This listing does not state pay. Across 42 open head of sales listings that state pay, the middle half runs $164,500 to $270,000 and the median is $209,500.

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Share of this job’s tasks that AI is already used for at work, from real usage. It is not a forecast of job loss, and a low number means no use seen yet. Source: Anthropic Economic Index.

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About the job

Position: Head of Sales

Who is Automat?

Automat was founded by a diverse group of creative technologists from teams like Google Creative Lab and Samsung’s Innovation Think Tank. We're building a future where intelligent agents run real business operations, not just support them. Automat Workforce puts AI coworkers directly inside a company's existing tools to handle day-to-day operational work, and our Studio platform gives customers a fully managed way to build, deploy, and monitor their own agents and automations.

We value curiosity, collaboration, and impact above rigid requirements. If you’re excited about AI and automation, thrive in flexible, creative environments, and want to work on meaningful, pioneering projects -- this role is for you.

The Role

We’re looking for a hands-on sales leader who thrives at the intersection of product, customer, and technical narrative. You’ll work closely with our CEO and founding team to shape our go-to-market strategy, run high-conviction experiments, and bring our AI products into the hands of real customers at an enterprise scale. This is not a pure management role -- you’ll be in the trenches helping close deals, distill technical value into business outcomes, and lay the foundation for a scalable, product-centric sales motion.

You’ll also work alongside engineers and designers to translate user needs into product priorities, develop repeatable playbooks, and tell the story of what Automat unlocks for the enterprise.

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