Head of Sales Enablement

Outtake exists to empower and facilitate trust for a digital-first world. Today, impersonation, fraud, AI-driven scams, and identity abuse spread faster than any security team can respond to. So we built something different: an agentic AI platform that proactively detects, monitors and takes down impersonators and automates protection in hours, not weeks. Built by ex-Palantir, ex-CTO/founders, and ex-Notion engineers, Outtake is designed for clarity, autonomy, and velocity. Our goal is ambitious: become the trust layer of the modern internet. And we intend to do it with a lean, dense, exceptionally talented team. We are building a reputation as the place where modern, AI-enabled enterprise selling is innovated, taught, and practiced. We have a strong foundation: a structured onboarding program, a living sales playbook, a deal inspection framework, and a certification system that produces ramp-ready AEs. Now we need someone to own it, elevate it, and make it a durable competitive advantage. The Sales Enablement Leader will report directly to the VP of Global Sales and sit at the intersection of sales, marketing, and product. You use AI to enhance your work rather than do your work. You build systems. You love making salespeople better by helping them build real value for customers. And you want to do it 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 — 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 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. Your work directly shapes how Outtake goes to market LIFE AT OUTTAKE Outtake is backed by top-tier investors and operators who believe in our mission and our model: a lean, dense, exceptionally talented team building a category-defining product. With strong financial footing and a long runway, we prioritize creating an environment where people can do the best work of their careers. - Office: We are an in-person team (5 days a week, with flexibility as needed) working out of a stunning waterfront office in Brooklyn. Collaboration, speed, and clarity matter. - Health: 100% company-paid medical, dental, and vision for employees. - Time Away: Flexible PTO. We trust adults to manage energy, not clock time. - Culture & Team: Annual company retreats and regular in-person events.