Head of Sales Enablement

Outtake

$120K — $180K *
Business Services
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 5+ years in sales enablement, sales operations, or a related B2B role
  • Experience building a structured AE onboarding program with measurable outcomes
  • Capability to simplify complex products into field-friendly materials quickly
  • Fluency in MEDDPICC methodology with coaching experience
  • Background in fast-paced, high-growth environments, focusing on building from scratch
  • Comfortable using AI tools for effective enablement
  • Problem-solving mindset to create unique solutions if tools don't exist.

Responsibilities

  • Own the complete sales readiness lifecycle from onboarding to ongoing enablement
  • Maintain and update the AE Sales Playbook and related materials
  • Create AI-powered workflows to enhance rep productivity and deal speed
  • Collaborate with Product Marketing to swiftly translate new messaging into field-ready content
  • Define and track key enablement metrics
  • Engage with Sales, Marketing, and Product teams as an equal contributor, influencing go-to-market strategies.

Benefits

  • 100% company-paid medical, dental, and vision insurance
  • Flexible PTO policy empowering self-management of time off
  • In-person collaboration in a modern waterfront office in Brooklyn
  • Regular company retreats and events to foster team culture.
Full Job Description
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
  • 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. 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.

Similar Jobs

More Jobs at Outtake

  • Software Engineer (Front End)
    $120K — $150K *
    New York, NY 10025 (New York County)
    Consumer Technology
    In-Person
  • Account Executive
    $100K — $150K *
    San Francisco, CA 94112 (San Francisco County)
    Enterprise Technology
    In-Person
  • Account Executive
    $90K — $130K *
    Chicago, IL 60629 (Cook County)
    Enterprise Technology
    In-Person
  • Account Executive
    $80K — $120K *
    Atlanta, GA 30349 (Fulton County)
    Enterprise Technology
    In-Person
  • Account Executive
    $80K — $120K *
    Dallas, TX 75217 (Dallas County)
    Enterprise Technology
    In-Person

More Business Services Jobs

Find similar Head of Sales Enablement jobs: