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Sales leadership

Head of GTM (AI Agents)

Bolder Apps logoBolder AppsRemote from United StatesContractListed 2w ago

The posting

We're hiring for our partner company, an early-stage startup building an AI coworker: an agent that lives inside a team's everyday tools and actually gets work done. They need a Head of GTM to take it to market. You'll own the story, the first customers, and the first real revenue. This is a founding role and a hands-on one. You'll write the positioning, run the early sales calls, and build the engine that brings in the next hundred customers. Later, you'll hire the team around it. The role is remote-friendly anywhere in the US, and hours that overlap with Pacific time will make the founder very happy. If you've taken a technical product from zero to paying customers and want to do it again from day one, read on.

About the company

The company is building an AI coworker for teams. It joins the tools a team already uses, picks up context, and handles real work across them. It knows when to act, when to ask, and when to stay quiet. You'll join a seasoned founder and a founding team who spent years building technology in the services world. They watched clients ask for agents long before anyone could deliver them, so they know where the real demand is. The team is small on purpose. The engineers are building fast. Now the company needs one person to own how the product meets the market.

Responsibilities

  • Own positioning and messaging. Decide who this is for, what problem it solves, and how we say it
  • Define the ICP, then prove it or drop it with real conversations and real data
  • Run pricing and packaging experiments. Learn fast from what buyers actually pay for
  • Build outbound from scratch: lists, sequences, first calls, and a clean handoff from founder-led sales
  • Land the first design partners and turn them into paying customers, references, and product feedback
  • Close the first real revenue yourself
  • Stand up a demand-gen and content engine: launches, writing, demos, and showing up where buyers already are
  • Work side by side with the founder and the founding engineers. Bring what customers say back into the product
  • Set up a simple GTM stack and the few metrics that tell us what is working
  • Hire and lead the GTM team once the motion is proven

Our Culture & Values (read before applying)

We move fast. We take ownership. We work with AI, not against it. And we expect everyone to bring ideas, not wait for instructions.

There are no daily checklists, no micromanagement, and no corporate politics. You get autonomy, trust, and a small team that's always ready to help you grow. Here, impact matters more than titles, and curiosity matters more than seniority.

If you want to level up fast and see your work in real users' hands, welcome aboard.

Requirements

  • You've taken a B2B product from zero, or close to it, to its first paying customers. You closed a real share of those deals yourself
  • You've sold technical products: AI, developer tools, APIs, or B2B SaaS bought by technical teams
  • You're comfortable with technical buyers. You can run the demo, follow the architecture questions, and know when to bring in an engineer
  • You've owned positioning, ICP, and pricing work, not just executed someone else's plan
  • You're a player-coach. You write the emails, run the calls, and build the process yourself
  • You use AI tools in your own daily work, and you can tell real agent value from hype
  • You work well from a fuzzy brief, decide with data, and show results in weeks, not quarters
  • Excellent written and verbal communication; you can explain the product to a skeptical buyer and the pipeline to a founder without a slide deck

Nice to have

  • You were one of the first GTM hires at a startup that went on to raise or scale
  • Experience selling AI agents, automation, or workflow tools
  • Product-led growth alongside a sales motion
  • You've built a content or community engine that created real pipeline
  • A network among engineering leaders, ops leaders, or startup founders
  • You've hired and managed SDRs or AEs before

Benefits

  • A founding seat. You own go-to-market and shape how the company sells
  • Founding equity
  • A direct line to the founder and the founding engineers, with no layers in between
  • Remote anywhere in the US, ideally keeping hours that overlap with Pacific time
  • The tools you need to run real GTM experiments
  • A small, experienced team that trusts you to run your own work
  • The chance to build and lead the GTM team as the company grows

Where you can sell from

Fully remote, for people based in United States.

Taken from Bolder Apps's own posting, last seen live on 3 Nov 2026.

The application

Your details and CV, then 10 questions (1 written).

Have readyCVPhoto (optional)
  1. 1.
    EducationShort answer · optional
  2. 2.
    ExperienceShort answer · optional
  3. 3.
    What is your desired HOURLY compensation in USD?Number
  4. 4.
    Where are you based? Country and US state.Short answer
  5. 5.
    Are you legally authorized to work in the United States without visa sponsorship, now or in the future?Yes or no
  6. 6.
    Which of these have you sold yourself, as a quota-carrying seller or GTM owner? Select all that apply.Pick any: 6561169 · 6561170 · 6561171 · 6561172 · 6561173
  7. 7.
    At an early-stage company, how much new revenue did you personally close in your first 12 months?Pick one: 6561174 · 6561175 · 6561176 · 6561177 · 6561178
  8. 8.
    Which of these have you personally owned from scratch? Select all that apply.Pick any (8 options)
  9. 9.
    What is the highest level of AI use you have actually done? Levels are cumulative. Level 6 only counts if you have also done levels 1 through 5. Using a lightweight agent alone does not count as level 6.Pick one: 6561187 · 6561188 · 6561189 · 6561190 · 6561191 · 6561192
  10. 10.
    Share a link or short write-up of one product you took to market from early stage: who bought it, how you found them, what you changed along the way, and the result. No confidential information.Written answer

From Bolder Apps's apply page, checked 2 Nov 2026.

About Bolder Apps

A Miami agency that designs and builds mobile apps, web apps and AI software for startups and established companies at a fixed budget.

Pay schedule: Compensation is not stated in either posting; the startup GTM role adds founding equity.

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