GTM Architect

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: 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

3–5 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 C, ~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

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 think…