George B. Thomas
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We open on a real moment. Courtney Sembler just got engaged over her birthday weekend and still showed up ready to serve. That tells you almost everything about her compass. In this episode, we talk about ambition, humility, strategy, and why empowerment starts inside you and expands to the systems you lead.
Her story matters now because customer education is finally taking center stage in the go-to-market strategy, and Courtney has the receipts to show how to make that shift feel human and work at scale.
Origin to Ops: From Conservation to Customer Education
Courtney’s career began in an environmental nonprofit focused on land conservation in South America. She ran the org’s CRM and learned to coordinate across continents. It was scrappy, mission-driven, and deeply practical. Later, at HubSpot, she started in technical support, moved into internal training, and then to Academy.
Each step layered people, process, and platforms into a craft built around helping humans learn.
Three anchors shaped her: a boardroom memory of her mom, a trailblazing CFO in the early eighties, and a first manager at HubSpot who asked a big question in their very first one-on-one: what do you want to do with your life? Those snapshots show up in how Courtney leads today.
“I do really want to be a leader of a company someday.” — Courtney Sembler
Feedback That Stings and the Space to Grow
Early at HubSpot, a performance review hit hard. She walked in confident and left with a rating that said she was struggling. It hurt. She cried, wrote a resignation letter, slept on it, then chose to stay, absorb the feedback, and change how she worked and communicated.
Two and a half months later, the Academy called with an offer. The lesson was simple and tough. Growth requires time, team over self, and a willingness to rewrite your inner script.
There was another moment.
At a HubSpot User Group in Virginia, an attendee stood up at the start and left, saying he would not learn from a child. Courtney took a breath, used humor to reset the room, and delivered value. Several of those attendees are still connected with her years later. That is resilient leadership in practice.
From Slides to Story and Measurable Retention
As a new manager, Courtney pitched a content strategy she loved. Executives did not. She tried again. Same result. The turning point came in a coaching conversation that reframed the task: reduce the strategy to three slides, then two, then explain it like a five-year-old.
She rebuilt the story so non-educators could clearly see the impact. That shift unlocked a larger win. In 2022, Academy rallied around closing a defined retention gap, partnered cross-functionally, and hit ambitious goals.
Courtney earned the director role, and the Academy’s influence accelerated.
Empowerment in Practice: Create the Space, Own the Voice
Courtney believes empowerment starts within. Leaders and allies cannot empower you, but they can create the space for you to self-empower.
On her monitor is a sticky note with a reminder she returns to daily:
“You are enough. You can do it.” — Courtney Sembler
Her approach to team leadership reflects that belief. Care about the whole person. Know the dog’s name. Make room for emotion. Encourage courageous tries and second drafts.
The result is a culture where people flourish, not just perform.
Looking Ahead with HubSpot: Video, AI, and Academy’s Next Chapter
Courtney sees three practical trends:
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Opinionated video content is finally moving into the center of marketing plans, supported by HubSpot’s tooling.
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Clearer, human-guided AI usage that augments people rather than replaces them.
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An Academy team iterating fast on short-form learning, scalable onboarding, and live education across languages.
All of it adds up to customer education being woven into go-to-market from day one, not added after the sale.
Why It Matters
If you lead in the HubSpot ecosystem, you are not just deploying features. You are shaping habits. Courtney’s story reminds us that strategy is effective when it is simple, relatable, and measurable.
Education is not a side quest. It is the operating system for retention, adoption, and joy at work.
Reflect & Act
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Is your strategy too complex to inspire action in two slides or less?
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How will you create space this quarter for your team to self-empower?
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What one opinionated video series will you launch to teach your best practice?
