Head of GTM (AI Agents)

Bolder Apps; United States; Remote; USD 150,000 - 230,000; Full time

Benefits offered by this job

Founding equity

Remote-friendly (US)

Job summary

Bolder Apps is seeking a Head of GTM for an AI coworker startup. You will own the story, run early sales, and build the engine for the next hundred customers. This is a founding, hands-on role with remote-friendly work across the US.

You will define positioning, ICP, pricing, and a scalable GTM process while partnering with the founder and engineers. The role eventually leads a GTM team as the company grows.

Qualifications

• Must have shipped a B2B software product from zero to revenue.
• Experience selling to technical teams and designers.
• Founded startups or led GTM for early-stage companies is a plus.

Responsibilities

• Own positioning and messaging; define who the product is for and how we say it.
• Define ICP and validate it with real conversations and data.
• Run pricing and packaging experiments; learn what buyers pay for.
• Build outbound from scratch: lists, sequences, initial calls, founder handoff.
• Land first design partners and convert them into paying customers and references.
• Close the first real revenue yourself.
• Stand up a demand-gen and content engine; launches, writing, and demos.
• Collaborate with founder and engineers; feed customer input back into product.
• Set up a simple GTM stack and metrics to track success.
• Hire and lead the GTM team once motion is proven.

Skills

GTM strategy

Pricing strategy

Outbound sales

Content marketing

Positioning & messaging

Customer interviews

AI/tech products

Tools

CRM systems

Marketing automation

Analytics tools

Job description

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.

• 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

• 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