Head of Sales

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 20+ 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
• Late night Ubers
• 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.

Additional information

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.

Please note: At this time, Simple AI is unable to provide employment visa sponsorship for this role. We appreciate your interest and understanding.