Head of Sales - Onsite

Our client, an AI-driven enterprise B2B startup, is seeking a Head of Sales.

We are looking for a hands-on, player-coach sales leader who thrives at the intersection of product, customer insight, and technical storytelling. You'll partner directly with the CEO and founding team to define go-to-market strategy, run high-conviction experiments, and drive enterprise adoption of a category-defining AI platform.

This is not a pure management role. You will be in the trenches — closing complex enterprise deals, translating technical capabilities into business value, and building the foundation for a scalable, product-led sales motion.

You'll collaborate closely with engineering and design to turn real customer feedback into product priorities while developing repeatable sales playbooks that support long-term growth.

What You'll Do

Lead early sales efforts across product-led, outbound, and inbound channels
Partner with the CEO and CTO on customer targeting, deal execution, and revenue strategy
Own the full enterprise sales cycle — from use-case discovery and demo to contract negotiation and close
Translate complex AI infrastructure and technical functionality into clear, compelling business narratives
Design and implement scalable GTM processes, tooling, and territory plans
Build and mentor a high-performing sales team while continuing to close strategic deals
Feed structured customer insights back into product, engineering, and design

What Were Looking For
6–10 years of experience selling technical enterprise software, with early-stage startup exposure
Proven track record of exceeding quota (Presidents Club, rapid promotions, consistent overperformance)

Experience leading enterprise sales and building teams in a Seed–Series B/C environment
Strong player-coach mindset with the ability to close complex deals while managing and developing talent
Experience selling into RPA or automation markets
Ability to build outbound strategy, manage inbound/product-led pipeline, and create scalable sales processes
Clear, confident communicator who can engage engineers, operators, and executives alike
Familiarity with the AI ecosystem (e.g., OpenAI, Anthropic, vector databases, LLMOps) is a plus

This is an opportunity for a competitive, strategic sales leader who wants to help define a category and scale enterprise revenue from the ground up.

Location: SFO (SFO), San Francisco, CA, USA

Skills required for this job:

• CRM tools
• Enterprise sales
• Go-to-market strategy (GTM strategy)
• Inbound sales
• Outbound sales
• Robotic process automation (RPA)
• Sales
• Sales management
• Sales strategy
• Technology sales