Head of GTM Enablement

Upwind Security•San Francisco, CA

About The Position

Upwind is seeking a Head of GTM Enablement to build the foundational playbooks, POV motions, and coaching systems necessary to accelerate sales and expansion. This is the first GTM Enablement hire, offering the opportunity to own the roadmap end-to-end and grow the function as the team scales. The role involves close collaboration with RevOps, Sales, Sales Engineering, Customer Success, and Product Marketing to ensure all GTM team members have the resources they need to succeed. The ideal candidate will be hands-on, analytical, and comfortable with a technical security sale, with a proven ability to build programs from scratch in a hyper-growth environment.

Requirements

5+ years of experience in GTM/Sales Enablement, or in Revenue/Sales Operations or Sales Engineering with direct experience building enablement programs, training content, or onboarding curricula.
Hands-on experience building programs from the ground up, with limited resources and no existing infrastructure.
A track record of building programs from scratch and staying productive in ambiguity.
The ability to turn a long, meandering briefing into a clear, three-bullet value prop a rep can use the same day.
Analytical rigor: ability to identify funnel leaks, build fixes, and focus enablement on moving numbers.
Comfort with a technical security sale and the POV motion, or the ability to get there quickly.
Executive-ready communication skills.
Ability to turn a messy operational picture into something a VP can act on immediately.

Nice To Haves

Security or technical infrastructure experience.
Experience mentoring teammates, raising the bar for people around them, or leading cross-functional initiatives without formal authority.
Familiarity with land-and-expand or PLG-adjacent GTM motions in a hyper-growth environment.
Direct exposure to competitive cloud security categories like CNAPP or CDR.

Responsibilities

Translate upcoming shifts in product, ICP, and competitive landscape into rep-ready talk tracks, discovery guides, and value narratives.
Build enablement across the full GTM motion, including discovery, multi-threading, and ROI modeling for AEs and SDRs; POV/POC technical-win motion for Sales Engineers; adoption, expansion, and renewal plays for CS; and co-sell enablement for AWS, Azure, and GCP marketplace and channel partners.
Build Upwind's first formal GTM Playbook, covering discovery through ROI, POV, and expansion.
Develop a 30-60-90 onboarding program to shorten ramp time for AEs, SDRs, and SAs.
Run recurring enablement sessions on objection handling, multi-threading, competitive positioning, and closing.
Equip managers with frameworks and data for high-impact 1:1s and pipeline reviews.
Build feedback loops from the field to keep materials current.
Maintain and extend competitive battlecards for the CNAPP/CDR landscape.
Keep the analyst narrative in reps' hands.
Drive adoption of the GTM stack, including Salesforce, Clari, and Slack.
Track leading indicators like certification completion, pitch consistency, and POV quality against lagging indicators tied to new ACV, win rate, and NRR/expansion.