Head of Sales Enablement

Outtake

Sales Enablement Leader at Outtake empowering sales with AI-driven solutions. Engaging with Sales, Marketing, and Product to optimize sales readiness and effectiveness.

Posted 6/24/2026full-timeNew York City • New York • 🇺🇸 United StatesLeadWebsite

About the role

Key responsibilities & impact

Owning the full lifecycle of sales readiness: From Day 1 onboarding through ongoing field enablement for every AE at Outtake
Keeping the AE Sales Playbook, battle cards, demo scripts, and objection banks current with continual validation of effectiveness.
Building AI-powered workflows that reduce rep prep time, improve call quality, and accelerate deal velocity across the team
Partnering with Product Marketing to translate new messaging and positioning into field-ready content the moment it ships
Defining and tracking enablement metrics
Sitting at the table with Sales, Marketing, and Product as a peer, not a support function. Your work directly shapes how Outtake goes to market

Requirements

What you’ll need

5+ years in sales enablement, sales operations, or a closely related role at a B2B company
Proven track record building or running a structured AE onboarding program with measurable ramp outcomes — not just inheriting one
Ability to take a complex product or concept and turn it into clean, usable field material fast
Deep fluency with MEDDPICC or equivalent methodology, and the ability to coach reps on applying it in live deals
Experience in fast-moving, early-stage or high-growth environments where you built from scratch, not maintained
Genuine comfort with AI tools and a bias toward using them to make enablement more effective and scalable
Willingness to vibecode solutions when a problem needs a tool and one doesn't exist yet

Benefits

Comp & perks

100% company-paid medical, dental, and vision for employees.
Flexible PTO. We trust adults to manage energy, not clock time.
Annual company retreats and regular in-person events.

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

sales enablementsales operationsonboarding program developmentenablement metrics trackingMEDDPICC methodologyAI-powered workflowsfield-ready content creationdeal velocity improvementcall quality enhancementobjection handling

Soft Skills

collaborationcommunicationcoachingproblem-solvingadaptabilitycreativityorganizational skillsleadershipstrategic thinkingtime management