PeopleConnect Staffing
Head of Sales
Location: San Jose, CA
Compensation: $200,000 - $250,000/year
Our client has developed an AI-native operating system for modern restaurants. Their system unifies everything in one place – POS, payroll, scheduling, accounting, marketing campaigns, inventory, and purchasing – so teams can run smarter, faster, and more profitably with a single, intelligent platform.
They are currently seeking an experienced and motivated Head of Sales to join their team.
As their first Head of Sales, you’ll define how we scale from early traction to $10M+ in the next year. You’ll own the full revenue function – you'll shape how the sales process is structured, how the team is built, and how restaurants adopt AI for the first time. You’ll operate as a player‑coach in the early days – closing your own deals to shape the sales playbook – while coaching the existing sales team on a repeatable, scalable sales motion.
This role will be based in their San Jose office, and report directly to the CEO.
As the Head of Sales, you will:
Own and execute the path from early traction to $10M+ ARR in the next year – with 500+ restaurants on the platform by the end of 2026.
Recruit, hire, and develop a world‑class sales team with a servant leadership approach. Expand the team beyond the Bay Area in 2H by identifying and training regional sales managers in expansion cities.
Become obsessed with the ideal customer profile and develop playbooks for scalable, repeatable deals.
Lead by example by closing your own deals while coaching your team. Deeply learn and understand the prospective customer and field sales approach.
Collaborate closely with Product, Marketing, and Customer Success to advocate for the needs of prospective and existing customers. Drive pricing and packaging evolution as we add new products. Bring customer insights back to influence product roadmap.
Build scalable sales processes that use AI and automation to drive the most efficient field sales team.
As the Head of Sales, your background should include:
Minimum 7+ years of progressive sales leadership experience with proven success in scaling B2B companies from $1M to $10M+ ARR.
Experience building and developing a world‑class sales team through a servant leadership approach, especially in a product that requires a field sales approach.
Hands‑on execution mindset – willing to close your own deals, not just manage others. Proven record of personal quota achievement alongside team leadership.
AI fluency with demonstrated ability to articulate how AI impacts sales teams and how to incorporate it into sales operations.
Experience working closely with VC‑backed founders and thriving in high‑intensity environments.
Nice to Have:
Experience in restaurant technology.
If you’re interested in learning more, please send your resume to adam@peopleconnectstaffing.com.
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Compensation: $200,000 - $250,000/year
Our client has developed an AI-native operating system for modern restaurants. Their system unifies everything in one place – POS, payroll, scheduling, accounting, marketing campaigns, inventory, and purchasing – so teams can run smarter, faster, and more profitably with a single, intelligent platform.
They are currently seeking an experienced and motivated Head of Sales to join their team.
As their first Head of Sales, you’ll define how we scale from early traction to $10M+ in the next year. You’ll own the full revenue function – you'll shape how the sales process is structured, how the team is built, and how restaurants adopt AI for the first time. You’ll operate as a player‑coach in the early days – closing your own deals to shape the sales playbook – while coaching the existing sales team on a repeatable, scalable sales motion.
This role will be based in their San Jose office, and report directly to the CEO.
As the Head of Sales, you will:
Own and execute the path from early traction to $10M+ ARR in the next year – with 500+ restaurants on the platform by the end of 2026.
Recruit, hire, and develop a world‑class sales team with a servant leadership approach. Expand the team beyond the Bay Area in 2H by identifying and training regional sales managers in expansion cities.
Become obsessed with the ideal customer profile and develop playbooks for scalable, repeatable deals.
Lead by example by closing your own deals while coaching your team. Deeply learn and understand the prospective customer and field sales approach.
Collaborate closely with Product, Marketing, and Customer Success to advocate for the needs of prospective and existing customers. Drive pricing and packaging evolution as we add new products. Bring customer insights back to influence product roadmap.
Build scalable sales processes that use AI and automation to drive the most efficient field sales team.
As the Head of Sales, your background should include:
Minimum 7+ years of progressive sales leadership experience with proven success in scaling B2B companies from $1M to $10M+ ARR.
Experience building and developing a world‑class sales team through a servant leadership approach, especially in a product that requires a field sales approach.
Hands‑on execution mindset – willing to close your own deals, not just manage others. Proven record of personal quota achievement alongside team leadership.
AI fluency with demonstrated ability to articulate how AI impacts sales teams and how to incorporate it into sales operations.
Experience working closely with VC‑backed founders and thriving in high‑intensity environments.
Nice to Have:
Experience in restaurant technology.
If you’re interested in learning more, please send your resume to adam@peopleconnectstaffing.com.
#J-18808-Ljbffr