Head of Sales
About the Team
Simple AI is building state-of-the-art voice AI agents for enterprise, helping iconic businesses like Doordash, xAI, and Omaha Steaks handle phone operations from customer support to order intake to lead qualification. The company has raised $14M from investors including Y Combinator, First Harmonic, Massive Tech Ventures, Michael Seibel, Jared Friedman, Alexandr Wang, Matt Van Horn, Suhail Doshi, and Scott Wu.
The founders, Catheryn and Zach, met while running software teams at YC. Cat previously worked at Instagram and Facebook and holds degrees in math and computer science from MIT. Zach studied computer science and statistics at U Chicago and led software at PEAK6. Simple AI has grown into a strong team of 20+ and continues to scale quickly.
About the Role
We are hiring our first Head of Sales to partner directly with our CEO and lead Simple's next phase of enterprise growth. You will own the revenue number, personally lead our most important deals, and turn our early sales motion into a repeatable engine. This is a hands-on player-coach role—not a position for someone who wants to manage from the sidelines.
You will:
- Prospect, run discovery, shape business cases, navigate complex buying committees, negotiate, and close
- Hire and coach the sales team around you
- Work closely with Product, Engineering, and customer-facing technical teams to sell a deeply technical product through measurable business outcomes
What You'll Need
- 7+ years of B2B SaaS sales experience, including experience leading or coaching quota-carrying sellers in an early-stage or high-growth company
- A track record of personally exceeding seven-figure annual quotas and repeatedly closing six-figure enterprise deals
- Experience building a sales motion, territory, team, or playbook from an early stage—not only operating inside a mature sales organization
- Strong enterprise deal judgment across outbound, multi-threaded discovery, executive alignment, technical evaluations, security, legal, and procurement
- Rigorous pipeline management and forecasting skills, paired with the willingness to get on calls and show the team what great selling looks like
- High agency, urgency, low ego, and excitement to work in person with the team in San Francisco
Nice to Have
- Experience selling AI, automation, developer tools, or another technical enterprise product
- Experience selling to contact center, customer experience, operations, or revenue leaders
- Experience partnering closely with founders, engineers, Forward Deployed Engineers, or Solutions Engineers on complex deals
What We Offer
- Competitive salary & meaningful equity
- Employee-friendly equity terms
- An office located in SF
- Health, dental & vision insurance
- Free lunch & dinner at the office
- Late night Ubers
- Regular team events & offsites