Director, Revenue Enablement

Bring your best and truest self. We celebrate what makes us different and what brings us all together. At Greenway Health, we are committed to an inclusive environment and a culture of belonging as we pursue our purpose of healthier communities, successful providers, and empowered patients. We are united in our goal to build the future of healthcare technology. Join us.

The Director of Revenue Enablement is responsible for defining, building, and executing Greenway’s Revenue Enablement strategy across Sales, Customer Success, and Professional Services.

This leader owns the design and execution of enablement programs that increase commercial effectiveness, accelerate productivity, reinforce execution excellence, and drive measurable revenue impact. The Director of Revenue Enablement serves as a strategic partner to Commercial, Product Marketing, Product, and Revenue Operations leadership — ensuring that revenue-facing teams are equipped with the skills, tools, systems, and reinforcement required to execute consistently and win in-market.

This is a hands-on builder role.

The Director will operate as an “army of one” — responsible for architecting the enablement strategy while personally designing, building, delivering, and optimizing programs and systems. This role requires a high-agency operator who thrives in ownership, moves seamlessly from strategy to execution, and builds scalable foundations for future growth.

The ideal candidate combines commercial acumen, sales methodology expertise, enablement technology fluency, and strong instructional design capabilities with the ability to drive measurable business outcomes.

Key Responsibilities

Define and Execute the Revenue Enablement Strategy

• Develop and own Greenway’s end-to-end Revenue Enablement strategy aligned to business growth objectives.
• Establish measurable impact goals (ramp time, win rates, methodology adoption, tool utilization, deal velocity).
• Build the enablement operating model across Sales, Customer Success, and Professional Services.
• Serve as the strategic enablement partner to Commercial leadership, Product Marketing, RevOps, and Product.

This role requires both strategic vision and direct execution.

Rebuild and Modernize Onboarding & Productivity

• Architect and personally deliver a best-in-class onboarding program that reduces ramp time and improves long-term effectiveness.
• Design structured learning journeys by role, tenure, and segment.
• Establish measurable ramp benchmarks and certification milestones.
• Implement reinforcement and retention strategies grounded in adult learning best practices.
• Continuously optimize onboarding using performance data and field feedback.

Own Enterprise Sales Methodology & Execution Excellence

• Lead adoption, certification, and reinforcement of Greenway’s Value Selling methodology and Discovery Framework.
• Embed methodology into onboarding, Gong scorecards, Accord playbooks, and coaching frameworks.
• Personally facilitate workshops, manager coaching sessions, and reinforcement programs.
• Ensure commercial team members are equipped to execute approved value narratives consistently.

Build and Govern the Revenue Playbook System

• Translate Product Marketing approved messaging, positioning, and value frameworks into scalable execution tools.
• Design and maintain high-impact playbooks, pitch decks, scripts, and buyer-facing materials.
• Establish content lifecycle governance (versioning, approval alignment, usage tracking).
• Own and manage the SE Gallery and SharePoint enablement ecosystem.
• Continuously improve usability, clarity, and adoption of revenue content assets.

Lead Revenue Enablement Technology & AI Optimization

• Partner with RevOps on strategy, configuration, governance, and optimization of revenue enablement tools, including Gong, Accord, and Sales Assistant AI.
• Architect Gong trackers, scorecards, briefs, themes, and Engage Flows to reinforce execution standards.
• Build and manage playbooks and buyer enablement workflows within Accord.
• Govern AI-assisted content usage to ensure alignment with approved messaging and claims.
• Drive adoption, education, and measurable ROI from enablement platforms.

Institutionalize Certification & Continuous Development

• Design and operate structured product, process, and methodology certification programs.
• Partner with L&D to create, publish, and track learning within Articulate, and related systems.
• Implement ongoing skill development and reinforcement cadences tied to business priorities.
• Establish clear expectations and accountability for certification compliance.

Elevate National Sales Meetings & Commercial Events

• Own enablement strategy and hands-on execution for Sales Kickoff (IGNITE) and key commercial meetings.
• Design performance-focused agendas tied to measurable outcomes.
• Develop training content and personally facilitate key sessions.
• Partner cross-functionally to ensure strong narrative alignment and post-event reinforcement.

Build a Data-Driven Enablement Intelligence Function

• Establish KPIs and dashboards linking enablement programs to revenue outcomes.
• Leverage Salesforce, Gong, and related systems to identify skill gaps and execution challenges.
• Conduct structured needs assessments and implement targeted interventions.
• Provide actionable insights to Commercial leadership and Product Marketing to inform execution refinement.

Lay the Foundation for Future Scale

• Design systems, documentation, and governance frameworks that can scale as the organization grows.
• Establish repeatable program templates and processes.
• Develop a roadmap for future enablement team expansion.

Required Experience & Qualifications

• 10+ years of experience in Revenue Enablement, Sales Leadership, Commercial Operations, or a related revenue-facing role within a high-growth or complex B2B environment.
• Proven track record of building or modernizing enablement functions and driving measurable commercial performance improvements.
• Demonstrated impact on time-to-productivity, win rates, methodology adoption, or deal execution quality.
• Deep expertise in implementing and scaling formal sales methodologies (e.g., Value Selling, Challenger, MEDDICC, SPIN, Sandler, etc.).
• Strong hands-on experience configuring and optimizing revenue enablement tools such as Gong, Accord, sales engagement platforms, LMS systems, and AI-assisted selling tools.
• Experience designing onboarding programs, certification frameworks, and reinforcement models grounded in adult learning principles.
• Exceptional communication and executive presence with the ability to influence senior stakeholders.
• Strong analytical capabilities and ability to leverage data to inform enablement strategy and demonstrate impact.
• High agency and comfort operating independently without a supporting team.

Preferred Qualifications

• Experience in healthcare, SaaS, or complex solution-based selling environments.
• Experience supporting multi-role revenue teams (Sales, CS, PS).
• Experience leading national sales meetings or enterprise-wide commercial initiatives.
• Advanced degree or professional certifications in sales methodology or instructional design.

What Success Looks Like in This Role

• Redesigned and rebuilt Revenue Enablement function, supporting the entire GTM team
• Reduced ramp time for new hires.
• Improved sales methodology adherence and execution consistency.
• Increased adoption and measurable ROI from Gong, Accord, and AI tools.
• Strong cross-functional alignment across Product Marketing, RevOps, and Commercial teams.
• Scalable enablement systems positioned for future team growth.

Work Environment/Physical Demands 

• While at work, this position is primarily a sedentary job and requires that the associate can work in an environment where they will consistently be seated for most of the workday 
• This role requires that one can sit and regularly type on a keyboard most of their workday 
• This position requires the ability to observe a computer screen for extended periods of time to observe their own and others’ work, as well as in-coming and out-going communications via the computer and/ or mobile devices. 
• The role necessitates the ability to listen and speak clearly to customers and other associates           

Here’s what we can offer you in exchange for your amazing work: 

• Competitive pay
• Medical, dental and vision benefits
• Matching 401(k) 
• Generous paid time-off programs
• Education reimbursement
• Growth potential for your career
• Corporate discounts

At Greenway, we strive to imagine, empower, engage, and inspire. Join us!

To learn more about Greenway, take a video tour of our office, and meet our employees, visit us at www.GreenwayHealth.com/careers.

Disclaimer: This Job Summary indicates the general nature and level of work expected of the incumbent(s). It is not designed to cover or contain a comprehensive listing of activities, duties or responsibilities required of the incumbent. Incumbent(s) may be asked to perform other duties as requested. Greenway Health, LLC is an Equal Opportunity Employer. We do not discriminate on the basis of race, religion, age, gender, national origin, sexual orientation, disability, or veteran status.  

While this position is primarily remote, please note that if you reside within a 26-mile radius of our corporate office, you will be required to work in a hybrid capacity. This means you will be expected to work on-site at the corporate office for part of the week and remotely for the remainder. This hybrid arrangement is designed to foster team collaboration and engagement. Our corporate office is located at 4301 Boy Scout Blvd, Tampa, FL 33607. Please consider your proximity to this location when applying. 

If you are a resident of a state that requires pay transparency, please email us at [email protected] to receive compensation and benefits information for this role. Be sure to include the Job ID in the subject line of your email.