Head of Sales Enablement

About the role

The Sales Enablement Leader will report directly to the VP of Global Sales and sit at the intersection of sales, marketing, and product. You will use AI to enhance your work rather than do your work. You will build systems and love making salespeople better by helping them build real value for customers. This role is at a company with category-defining technology and serious growth ambition.

What You'll Need To Bring

• 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
• 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

What You'll Achieve

• 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

Life at Outtake

• Office: For those in NY, we are an in-person team (5 days a week, with flexibility as needed) working out of a stunning waterfront office in Brooklyn.
• Culture & Team: Annual company retreats and regular in-person events.

Equal Opportunity Employer

We are committed to building a diverse, inclusive team.