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Outset is an AI-powered user research platform used by global enterprises like HubSpot, Microsoft, Uber, and Nestle to conduct qualitative research at scale. The company recently raised a $30M Series B (December 2025) and is experiencing rapid growth with 8x business expansion.
You will lead a team of Enterprise Account Executives, owning team performance, pipeline output, and quota attainment. Key responsibilities include:
- Managing and coaching Enterprise AEs through pipeline reviews, deal strategy, forecasting, and 1:1 development
- Recruiting, hiring, and onboarding new AEs as the team scales
- Partnering with Marketing and Customer Success on enterprise account strategy and expansion
- Getting directly involved in complex, high-value deals—providing negotiation support, building exec-level relationships, and developing deal strategy alongside your reps
- Building and refining sales processes, playbooks, and enablement materials for the enterprise segment
- Identifying and addressing performance gaps through coaching and performance management
- Reporting on team metrics, pipeline health, and win/loss trends to leadership
You'll operate in a lean, fast-growing startup environment where you'll have autonomy to shape the enterprise sales motion. This role requires someone who can both manage and coach effectively while staying hands-on with complex deals.
Required experience: 5+ years in enterprise or complex B2B sales with at least 3+ years directly managing an AE team. Ideally, you have experience in the user or market research space. You should have a track record of hitting or exceeding team quota in high-velocity environments, strong coaching instincts, and experience building or refining sales processes—not just executing existing ones. You're comfortable in a startup setting with evolving infrastructure and can communicate effectively with both internal leadership and C-level enterprise buyers.
