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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 where you will prospect, run discovery, shape business cases, navigate complex buying committees, negotiate, and close while hiring and coaching the sales team. You will work closely with Product, Engineering, and customer-facing technical teams to sell a deeply technical product through measurable business outcomes.
Responsibilities
- Own the revenue number
- Personally lead our most important deals
- Turn our early sales motion into a repeatable engine
- Prospect
- Run discovery
- Shape business cases
- Navigate complex buying committees
- Negotiate
- Close deals
- Hire and coach the sales team
- Work closely with Product, Engineering, and customer-facing technical teams
Requirements
- 7+ years of B2B SaaS sales experience
- 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
- Repeatedly closing six-figure enterprise deals
- Experience building a sales motion, territory, team, or playbook from an early stage
- Strong enterprise deal judgment across outbound, multi-threaded discovery, executive alignment, technical evaluations, security, legal, and procurement
- Rigorous pipeline management and forecasting skills
- Willingness to get on calls and show the team what great selling looks like
- High agency, urgency, low ego
- Excitement to work in person with the team in San Francisco
Skills
- B2B SaaS sales
- Sales leadership
- Sales coaching
- Enterprise deal closing
- Sales motion building
- Territory building
- Team building
- Playbook creation
- Outbound sales
- Multi-threaded discovery
- Executive alignment
- Technical evaluations
- Security review
- Legal review
- Procurement negotiation
- Pipeline management
- Forecasting
- Selling AI
- Selling automation
- Selling developer tools
- Selling technical enterprise products
- Selling to contact center leaders
- Selling to customer experience leaders
- Selling to operations leaders
- Selling to revenue leaders
- Partnering with founders
- Partnering with engineers
- Partnering with Forward Deployed Engineers
- Partnering with Solutions Engineers
Location
- SF
- San Francisco
Work Type
- In person
Experience Level
- 7+ years of B2B SaaS sales experience
- Experience leading or coaching quota-carrying sellers
- Experience building a sales motion, territory, team, or playbook from an early stage
Salary/Compensations
- Competitive salary & meaningful equity
Benefits
- Competitive salary & meaningful equity
- Employee-friendly equity terms
- Health, dental & vision insurance
- Free lunch & dinner at the office
- Commute Assistance
- Regular team events & offsites
About the Company
- 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 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