Built Different: Trusted with a blank page

There's a particular kind of overwhelm that comes from having too much permission. Full latitude and a mandate without a map, weighted by the question of what to build and why.

Kaiya Salemy knows that feeling well. She was hired to turn HubSpot's social impact work into a program. To take a loose set of nonprofit relationships and goodwill and build something intentional and connected to the business at scale. She sat with the weight of that for months.

What made it navigable was the culture she walked into — a place where spending five months doing groundwork counts as progress, and where shipping something imperfect comes with real permission to get it wrong first.

The raw materials were already there when she arrived. Nonprofit relationships across HubSpot's major regions. A high-level focus area. Goodwill. But there was no through-line, no program architecture connecting the work back to the business in a deliberate way.

“Part of what was communicated to me was that they wanted a fresh perspective and a fresh look at the programming. I took that to mean I could come at it like a blank page in some ways. Which, of course, was daunting.”

She'd spent eight years at her previous company, a completely different product with a completely different approach to social impact. She needed to learn HubSpot from the inside first.

THE LISTENING TOUR

Of course she had milestones — the same way anyone in a new role does. But the program itself wasn't on a 90-day clock, and nobody expected it to be. She spent five months doing groundwork.

Starting in August, she spent the rest of that year on what she calls a "listening tour," though it was more active than that implies. She audited existing programs, mapped the landscape of nonprofit partnerships, interviewed stakeholders across the business, and built a mental architecture for how social impact could connect to HubSpot's strategy. She wanted to understand what mattered to HubSpotters and to the business, and how those priorities might fit together into something coherent.

She also talked to teams running what she calls "social impact tangential" programs — initiatives like First Gens in Tech and HubSpot for Nonprofits, among others. None of them were owned by her team, but each carried a social impact element. Understanding how they worked, and who they served, would prove essential later.

Her instinct, she admits, was to move faster. "I wanted to just jump in and try and get something off the ground as soon as I could. But I knew that wasn't going to work here." She didn't have a SaaS background. She needed the full picture before she could decide what to build inside it.

THE NARROWING

So what do you build when you could build anything?

When it came time to choose a direction for HubSpot's signature program, We Are All Entrepreneurs, Kaiya's first instinct was the obvious one. Help people with limited access understand business fundamentals. Build an accelerator-style offering. It mapped cleanly to HubSpot's mission of helping businesses grow better.

But the more she explored, the less original that idea felt. Several nonprofit partners had already built accelerator models that excelled at helping founders from historically excluded communities get their businesses off the ground. They were doing it well.

When she describes this moment, the word that keeps coming back is clarity. "I knew that our program couldn't be duplicative; it needed to be additive," Kaiya said.

The answer was the platform itself — the specific technology HubSpot builds and knows better than anyone else.

“We’re best positioned to help entrepreneurs learn how to implement tech to grow their businesses. In that way, our program can be an addition, or a ‘next step,’ for the different accelerators that already exist.”

Getting that much narrower meant every piece of programming that followed could tie directly back to what HubSpot actually does.

PERMISSION TO BE IMPERFECT

The thing is, HubSpot moves fast, and you feel that whether you're new or not. Kaiya wanted to be thorough, to really understand the landscape before committing to a direction, but she also felt the pull to keep up. The difference came from a specific, repeated reframe from her manager. You don't have to have everything at 100% to test a theory.

“There were several discussions with my manager where I remember feeling really overwhelmed by the blank space in front of me. I had never built a program like this from scratch, so I naturally had moments where I was really unsure where to go; but I also didn’t want that to come across too much where it felt like I couldn’t handle it.”

The expectation was simple. Ship something and learn from how it lands. This wasn't unique to her manager. The role itself was designed without a playbook, an inherited template, or a committee to approve each step. That permission wasn't something she had to earn. It came with the role.

For someone who hates shipping anything that isn't complete, that environment was both uncomfortable and freeing. Uncomfortable because the safety net of "wait until it's perfect" wasn't available. Freeing because a pilot that didn't “work” was evidence she could use, not a judgment on her ability.

“It almost reassured me that I wasn’t expected to ‘get it right’ from the get go. And I didn’t. We learned so much from our pilot program that has made our sequential offerings that much stronger.”

BUILDING IT LIVE

The first We Are All Entrepreneurs pilot launched in partnership with a nonprofit accelerator. Roughly 17 entrepreneurs who'd completed a program and were ready for their next step, thinking about how to implement technology in their businesses.

It worked. And it didn't work.

HubSpot customers led the live sessions, which meant entrepreneurs got to learn from real business operators who were also platform experts. That element was well received. The content itself, though, was too high-level, too theoretical. The entrepreneurs wanted something more tactical — show me how to use the CRM, help me solve real problems with it.

The other lesson was operational. Cohorts are intensive to run. For a team of one, replicating them across geographies simply wasn't sustainable, and it didn’t allow the program to scale in the way they wanted. If it was going to grow, it needed to be flexible.

A second cohort, focused on students in the UK and Ireland, confirmed both findings. The tactical approach worked. The model still didn't scale. She was coordinating all of it remotely across four time zones, with no co-located team to pressure-test ideas against.

Kaiya had built the thing twice now, and both times it was labor-intensive to replicate. The model needed to be more flexible. What she let go of was the idea that every geography needed the same depth. What worked for one geography, didn’t necessarily have to work for another. By 2026, she'd landed on a hybrid approach — broader workshops across geographies for reach, and one specialized cohort of roughly 20 spots for depth. This year, over 100 people applied for the cohort.

THE QUIET RETURN

Ask Kaiya what she's most proud of, the thing nobody outside the program would know, and she doesn't point to the cohort applications or the workshop attendance. She points to her inbox.

“I’m still in touch with quite a few of the entrepreneurs who went through our program. They’ll reach out and tell me how their businesses are going, or ideas they’re working on.”

She's careful not to overstate HubSpot's role, and that restraint says as much about the culture as anything else in this story. "I'm not saying HubSpot did all of that; we obviously didn't. But to even be in a position where we supported these founders in their business journey is such a privilege."

THE PAGE, STILL BEING WRITTEN

If someone told Kaiya they were starting a new role at HubSpot where they'd be building from scratch, she'd point them back to the discomfort.

Shipping before you feel ready is uncomfortable, especially if you're someone who wants everything polished before it goes out into the world. But it's how things move here. "If you're anything like me and that's a challenge for you, embrace it," she said. "Use that explorer mindset to help you figure out the longevity of your programs."

The blank page she started with isn't blank anymore, but it isn't finished either. The program is still evolving, still being shaped by what each iteration teaches. And she'd tell you that's the point — the permission to get it wrong is what makes it possible to eventually get it right.

Built Different is a series about what actually happens when a company is built on trust, remote-first flexibility, and real autonomy. Each story is told by the person who lived it.