pure founders out there, he and Brian were truly co-founders together. Even in times of disagreement, Dharmesh was true about letting Brian run the company and ceded the decision to him.”

Walking in the Other Person’s Shoes

Getting a handle on roles and responsibilities was another key to the team’s success. “We had a lot of learning to go through together there,” Roberge says. “Brian was a first-time CEO. I was a first-time VP of Sales. We scraped our knees through that process, and it all worked out.” If Roberge had to give another first-time executive team advice today, it would be to appreciate the responsibilities and perspective of the different leadership roles.

“Typically CEOs are really stressed about fundraising at that early stage,” Roberge explains. “They’re worried about living up to investor expectations so they’re thinking ahead to what they want the investor deck to look like in 12 or 18 months when they need to raise the next round.” On the sales side of the equation, the focus is very different. “We’re sitting here with four people, and on the spreadsheet it looks beautiful to expand the team to twenty, increase productivity by 10 or 20% and find new demand gen scenarios,” says Roberge. “But there’s a lot of black magic in this plan, and if I don’t make it happen, I’m fired.”

Closing the gap between these two perspectives requires open, transparent communication in which everyone not only understands the other parties’ priorities, but also has some empathy for the situation. For instance, the VP of Sales should not only perceive the role the sales team plays in the context of the company vision, but also feel the same sense of urgency that the CEO feels about hitting goals in order to ensure the next round of funding.

Likewise, the CEO, whose job is to worry about investors and funding, needs to step back and look at things from the viewpoint of the sales team. “There’s got to be a similar empathy from the CEO to the VP of Sales,” Roberge says. “The CEO should think about how to better support sales, maybe by budgeting for sales engineers, a sales manager/trainer or a recruiter.”

The bottom line is that team leaders need to have what Roberge calls “proactive empathy” in times of crisis instead of resorting to finger pointing. “If things go sideways,” he says, “ You need to help the person dig into the diagnoses and sort through a potential solution as opposed to just saying, ‘We didn’t hit the number. It must be your fault.’”

Aligning Around What’s Best for the Company

Ultimately, the goal is to have an organization full of people who have respectful and supportive relationships with each other, but who also each have a strong relationship to the company. As an example, when asked about how much he feels he has to “protect” his sales team from certain elements within the company, Roberge says that he didn’t consider shielding his team as head of sales. His job, he explains, was to put the best interests of the company first, his team second and himself last. By maintaining the insights he gained from looking at things from the perspective of other leadership roles, Roberge makes himself – and by extension his team – more strategically and tactically effective

“When you’re in those executive strategic discussions, you need to take your sales leadership hat off and put on your executive team, board member, investor, stockholder hat,” Roberge says. “You need to always look at these issues from the perspective of what’s best for the company.” And then you go back to your respective teams and do the hard work that has to be done. “We’re not here to maximize our next quarter’s paycheck,” he emphasizes. “We’re here to build a company that survives on.”

Image by Rachel Worthman


<strong>CeCe Bazar</strong> is an Associate on OpenView's investment team. She was previously a Sales Strategist also at OpenView.