George B. Thomas
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Kristen Granara walks into a room as herself. Not a polished version. Not a performance. Not a “safe” version that fits someone else’s idea of professional.
And that matters, because when you hear her story, you realize her success is not just about skills. It is about choices. The kind you make when life gets loud, when fear shows up, and when you decide you are done shrinking.In this Women of HubSpot episode, I sat down with Kristen, Senior Manager of HubSpot Academy Learning Operations at HubSpot. We talked about the moments that shaped her, the turns she did not plan for, and the leadership lessons she earned the honest way.
Kristen shows you how to stay authentic in a world that loves to sand people down, how to build systems that serve humans, and how to lead by finding the spark that helps someone empower themselves.
The moment that changed everything
Some life moments do not ask for your permission. They just arrived. Kristen was working at the Apple store on Boylston Street in Boston. If you know the city, you know what that means. It is right there near the Boston Marathon finish line.
She took the day off. She went to the finish line. Then she stepped into the store for what should have been a quick break. And then everything changed.
What hit her next was not just fear. It was clarity. The kind that cuts through noise and exposes what matters. She said it straight: “Life is too short. I am done thinking about these little stressors”. That sentence is not a quote you forget. Because it is not a slogan. It is a line in the sand.
After that day, she started noticing things she had tolerated without question. Long shifts. Weekends. Holidays. The slow drip of stress that can convince you this is the price of being responsible.
And she decided she was done paying that price.
She left Apple. She explored. She worked a couple of other roles. And then she got an email about a job at HubSpot. Here is the part I love: it was not random. She had been building toward this without realizing she was building toward it.
Her path was forming her. And when HubSpot showed up, she was ready.
How she leads, builds, and uses HubSpot in the real world
Kristen does not lead by hype. She leads by clarity. She joined HubSpot Academy and quickly became the first learning and development specialist on the team. Which sounds exciting, because it is. But it also means you are building the plane while you are flying it.
She had a vision for what great learning could look like. She cared deeply about the craft. But she also hit a very human wall.
Her message was not always landing.
If you have ever been the person in the room who sees what could be better, but cannot get traction, you know what that feels like. It is frustrating. It can mess with your confidence. Then something shifted.
She had a conversation with a leader named Courtney. Kristen shared what she really wanted, not just for herself, but for the people around her. She wanted every professor to become an excellent instructional designer. Skills they could carry anywhere, long after the job title changes.
And the response was essentially: go do it.
Not in a reckless way. In a trusted way. In a “build the impact and let the results speak” kind of way.
That permission changed how Kristen moved.
She started shaping learning operations in a way that protected the professors and made excellence easier to repeat. She built a system where professors could focus on creating great content, then hand it off to operations, and know it would be handled with care.
That is real leadership. Not controlling every step. Not demanding perfection. Creating a structure that lets people do their best work without burning out. And I have to say this part, because it is a powerful thread in her story.
Early on, people told Kristen she needed to get rid of her Boston accent to be successful as a trainer.
Let that sink in. The message was: be less you if you want to be taken seriously.
She did not take the deal.
She stayed herself.
And later, she saw what happens when you stop trying to edit your humanity. That very thing people criticized became part of what audiences connected with.
Connect with Kristen Granara on LinkedIn.
The lesson she wants you to carry forward
Kristen kept returning to a truth that I want you to hear loud and clear.
Empowerment is personal.
You cannot motivate everyone the same way. You cannot copy and paste your own drive onto another human and expect it to work. Kristen said it like this: “figuring out what's that little spark of inspiration for someone.”
That is the leadership move.
- You look at the human in front of you.
- You listen.
- You notice what lights them up.
- Then you help them take a step toward it.
Not because you need them to produce. Because you actually care who they become.
And if you are building a team, leading a department, or trying to grow a business, hear me on this: the fastest way to build something real is to stop treating people like parts.
Build systems that support humans.
Lead with clarity and care. And do not ask people to erase themselves to fit your comfort zone.
Frequently asked questions
What does learning operations do at HubSpot Academy?
Learning operations builds the behind-the-scenes process and support so educators can focus on teaching while the operational team handles what makes learning scale well.
How did Kristen respond when people told her to change her Boston accent?
She stayed herself. Over time, she saw that what some people criticized actually helped audiences connect with her.
How does Kristen think about empowering people?
She believes empowerment starts by finding what inspires someone personally, then helping them empower themselves instead of trying to motivate everyone the same way.
About the guest
Kristen Granara is the Senior Manager of HubSpot Academy Learning Operations at HubSpot. She started in graphic and web design, grew into training through Apple, and then moved into building scaled learning experiences at HubSpot Academy. Today, she helps create systems that support educators and protect the human side of learning.
Connect with Kristen Granara on LinkedIn.
Take Action Now
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Run the “spark” conversation with one person this week.
Ask: “What part of your work gives you energy?” and “What drains you?”
Then choose one small change you can make in the next 7 days that protects their energy and grows their confidence. -
Build one process that removes stress, not humanity.
Pick one repeating pain point in your work or team. Handoffs, approvals, content creation, training, and onboarding.
Write a simple “how it works now” and “how it should work” in plain words.
Then test one improvement for a week. -
Stop editing yourself in one meaningful way.
Notice where you are polishing your voice, hiding your style, or shrinking to fit.
Choose one moment this week to show up as you, on purpose. In a meeting, in a training, in a post, in a hard conversation.
