Head of Sales
About The Position
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.
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—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
- 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
Nice To Haves
- 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
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 our customer-facing technical teams to sell a deeply technical product through measurable business outcomes
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
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What This Job Offers
Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed
