GTM Architect

Freehand Inc.; United States; Hybrid; USD 120,000 - 180,000; Full time

Benefits offered by this job

Take what you need Vacation Policy

Full health coverage

Life Insurance and Disability benefits

HSA/FSA Access

401(k) with a 4% Employer Match

Fully-paid Parental Leave

Job summary

Freehand is a Series C company with ~100 people across the US and India, enabling AI-driven go-to-market. As our first GTM Architect, you’ll build from scratch—playbooks, collateral, training, and systems—working with the Founder CEO, CRO and sellers to scale.

We are remote and travel-first, with global teams; monthly home internet costs are covered and quarterly fully-paid trips to Office Hubs are arranged to meet cross-functional teams.

Qualifications

• 3–5 years in field/revenue/sales enablement at a B2B SaaS company.
• Built end-to-end seller training programs.
• Created sales collateral that teams actually use.
• Wrote GTM narratives: ICP, value prop, competitive position.
• Native AI user with strong drafting and research skills.
• Ability to spot market adjacencies and new segments.
• Credible with sellers from hands-on experience.

Responsibilities

• Design and own seller onboarding, training programs, and certification frameworks
• Create and maintain sales collateral: decks, one-pagers, battle cards
• Develop GTM narratives for new segments, verticals, and use cases
• Build enablement tooling and AI-powered content systems
• Define leading indicators linking enablement to pipeline and revenue

Skills

Sales Enablement

AI fluency

GTM storytelling

Collateral development

Training program design

Cross-functional collaboration

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: 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 elevate 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 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.