Job description

About Freehand Most AI companies are building tools. We're building the worker. Freehand's AI agents replace the human decision-making and coordination layer that sits above enterprise software — handling the analysis, negotiation, prioritization, and execution that previously required armies of logisticians / supply chain professionals. Our customers include Apple, Meta, GE, Pfizer, J&J, Schlumberger, Cardinal Health, and Unilever. They chose us because we have a fundamentally different answer to what enterprise software looks like when AI can do the job. If you want to work on something that matters, with people who will push you to be sharper than you thought you could be, this is the place. The Role & The Team As our first GTM Architect (aka Sales / Revenue Enablement) hire, you'll build the function from scratch — the playbook, the collateral, the training, the systems. You'll work shoulder-to-shoulder with our Founder CEO, CRO and sellers to understand what's winning, then turn that into infrastructure that scales. This is a commercial role - we want someone who thinks like a seller, uses AI as a reflex, and has opinions on where our next market segment is. What you'll own: - Seller onboarding, training programs, and certification frameworks - Sales collateral including decks, one-pagers, battle cards, objection guides - GTM narratives for new segments, verticals, and use cases - Enablement tooling and content systems, built with AI where it removes friction - Leading indicators that tie enablement activity to pipeline and revenue Who You Are 5+ years in field/ revenue/ sales enablement, ideally at an early-stage B2B AI or SaaS company. You've built from a blank page before and you're energized by it. - Designed, own and run seller training programs end-to-end - Built collateral field teams actually use — you know why most decks fall short - Written GTM narratives: ICP, value prop, competitive positioning, the pitch itself - Native AI user — it's in how you draft, research, build, and find leverage - Thinks at the market level: spots adjacencies, new segments, brings ideas forward - Has genuine credibility with sellers, earned from time working alongside them Working at Freehand Series B, ~100 people across the US and India. Big enough to have infrastructure, small enough that your work is visible. We run on five core operating principles; these are not values-on-a-wall, this is the exact philosophy we built our AI agents on : - Context Before Confidence. We get in, ask (a ton of) questions, connect the dots ourselves and move fast. No passengers, no hand-holding. The amount of confidence you'll have in Week 1 is directly proportional to the context strive to gain. - Decisions, not Recommendations. Freehand folks decide, they don't present options. You'll have real autonomy, and real accountability to match. - High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed. That's the contract. - Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover. Just fix it. - The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters — and can only be done by you. It's a small world. Freehand employees Work Anywhere across the globe (we're remote & travel-first). We also cover your monthly home-internet costs. Every quarter, we arrange for a fully-paid trip to one of our Office Hubs to meet & interact with cross-functional teams. In addition, we proudly offer the following Benefits to all our full-time employees: - Take what you need Vacation Policy - Monthly home-internet costs - Full health coverage (with multiple gold-standard carriers across medical, dental & vision) - Life Insurance and Disability benefits - HSA/FSA Access - 401(k) with a 4% Employer Match - Fully-paid Parental Leave Equal Opportunity Freehand hires on merit — your thinking, your track record, your potential — without regard to race, gender, age, religion, sexual orientation, national origin, disability, or any other protected characteristic. If you meet most of the criteria above but not all of it, apply anyway. We care more about your willingness to learn & take initiative than whether your resume maps perfectly to every line.

Requirements

Must-haves

Seller onboarding, training programs, and certification frameworks
Sales collateral including decks, one-pagers, battle cards, objection guides
GTM narratives for new segments, verticals, and use cases
Enablement tooling and content systems, built with AI where it removes friction
Leading indicators that tie enablement activity to pipeline and revenue
5+ years in field/ revenue/ sales enablement, ideally at an early-stage B2B AI or SaaS company. You've built from a blank page before and you're energized by it.
Designed, own and run seller training programs end-to-end
Built collateral field teams actually use — you know why most decks fall short
Written GTM narratives: ICP, value prop, competitive positioning, the pitch itself
Native AI user — it's in how you draft, research, build, and find leverage
Thinks at the market level: spots adjacencies, new segments, brings ideas forward
Has genuine credibility with sellers, earned from time working alongside them
Working at Freehand
Decisions, not Recommendations. Freehand folks decide, they don't present options. You'll have real autonomy, and real accountability to match.
High Agency, High Trust. We won't manage you closely or ask you to escalate every call. Act, share your reasoning, and course-correct when needed. That's the contract.
Accountability is the Product. When something goes wrong — and it will — we name it, learn from it, and move on. No politics, no cover. Just fix it.
The Work That Remains is the Work That Matters. We actively cut low-value work. What lands on your plate is there because it matters — and can only be done by you.
In addition, we proudly offer the following Benefits to all our full-time employees:
Take what you need Vacation Policy
Monthly home-internet costs
HSA/FSA Access

Nice-to-haves

None flagged.

Application prep

Use the role’s language and application details while tailoring your materials.

Keywords to mirror

Platform: ashby
Effort: quick

Benefits

Benefits detected in the listing.

Dental

Vision

401(K)

Parental Leave