VP of Revenue Enablement

About the Role

The VP of Revenue Enablement is a new, dedicated leadership role for Parachute's Enablement function, reporting to the EVP of Revenue Operations as a peer to the leaders of Revenue Operations, Revenue Systems, and Data Analysis.

You'll take over Parachute's existing Enablement team and the programs already in flight, and build from there into a durable, well-resourced function with a clear operating model and a real seat in how Parachute plans and runs go-to-market. You'll have latitude to shape the team as the function matures.

This role exists to grow the business: build a team of effective, efficient sellers and sales leaders, and put in place the training, content, coaching, and tools that make every seller and partner productive faster. Revenue Enablement sits inside Revenue Operations and plugs directly into how Parachute sells — our BDR and AE teams across all four sales motions (Supplier, Health System, Clinician Activation, and Payor), the external supplier reps who sell Parachute on our behalf, our Customer Success and Account Management teams, and the Marketing and Product Marketing functions that support them.

What You'll Do

Build and lead the team

• Directly manage and develop Parachute's Enablement Directors, building the operating rhythm, goals, and career growth this function hasn't had until now.
• Hire, onboard, and develop future enablement team members as the function scales alongside the broader go-to-market org.
• Set the standard for enablement excellence at Parachute — coach your own team the way you expect them to coach sellers and sales leaders.

Own the enablement program

• Take ownership of the pillars defined in Parachute's Enablement Program, turning each from a design document into a living, resourced program across all four core sales motions — Supplier, Health System, Clinician Activation, and Payor.
• Own new-hire onboarding and ramp across our internal seller-facing roles, BDR and AE, with the explicit goal of cutting time-to-first-deal and time-to-quota.
• Own seller productivity as an ongoing metric, not just a ramp-period concern: activity quality, pipeline generation, and quota attainment by rep, team, and motion.
• Drive rep-side HubSpot adoption — the habits, hygiene, and consistent usage across our sales motions that make pipeline data something the rest of the business can trust.
• Build and maintain the playbooks that run our day-to-day motion, including the Lead Attack speed-to-lead playbooks.

Enable partners and the channel

• Own the SSR (Supplier Sales Rep) program — external supplier reps who sell Parachute on our behalf, with their own curriculum, certification, and materials built for that audience rather than repurposed from internal training.
• Build a dedicated Channel Enablement track for the wider partner ecosystem, so partners represent Parachute accurately and consistently.
• Measure partner-sourced activity and productivity with the same rigor applied to our own sellers.

Build the content and certification system

• Build a content architecture that gets sellers and partners the right asset at the right moment, replacing one-off requests and tribal knowledge with a real system.
• Design certification programs for every seller-facing role, not just new hires, so skill and product knowledge stay current as Parachute's platform evolves.
• Partner with Product Marketing, Product, and Revenue Operations to keep messaging, positioning, and talk tracks current as the platform and market evolve.

Coach performance, not just training

• Run a regular cadence of call reviews, deal coaching, and skill-building grounded in real pipeline and real calls, not generic curriculum.
• Train the trainers: build frontline sales leaders' own coaching ability, and coach sales leaders directly, so reinforcement happens inside the sales org and doesn't rely solely on Enablement.
• Partner with Sales and Customer Success leadership to diagnose skill gaps by rep, team, and motion, then build targeted programs to close them.
• Use Gong and pipeline data to find what's actually working in the field and turn it into repeatable coaching.

Partner and measure

• Partner with Revenue Operations, Revenue Systems, and Data Analytics, alongside Sales leadership across all four motions, Customer Success, Marketing, and Product, to translate strategy and roadmap into field-ready execution.
• Build and manage the KPI framework for both the Enablement team's own performance (ramp time, certification completion, content usage) and the sales teams you support (quota attainment, win rate, pipeline conversion), so enablement's impact is measured rather than assumed.
• Represent Enablement in Parachute's planning cycles, bringing a seller's-eye view to decisions made elsewhere in the business.

What We're Looking For

Experience

• 10+ years in revenue enablement, sales training, or a related revenue leadership role, including 5+ years leading teams.
• A track record of building or meaningfully scaling an enablement function, not just running one that was already fully built.
• Experience supporting multiple sales motions or segments (for example enterprise, mid-market, channel or partner); healthcare or other complex B2B2C environments are a plus.
• Experience enabling partners or a channel who sell on your behalf, not only direct employees.
• Bachelor's degree in a related field, or equivalent experience.

Technical Skills

• Hands-on experience with a CRM (HubSpot preferred), a content or enablement platform, and conversation intelligence tools (Gong or similar).
• Comfort building and reading reporting on ramp time, content usage, and rep performance — enough to know when a number is actually telling you something.
• Experience designing curriculum, certification programs, and coaching frameworks from scratch.

How You Work

• Builds durable systems, not one-off decks — sellers and partners find the right content or coaching without opening a ticket.
• Coaches with data, not anecdotes, and delivers a hard truth to a seller or a sales leader when the numbers call for it.
• Leads and scales a team with equal comfort in strategy and execution, as ready to build the curriculum as to sit in on the live call.
• Executive presence: credible in front of sales leadership and the executive team, and equally credible on the sales floor.
• Partners naturally across Sales, Marketing, Product, and Revenue Operations, and knows when to build something new versus adapt what already exists.
• Brings structure to ambiguity and moves with urgency, without cutting corners.

Benefits

• Medical, Dental, and Vision Coverage: Comprehensive plans with options for low-to-no-cost premiums.
• Employer HSA Contribution: Company-funded contributions to your Health Savings Account.
• 401(k) Retirement Plan
• Equity Incentive Plan
• Remote-First Culture: We are remote-first with a dedicated NYC office and reimbursement options for co-working spaces.
• Flexible Vacation Policy
• Summer Fridays: 5 additional Fridays off during the summer (separate from PTO).
• Home Office and Wellness Stipend
• Monthly Internet Stipend
• Annual Learning and Development Stipend
• Annual Company-Wide Bonus: Opportunity for a bonus based on company performance (VP-level target to be confirmed with Total Rewards).

Base Salary Band (based on experience and level)

$200,000–$255,000