Head of Sales

About Simple

Simple AI is building state of the art voice AI agents for enterprise. Our realistic agents help iconic businesses like Doordash, xAI, and Omaha Steaks handle all kinds of phone operations, from customer support to order intake to lead qualifications. We’re growing revenue like crazy and looking for an Head of Sales to help accelerate our sales motion and close high-impact deals.

Simple AI raised $14M from world-class investors and operators like Y Combinator, First Harmonic, Massive Tech Ventures, Michael Seibel, Jared Friedman, Alexandr Wang, Matt Van Horn, Suhail Doshi, and Scott Wu.

The Team

The founders (Catheryn and Zach) met while running software teams at YC, where they shipped tons of new products for YC founders, including YC’s co-founder matching site. Cat previously worked at Instagram and Facebook and earned degrees in math and computer science at MIT. Zach previously studied computer science and statistics at U Chicago and led software at PEAK6. We have grown into a strong team of 8 and are continuing 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 while hiring and coaching the sales team around you. You will work closely with Product, Engineering, and our customer-facing technical teams to sell a deeply technical product through measurable business outcomes.

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

• Commute Assistance

• Regular team events & offsites

   

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.

If you’re excited to close high-impact deals, shape our GTM motion, and join an early-stage AI startup with massive momentum, we’d love to chat.