Head of Sales
Hands-on sales leader shaping GTM strategy for AI enterprise products, leading full sales cycles from targeting to closing, and collaborating with CEO/CTO on revenue experiments. Requires 4-8+ years B2B sales experience with technical fluency in AI/ML.
About the job
What You’ll Do
- Lead early sales efforts across both product-led and outbound/inbound motions
- Partner with the CEO and CTO on customer targeting, deal execution, and revenue strategy
- Lead the full sales cycle -- from mapping use cases to demoing product to closing contracts
- Translate complex product functionality and AI infrastructure into compelling narratives for technical and non-technical stakeholders
- Build internal tooling, templates, and playbooks to make GTM efforts more scalable
- Feed insights from customer conversations back into product, engineering, and design
What Drives You
- You’re a builder at heart -- energized by creating systems, not inheriting them
- You want to get deep into the product and understand how it works under the hood
- You believe the best sales strategy starts with understanding real problems
- You’re comfortable with ambiguity, fast feedback loops, and wearing multiple hats
- You love figuring out what makes technical buyers tick -- and earning their trust
What’s in Your Toolbox
- Strong technical fluency -- you’ve sold technical products to data teams, operators, or engineers and can hold your own in a room full of builders
- Experience selling complex B2B software, ideally at an early-stage startup or within an emerging tech category (AI, ML, automation, etc.)
- Ability to design and execute outbound strategies as well as manage inbound and product-led pipelines (ability to build out territory plans, top of funnel strategy)
- A knack for demoing and storytelling -- you can walk someone through a workflow and connect it to business value in seconds
- Familiarity with the AI ecosystem (e.g., OpenAI, Anthropic, vector DBs, LLMOps) is a strong plus
- Comfortable using modern GTM tools and experimenting with automation and AI in your own workflow
What We’re Looking For
- Clear, thoughtful communicator who can talk to engineers, operators, and execs alike
- High-agency operator who’s comfortable iterating and improvising in public
- Passion for AI, automation, and building things that make people’s jobs easier
- Experience navigating high-velocity sales cycles and complex enterprise deals
- 4–8+ years of experience in B2B sales, ideally with 2–5 years in a player/coach or management capacity
- Previous experience in startups or dynamic, high-growth environments
Skills
B2B Sales, Ai Ecosystem, Outbound Sales, Product-Led Growth, Gtm Tools, Demoing, Storytelling, Enterprise Sales, Sales Playbooks, Llmops
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