Inside the HubSpot Fellows program: building judgment for the AI era

At most companies, the reward for being an exceptional individual contributor (IC) is that you are eventually asked to stop doing the work you love. You trade writing clean code, architecting systems, or closing deals for calendar tetris, performance reviews, and headcount approvals.

At HubSpot, we have spent over a decade pushing back against this corporate default. We believe "up" is not the only way to grow a career. We design our roles so that scope and organizational impact—not the size of your headcount or span of control—are what drive real growth.

"What I’m proud of here is that we actually invest in that belief—putting the same level of seriousness into developing our ICs as we do our people leaders," says Claire Meenehan, Director of Learning & Talent Development.

To back this up, we run the HubSpot Fellows program: a three-day mini-MBA built specifically for our highest-impact and highest-potential ICs. In the era of generative AI, this decade-old investment has become our ultimate competitive advantage.

Practicing the skills AI cannot replicate

As AI tools like Breeze automate execution-heavy work, the skills that remain essential are uniquely human: judgment, strategic reasoning, and knowing what questions to ask.

"We delivered the Fellows program to practice the exact skills AI cannot replace: judgment, decision-making, communication, influence, and strategic thinking," Claire explains.

To build these skills, we partner with Harvard Business School faculty to teach their case method. We also enforce a strict rule: close your laptops.

Nathanael Yellis, Post-Sale Solutions Architect at HubSpot, was initially hesitant.

"I walked in wondering what we’d accomplish that couldn't have been a Zoom call," Nathanael says. "But the case method requires fast-moving, in-person conversation. You can’t multi-task or fake your answers. There is way more information present in a physical space, moving quicker than any virtual presentation."

Navigating the messiness of imperfect information

The Harvard Business School case method does not offer comfortable conclusions. It drops 45 highly ambitious peers into a room, hands them messy datasets, and cold-calls them to defend their strategies.

It is designed for constructive friction. During a session on the legacy software giant Siebel, Nathanael’s customer-success instincts led him straight into a trap.

"My tendency was to only consider focusing on the existing needs of the current customer base," he says. "It was an inside-out strategy. But the critical trends were external: subscription models and the cloud. My instincts were precisely wrong."

Because the room was packed with ICs from across the business, the correction was immediate.

"The product and engineering folks read the case exactly right," Nathanael notes. "They called out what I said, pushed back, and led me to see that today's software landscape demands a relentless outside-in strategy."

For Tom Lucy, a Technical Lead in our Customer Agent product group, the cases meant trading engineering certainty for strategic ambiguity.

"In engineering, you often work with deterministic systems," Tom explains. "You find a bug, implement a fix, and deploy. But at Fellows, we faced complex business scenarios where every option carried a painful tradeoff. The cold calls forced us to make high-stakes decisions under pressure with highly imperfect data. It reinforced that as a leader, you cannot wait for perfect information to act."

Learning to influence without a formal title

Perhaps the hardest transition for an IC is learning to influence without formal authority. Working with author Liz Wiseman, the cohort examined "Multipliers"—leaders who amplify their team’s capabilities—versus accidental "Diminishers".

"Leading without formal authority is our daily challenge," Tom says. "Learning to create space for others' best thinking, rather than overwhelming them with my own ideas, changed how I think about supporting my team."

Sarah Israel, Senior Account Executive at HubSpot, came away with a similar lesson.

"Exceptional leadership is not defined by title or tenure," Sarah says. "It is defined by the willingness to learn, the humility to embrace different perspectives, and the ability to inspire others."

Over three intense days, Sarah and her peers identified on four core takeaways:

• Courage over certainty: Great decisions are rarely made with perfect information. Effective leaders have the courage to act, learn, and adapt.
• Human connection: As AI continues to transform the industry, critical thinking, empathy, and genuine human connection remain our greatest competitive advantages.
• Living the culture: A strong culture is reflected in every interaction with our customers, colleagues, and communities.
• Partnership over pitching: In sales, customers want trusted partners who understand their deepest operational challenges, not just a product.

Bringing the outside-in perspective back to our teams

The real test of the program is what happens when our ICs return to their day-to-day work.

Since returning, Tom has used his new cross-functional connections to improve the software his team designs.

"I spent hours chatting with peers in Sales and Customer Success who talk to our users daily," Tom says. "Hearing where customers experience friction with our customer agent gave me invaluable insights that I am already building back into our technical roadmap."

Meanwhile, Nathanael has restructured his weekly manager alignments.

"Rather than starting our weekly one-on-ones with micro-level technical details, I try to structure the agenda around our organization’s macro priorities first," Nathanael says. "This opens up opportunities to contribute to larger, high-impact projects."

At HubSpot, we will continue to invest in our ICs with the same seriousness and craft we bring to people managers. In an industry reshaped by AI, human judgment, empathy, and the courage to make bold decisions remain our greatest advantages.

Are you an ambitious individual contributor looking for a company that takes your craft seriously? Explore our open roles and join us in helping millions of organizations grow better.