Coaching at Scale: How LevelUp Grew Toward $500M with a 5-Person Sales Team

Recorded live as the first session of our Revenue Execution Roundtable, a monthly peer-driven discussion series for sales leaders, enablement teams, and frontline managers in the Airspeed community.

Airspeed customer Grant Jessup, Chief Client Officer & SVP at LevelUp HCS, shares how a lean, high-performing sales team is using AI-powered coaching to drive consistency, accelerate rep development, and close more revenue, without adding headcount.

Grant leads the Sales organization at LevelUp HCS, a global RPO firm growing toward $500M with a five-person sales team. He walks through practical examples of what’s working in the field: from how his team uses scorecard data to spot patterns and focus training, to building a culture where reps take ownership of their own development.

Expect real examples from a team that coaches at scale every day, plus an open discussion on what’s working across other revenue organisations.