Sales Enablement Lead

About Compa

Compa is a venture-backed AI startup revolutionizing the future of compensation! We're bringing AI-forward tools and human-centered engineering to make pay competitive and fair, for all. By offering a premier, live compensation data platform that delivers top-tier intelligence to enterprise teams, we enable the world's largest companies to make smart and fair decisions while staying competitive and compliant. In dynamic job markets during the rise of AI, companies need the best data to stay competitive!

Our force-multiplying team is powered by live data and thoughtful design, and our products have earned the trust of the world’s largest companies: NVIDIA, Stripe, DoorDash, OpenAI, Moderna, Workday, Ulta, Target, and more.

Come build with us!

The Role

As Enablement Lead, you will build the training program that turns every new and tenured seller into a world-class one: faster ramp, stronger skills, and a shared way of selling.

You will own onboarding, ongoing development, and certification, and build the manager capability that makes it stick. You will partner with sales leaders on a training roadmap for a fast-growing, AI-first go-to-market, and keep raising the bar on what good looks like.

Our product is increasingly AI-driven, including our AI agents layer, so this role is central to making sure every seller can explain that value with fluency and conviction as new capabilities ship. Success shows up in ramp time, win rate, pipeline quality, and forecast accuracy.

What You’ll Do

Onboarding and new-hire ramp

• Own the onboarding plan from day one through full quota, with clear milestones and certification before a rep carries a full number.

• Design curriculum that covers market, competition, company, product, value proposition, sales process, methodology, tools, and skills.

• Deliver through formats that work: online, classroom, peer group, flipped-classroom, and role-play.

• Help run the annual sales kickoff and mid-year summit as training events, not announcements.

Ongoing skills development and certification

• Build a continuous training calendar for Sales, Customer Success and Insights teams: discovery, business case and ROI, multi-threading, security and procurement, negotiation, and expansion.

• Certify sellers on the skills that matter, using role-plays and call-recording reviews as the assessment, not just course completion.

• Teach account planning for the largest enterprise accounts.

• Use pipeline review themes and call reviews to decide what to teach next.

• Leverage AI to deliver ongoing innovation and efficiencies for the organization.

Manager and leader development

• Teach front-line managers to coach: deal inspection, call review, and feedback using a shared scorecard.

• Certify managers on the methodology first, so they can reinforce what reps learn.

• Turn the forecast and pipeline review cadence into ongoing manager training.

Sales methodology

• Own the sales methodology as the one way the team qualifies, advances, and inspects deals, with a clear "why now" for every opportunity.

• Build the methodology into stage exit criteria instead of running it as a separate system. Gate stage advancement on the smallest set of elements that matter, and score the rest without blocking.

• Create an evidence-based deal scorecard for inspection, coaching, and pipeline rollups.

Pipeline management and forecasting

• Teach the pipeline standards: what counts as real pipeline, stage definitions, aging, and CRM hygiene, in partnership with RevOps.

• Teach managers to forecast from deal evidence instead of rep confidence, with clear category definitions and a roll-up cadence.

• Track forecast accuracy by rep, manager, and segment, and turn the gaps into coaching and training.

AI product fluency

• Build and own the training strategy for our AI-driven roadmap, so sellers clearly and confidently articulate the value of the AI agents layer.

• Keep messaging, positioning, and competitive differentiation in training current with Product Marketing and Product as capabilities ship.

• Champion the use of AI-powered selling tools across the sales org, from call analysis and coaching to prospecting and deal intelligence, and partner with RevOps to ensure they're adopted and delivering measurable results.

Playbooks and in-the-moment support

• Leveraging AI to build playbooks, battlecards, and objection handling that reinforce what is taught, and keep them in the flow of work (CRM, chat, conversation intelligence).

• Keep them current and trusted, so a rep finds the answer in seconds, not in a course.

Measuring what works

• Measure program effectiveness through new-hire ramp, certification results, skill assessments, participant and leader feedback, and retention.

Who you'll work with

You report to the Chief Revenue Officer and partner closely with:

• Sales leaders and front-line managers, who reinforce everything you build.

• Revenue operations, on stage definitions, CRM hygiene, and forecast tooling.

• Product marketing, on messaging, battlecards, and launch enablement as new AI capabilities ship.

• Customer success, on handoffs, expansion plays, and renewal playbooks.

• Product, security, and legal, on the technical and compliance answers reps need mid-deal.

What We’re Looking For

Minimum

• Bachelor's degree or equivalent experience.

• 5+ years designing, developing, and delivering sales training, including leading a team or building the function from scratch.

• Experience running onboarding and certification programs that shortened ramp time.

• Working knowledge of MEDDPICC or a similar methodology, with a record of embedding it in stage criteria and coaching, not just teaching it.

As a Plus

• 5+ years in B2B sales, sales leadership, or sales enablement, including software sales.

• Experience building manager coaching programs and designing forecast and pipeline review processes.

• Experience building AI tools to accelerate AE performance

• Ability to build and facilitate online, classroom, peer group, flipped-classroom, and role-play training.

• Fluency with an LMS, HubSpot or a comparable CRM, and conversation intelligence tools, plus comfort using data to decide what to teach.

• Experience selling or enabling complex, multi-stakeholder enterprise deals with security and procurement review.

• A strong facilitator and coach who earns credibility with senior reps and front-line managers.

• Clear, concise writing: you can turn a messy deal into a one-page playbook.

• Sound judgment on what belongs in a program versus what belongs in the flow of work.

Compa offers a competitive and comprehensive benefits package including medical, dental, vision, PTO and parental leave, equity, company offsites, continuous education, commuter benefits and a flexible work environment.