I’m passionate about leading mission aligned teams at the intersection of growth and social impact. 

As a revenue and growth executive, I specialize in building and scaling high-performance teams, driving go-to-market strategy, and leading business transformation for VC, PE-backed, private, and public companies. 

As a leader, I invest in mentoring and coaching high-performing teams who over-deliver for both clients and the organization.

My focus is on accelerating ARR, penetrating enterprise and mid-market segments, and fueling sustainable revenue expansion through data-driven sales execution and strategic partnerships.

I bring deep expertise in revenue architecture, from ground-up builds to high-growth and building repeatable scale, along with experience integrating people, processes, and products during M&A. 

I excel at creating upstream GTM motions, increasing average contract value, and delivering consistent year-over-year growth across SaaS, services, and multi-product portfolios.

Career Highlights:

Grew global revenue from $20M to $55M+ by increasing organic top line sales from $7.4M to $20.7M in 2 years, resulting in a successful exit.

Secured a $74M strategic partnership to build and scale 36 university programs.

Led team to close 50 new enterprise deals, increasing ACV from $14K to $46K through upstream GTM motion.

One of the first sales leaders at a pre-seed SaaS startup, helping drive initial revenue that supported a successful $38M Series A raise.

Outside of work, I’m a lifelong learner who loves connecting with people, exploring new places, and experiencing different cultures. I find energy in great conversations, outdoor walks with a good podcast, and the occasional Peloton ride. As a sports enthusiast and natural connector, I’m always looking for ways to bring people, ideas, and opportunities together.

I’m thrilled to share that I’ve joined Learning.com as Chief Growth Officer!

The definition of what it means to be "future-ready" is shifting rapidly and expectations reach far beyond teaching kids to master the latest tech tool. 

I am energized by the work that Lisa O'Masta and the Learning.com team are doing to empower students to have a healthy and proficient relationship with technology. 

By the time K-12 students graduate, there will be an expectation that they understand how to engage with digital systems responsibly, critically think about the information they encounter, and navigate AI-enabled environments with judgment and integrity.   

Digital literacy, AI literacy, and Media Literacy are no longer separate skills or conversations. They’re foundational skills that shape how students learn, assess information, and participate in the world.  

Learning.com empowers students with these skills and confidence to engage as digital citizens long before high school, when the stakes and expectations ultimately are higher. 

This is an incredible team, many of whom are prior educators and administrators, who act as true partners to districts and states to build these essential student skills EARLY, thoughtfully, and at scale. 

I’m grateful to join a team so deeply committed to students, educators, and the communities they serve and am excited to help expand the impact of this critically important work!

Kelly Crabb

Revenue & Growth Leader | AI + Education | Advisor

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