Head of Founder Success, Learning & Retention (SLR)

Careerscape is recruiting on behalf of our client, a venture investment and startup growth platform, for a Head of Founder Success, Learning & Retention (SLR) to lead the function that keeps portfolio founders engaged, supported, and thriving long after the initial investment is made. This is a rare opportunity to build and own a founder-facing discipline from the ground up, shaping how an ambitious platform supports the entrepreneurs it backs across every stage of the startup lifecycle.

Day to day, this role feels part community builder, part strategist, and part coach. You will spend your time designing learning programs, checking in with founders navigating hard decisions, and translating what you hear on the ground into programs and policy that improve retention and satisfaction across the portfolio. People who thrive here have genuine empathy for the founder journey, are comfortable operating with autonomy, and enjoy building repeatable systems out of what starts as ad hoc relationship management.

Responsibilities

• Design and lead founder success, onboarding, and learning programs across the portfolio
• Serve as the primary relationship owner for founders navigating growth, funding, and operational challenges
• Build and manage curricula, workshops, and peer learning cohorts tailored to founder needs
• Develop and track founder satisfaction, engagement, and retention metrics
• Partner closely with the investment team to align founder support with portfolio company goals
• Create onboarding journeys for newly funded founders joining the platform
• Recruit, coordinate, and manage a network of mentors, coaches, and subject matter experts
• Manage and develop a small team of founder success and program managers
• Represent the organization at founder-facing events, summits, and community gatherings
• Continuously refine programs based on founder feedback and outcome data

Requirements

• 8+ years of experience in venture capital, startup accelerators, or founder-facing roles
• Proven track record building or scaling founder success, community, or portfolio support programs
• Strong relationship management and coaching skills with startup executives
• Deep understanding of the startup lifecycle from seed through growth stage
• Experience designing learning curricula or professional development programs
• Excellent verbal and written communication skills
• Experience managing and developing a team
• Bachelor's degree required, advanced degree a plus
• Willingness to travel for founder events and portfolio visits

Benefits

• Medical, dental, and vision insurance
• 401k with company match
• Generous paid time off and company holidays
• Annual professional development budget
• Performance bonus and equity potential
• Parental leave program
• On-site wellness and commuter benefits
• Collaborative, founder-obsessed team culture
• Regular offsites and portfolio community events