GTM Architect - Enablement & Revenue Playbooks (Remote)

Freehand; Chicago (IL); On-site; USD 140,000 - 190,000; Full time

Benefits offered by this job

Health coverage

401(k) employer match

Fully-paid parental leave

Work Anywhere

Office hub trips

Job summary

Freehand is hiring its first GTM Architect to build the sales enablement function from the ground up. You'll craft the playbook, collateral, training, and systems, working side-by-side with the Founder CEO, CRO, and sellers to translate winning patterns into scalable infrastructure.

You are a builder with 3–5 years in field or revenue enablement, who designs training programs, creates practical collateral, writes GTM narratives, and uses AI to sharpen every move.

Qualifications

• 3–5 years in field/revenue/sales enablement at a B2B AI or SaaS company
• Designed, owned, and run seller training programs end-to-end
• Wrote GTM narratives: ICP, value prop, competitive positioning

Responsibilities

• Build and own seller onboarding programs, training, and certification
• Create sales collateral: decks, one-pagers, battle cards
• Develop GTM narratives for new segments and use cases
• Build enablement tooling and content systems with AI to reduce friction
• Track leading indicators to tie enablement to pipeline and revenue

Skills

Sales enablement

GTM narratives

AI fluency

Market thinking

Seller credibility

Job description

Freehand is hiring its first GTM Architect to build the sales enablement function from the ground up. You'll craft the playbook, collateral, training, and systems, working side-by-side with the Founder CEO, CRO, and sellers to translate winning patterns into scalable infrastructure.

You are a builder with 3–5 years in field or revenue enablement, who designs training programs, creates practical collateral, writes GTM narratives, and uses AI to sharpen every move.