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Simple AI is building state-of-the-art voice AI agents for enterprise customers. The company's realistic agents help iconic businesses like DoorDash, xAI, and Omaha Steaks handle phone operations including customer support, order intake, and lead qualification. Simple AI raised $14M from top-tier investors including Y Combinator, First Harmonic, Massive Tech Ventures, and prominent operators like Michael Seibel and Jared Friedman. The founding team includes Catheryn (formerly Instagram/Facebook, MIT math and CS) and Zach (formerly PEAK6, University of Chicago CS and statistics), who met while running software teams at YC. The company has grown to 8 team members and is scaling rapidly.
You will be hired as Simple AI's first Head of Sales, partnering directly with the CEO to lead the company's next phase of enterprise growth. This is a hands-on player-coach role requiring you to own the revenue number, personally lead major deals, and transform early sales motion into a repeatable, scalable engine. You will prospect, conduct discovery, shape business cases, navigate complex buying committees, negotiate, and close deals while simultaneously hiring and coaching the sales team around you. Close collaboration with Product, Engineering, and customer-facing technical teams is essential to selling this deeply technical product through measurable business outcomes.
Required qualifications include 7+ years of B2B SaaS sales experience with a track record of leading or coaching quota-carrying sellers in early-stage or high-growth companies. You must have personally exceeded seven-figure annual quotas and repeatedly closed six-figure enterprise deals. Experience building a sales motion, territory, team, or playbook from early stage is critical—not just operating within mature sales organizations. You need strong enterprise deal judgment across outbound prospecting, multi-threaded discovery, executive alignment, technical evaluations, security, legal, and procurement. Rigorous pipeline management and forecasting skills are essential, paired with willingness to get on calls and model great selling for your team. High agency, urgency, low ego, and commitment to working in-person in San Francisco are required.
Nice-to-have qualifications include experience selling AI, automation, developer tools, or other technical enterprise products; selling to contact center, customer experience, operations, or revenue leaders; and partnering with founders, engineers, Forward Deployed Engineers, or Solutions Engineers on complex deals.
