About the role
Leland’s mission is to unlock human potential by making the world’s expertise more accessible. Our platform connects ambitious people with coaching, content, and courses that can can help them achieve their career and educational goals. Since our founding in 2021, we’ve helped tens of thousands of people reach their most ambitious goals, raised $19M from world-class investors, and built the industry leader in educational, career, and AI coaching. Leland is hiring its first-ever Head of Sales to own, lead, and build our entire revenue organization, spanning both our B2B business and our consumer sales motion. This is a player-coach role: you will take demos and close deals with employers and universities, hire and train a team of B2B reps, and lead a consumer sales team selling coaching packages and bootcamps directly to individuals. You will work directly with the leadership team to shape Leland's go-to-market strategy, and you will own the full revenue lifecycle: net new business, onboarding, renewals, and expansion. This role is right for someone whose scope has grown at every stage of their career. You've been a top performer. You've built and led a team. You understand what great looks like from every seat in a sales org. You'll define how we sell, who we hire, and what winning looks like for years to come.
Responsibilities Sell Carry a personal book of business and own the most complex, high-value deals across our employer and university verticals Take demos, run discovery, and close contracts, serving as the senior presence in high-stakes sales conversations Work cross-functionally with Growth, Product, and Operations to convert pipeline and refine how Leland is positioned in the market Set strategy and direction for Leland's consumer sales motion, coaching
the team toward consistent performance across product lines with varying margin and volume profiles Build Design and document Leland's end-to-end B2B sales process, from initial outreach through close and handoff to Account Management Build and own our Sales Operations infrastructure: CRM hygiene (HubSpot), pipeline reporting, forecasting, and performance dashboards Develop playbooks, training materials, and onboarding frameworks that will enable future hires to ramp quickly Establish rules of engagement,
