Head of GTM Enablement

About Upwind

Upwind is a next-generation Cloud Security Platform that leverages runtime context to identify and prioritize critical risks, providing precise insights and efficient cloud security management. Unlike traditional tools, Upwind uses runtime data proactively for risk prioritization and posture insights, ensuring teams focus on what truly matters. With industry-leading efficiency and eBPF-powered sensors, Upwind delivers comprehensive capabilities, including agentless cloud posture discovery, real-time threat protection, and integrated API security. From misconfigurations to malware defense, Upwind ensures end-to-end, cost-effective cloud infrastructure protection. At Upwind, you'll have the opportunity to think creatively, explore new ideas, and use your skills to make a meaningful impact on our growth.

About The Role

Upwind is scaling a land-and-expand security business, CNAPP and CDR sold to security and DevOps buyers, won in technical evaluations and grown across the customer base over time. We have the strategy and the product. What we need now is someone to build the how: the playbooks, POV motions, and coaching systems that turn strategy into reps who close and expand faster.

This is Upwind's first GTM Enablement hire. You'll start hands-on and close to the work, owning the roadmap end to end, then grow the function as the team scales. You'll partner closely with RevOps and report to our Chief Business Officer, working across Sales, Sales Engineering, Customer Success, and Product Marketing so every GTM team member, wherever they sit in the org, has what they need to win and grow a deal.

What You’ll Do:

• Translate upcoming shifts in product, ICP, and competitive landscape from Product, Marketing, RevOps, CS, and Leadership into rep-ready talk tracks, discovery guides, and value narratives.
• Build enablement across the full GTM motion, not just new logos: discovery, multi-threading, and ROI modeling for AEs and SDRs; the 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, along with a 30-60-90 onboarding program that shortens ramp time for AEs, SDRs, and SAs.
• Run recurring enablement sessions on objection handling, multi-threading, competitive positioning, and closing.
• Equip managers with the frameworks and data they need for high-impact 1:1s and pipeline reviews, and build feedback loops from the field that keep materials current.
• Maintain and extend competitive battlecards for the CNAPP/CDR landscape and keep the analyst narrative in reps' hands.
• Drive real adoption of the GTM stack, including Salesforce, Clari, and Slack, and track leading indicators like certification completion, pitch consistency, and POV quality against lagging indicators tied to new ACV, win rate, and NRR/expansion.

What The First 90 Days Could Look Like:

• Days 1-30: Align with RevOps on deal-stage definitions and a metrics baseline, then shadow live land-and-expand deals to learn the motion firsthand.
• Days 31-60: Ship version one of onboarding along with the first battlecards and POV guide.
• Days 61-90: Launch the first enablement sessions, set a ramp-time target against the baseline, and begin measuring against it.

What We’re Looking For:

• 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. 
• You have hands-on experience building programs from the ground up, with limited resources and no existing infrastructure to lean on. 
• Security or technical infrastructure experience is a plus.
• 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: you can find where a funnel is leaking and build the fix, and you think about enablement in terms of moving a number, not filling a calendar.
• Comfort with a technical security sale and the POV motion, or the ability to get there quickly.
• Executive-ready communication and the ability to turn a messy operational picture into something a VP can act on immediately.

Strong Candidates May Have:

• Experience mentoring teammates, raising the bar for people around them, or leading cross-functional initiatives without formal authority. People naturally look to you when work needs organizing.
• 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.

Apply for this position

Upwind is an equal opportunity employer and does not discriminate on the basis of race, color, religion, sex, sexual orientation, gender identity or expression, national origin, age, disability, veteran status, marital status, pregnancy, genetic information, citizenship status, or any other characteristic protected by applicable law. Applicants with disabilities may also request reasonable accommodation at any stage of the hiring process.

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