# Head of Sales

**Company:** [Automat](https://hotfix.jobs/companies/automat)
**Location:** San Francisco, CA
**Role:** Executive Leadership
**Experience:** 4+ years
**Skills:** B2B Sales, Ai Ecosystem, Outbound Sales, Product-Led Growth, Gtm Tools, Demoing, Storytelling, Enterprise Sales, Sales Playbooks, Llmops
**Posted:** 2025-11-06

> 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.

## Job Description

## 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

## Similar roles

- [Director, Major Sales](https://hotfix.jobs/jobs/514795d2-324c-40c5-9e37-5a9171894ee3) - Vercel - New York, NY - $380k – $430k/yr
- [Senior Director, Field CTOs](https://hotfix.jobs/jobs/b0498b9e-9c6a-487c-aae0-35bae099df36) - GitLab - Remote - $244k – $410k/yr
- [Director, International Strategy & Planning](https://hotfix.jobs/jobs/ed129139-a790-4058-9880-b7113d436e18) - Instacart - Remote - $206k – $262k/yr
- [Head of Marketing, IT](https://hotfix.jobs/jobs/4e9a27ac-2a03-4594-b3ff-67c4ec0732bf) - Rippling - San Francisco, CA - $186k – $310k/yr
- [Head of GTM & Revenue](https://hotfix.jobs/jobs/6136a67e-66f8-4236-991d-a4441c568c5b) - Electronx - New York, NY - $200k – $250k/yr

**Apply:** https://hotfix.jobs/jobs/ab5f982f-24d7-49d1-8316-440a721a92c6
**Canonical:** https://hotfix.jobs/jobs/ab5f982f-24d7-49d1-8316-440a721a92c6