Build the Enablement Engine at a Rapidly Scaling AI Powerhouse

This is not an enablement job. It is an opportunity to build the foundation of enablement at a $1B+ AI company already transforming two of the most essential industries on the planet.

The company has built world-class AI that’s actually being used — in real estate, healthcare, and beyond. With a fully staffed sales team spanning AE, SDR, and CSM roles, they’re now ready to build a high-impact enablement function. You won’t inherit someone else’s playbook. You’ll create the one that scales us into the next phase of growth.

Why This Role Is Different

You are not here to maintain. You are here to architect.

• You will be the second enablement hire in a hyper-growth company with executive buy-in and a clear mandate to scale fast.

• You will own onboarding, product training, coaching, content, and LMS from end to end — across a GTM org of more than 60 reps.

• You will work with a product that reps actually understand and care about. No more enabling on abstract cybersecurity software.

• You will have the headspace and autonomy to build, supported by strong leadership and a fast-moving, mission-driven culture.

What You Will Do

• Fully rebuild and relaunch onboarding for new AEs, SDRs, and CSMs

• Design and execute product enablement for a platform that evolves every week

• Develop scalable training content, playbooks, and certification paths using SkillJar

• Partner cross-functionally with GTM leadership to identify skill gaps and deploy solutions

• Deliver live training, coaching, and workshops that improve performance across roles

• Measure success through productivity, ramp time, and performance metrics — and iterate fast

What We’re Looking For

The must-haves:

• 2–5 years of experience in enablement or a field-facing GTM role (AE, SDR, or CSM)

• B2B SaaS background, ideally in enterprise sales or complex product environments

• Proven experience building enablement programs from scratch

• LMS fluency (SkillJar preferred) and comfort building digital learning programs

• Strong facilitation and presentation skills — you must be comfortable leading live sessions

• A track record of working on lean teams or as a team of one

Extra credit if you:

• Were a high-performing AE or SDR before moving into enablement

• Have experience at Series A–D startups with fast-changing product and GTM motions

• Are energized by autonomy and want to leave your fingerprints on something that lasts

What Success Looks Like

• You reduce ramp time by weeks

• You drive measurable improvement in quota attainment

• You build a scalable system that works for 60 reps now — and 200 reps later

• You are trusted as a business-critical partner by GTM leadership

• You make the sales team better every single month

Compensation & Benefits

• Base salary: 150000 to 190000 dollars

• Equity: Generous stock options in a well-capitalized, Series D company

• Bonus: No commission structure, but discretionary bonuses awarded based on performance and impact

• Insurance & Benefits: Comprehensive health benefits & 401k

Location and Travel

• Hybrid encouraged in New York, Boston, San Francisco, Chicago, or Austin

• Remote open to top candidates willing to travel

• Travel expectation: Monthly to NYC HQ (all expenses covered)

• Onboarding includes 2–3 weeks onsite with reps and leadership

Culture and Pace

This is a high-ownership, high-expectation culture. There is no clock-watching, and no micromanagement. You will be trusted to manage your time and outcomes like a senior operator — and expected to bring intensity, speed, and craft to your work.

If you are looking for a 9 to 5, this is not your role. But if you want to help shape a fast-scaling company from the inside — and be known as the person who built enablement from the ground up — you are in the right place.

Interview Process

• Recruiter screen with talent team

• Hiring manager interview with the Head of Enablement

• Practical case study (build + present live training plan)

• Final round interviews with GTM leadership and CEO exposure

• Offer

You do not need to wait for permission to lead here. If you are ready to architect the systems that accelerate revenue at scale — we would love to meet you.

Apply now or connect directly to start the conversation.