Sr. Director GTM Enablement and Programs

Rightworks offers the only intelligent cloud purpose-built for accounting firms and professionals. Backed by award-winning support, our fully managed IT and applications ensure customers have secure, reliable, on-demand access to their technology. We provide a curated software ecosystem that simplifies the complexity of running an accounting firm or small business, supported by a community of thought leaders, peer networks, and educational resources. Our success is made possible by leveraging decades of specialized experience in leading accounting firms, SMBs and technology companies. Thousands of Firms and SMBs count on us to run their business every day. 

We have a great team, we’re growing fast and have a winning culture based on innovation, teamwork, and mutual respect. 

Job Overview

We are seeking a visionary and results-oriented Senior Director GTM Enablement and Programs to architect and lead a best-in-class enablement function that drives revenue growth, accelerates seller productivity, and strengthens our go-to-market execution. 

This executive-level leader will own the end-to-end enablement strategy across the revenue organization, ensuring alignment between Sales, Marketing, Product, Customer Success, and Revenue Operations. The Senior Director will design scalable programs, systems, and governance frameworks that support onboarding, continuous development, sales process excellence, and deal optimization. 

This is a highly strategic and operational role requiring a leader who can both define long-term enablement vision and execute with precision.

The position is hybrid position.

Responsibilities

Enterprise Enablement Strategy & Leadership 

• Define and execute a multi-year sales enablement vision aligned with corporate strategy and GTM objectives. 

• Individual Contributor role to start. Build scalable function.

• Establish enablement as a measurable revenue driver with clear ROI and executive visibility. 

• Serve as a trusted advisor to executive sales leadership on performance acceleration and capability development. 

Revenue Performance & Productivity Acceleration 

• Design programs that reduce ramp time, increase quota attainment, and improve win rates across segments. 

• Partner with Sales Leadership and Revenue Operations to diagnose performance gaps and deploy targeted enablement interventions. 

• Develop competency frameworks and career pathing for sales roles. 

Training & Onboarding Excellence 

• Architect scalable onboarding programs for all revenue roles. 

• Oversee ongoing training initiatives across product knowledge, industry expertise, sales methodology, negotiation, and leadership development. 

• Institutionalize continuous learning programs that adapt to market and product evolution. 

Content Strategy & Messaging Governance 

• Establish a centralized content strategy that ensures sellers have access to relevant, high-impact materials. 

• Oversee the development of playbooks, battle cards, pitch decks, value frameworks, and case studies in partnership with Marketing and Product. 

• Implement content governance and measurement to drive adoption and effectiveness. 

Sales Tools, Technology & Infrastructure 

• Own the enablement technology stack (CRM, LMS, sales engagement platforms, analytics tools). Seek new vendors in order to scale.

• Identify, evaluate, and onboard new vendors to scale enablement capabilities. 

• Partner with RevOps to ensure systems support pipeline visibility, forecasting accuracy, and seller productivity. 

Sales Process & Methodology Optimization 

• Standardize and reinforce sales methodologies and qualification frameworks. 

• Formalize and scale Deal Desk and Deal Review processes to improve deal velocity, pricing governance, margin optimization, and a build Win-Loss program. 

• Drive inspection rigor and forecasting discipline across the sales organization. 

Strategic Vendor & Program Management 

• Lead executive partnership with PClub (3rd party enablement vendor) to maximize ROI and adoption. 

• Integrate PClub programming into broader enablement initiatives and measure engagement impact on performance. 

Data, Analytics & Executive Reporting 

• Define KPIs to measure enablement effectiveness, including ramp time, win rates, quota attainment, deal cycle length, and content utilization. 

• Deliver regular executive-level reporting with actionable insights. 

• Build a culture of data-driven decision-making within the enablement function. 

Cross-Functional Revenue Alignment 

• Serve as the connective tissue between Sales, Marketing, Product, Customer Success, and Finance. 

• Establish structured feedback loops to ensure field insights influence product roadmap, messaging, and GTM strategy. 

• Partner closely with Finance and RevOps to ensure compensation plans and incentives align with enablement priorities. 

Requirements

• 10+ years of progressive experience in Sales Enablement, Revenue Operations, or Sales Leadership, with 5+ years in senior leadership roles. 

• Proven track record of building and scaling enablement programs in high-growth SaaS or technology organizations. 

• Experience leading cross-functional initiatives at the executive level. 

• Strong analytical acumen with the ability to translate data into strategic action. 

• Demonstrated success in driving measurable improvements in sales productivity and revenue outcomes. 

• Exceptional executive presence, communication skills, and change management capability. 

• Experience in SaaS or a fast-paced B2B tech environment 

• Sales experience or deep empathy for the challenges faced by quota-carrying reps 

Eligibility Requirements

• This role is open to US Citizens or permanent residents authorized to work in the United States. Rightworks LLC is unable to offer visa sponsorship.

• Due to specific state regulations, we are unable to accept applications from residents of California, Hawaii, or Alaska.

• Relocation will not be offered for this position. 

Compensation

Our Compensation range for this role ranges from $215,000 to $230,000 annually plus bonus, and is determined based on factors such as relevant experience, skills, and internal equity. 

Benefits

To provide best-in-class solutions, we need a best-in-class team. We offer competitive salaries to recruit the best talent. We provide company-paid short and long-term disability insurance, life insurance and a generous 401K match. We offer highly affordable medical, dental, vision coverage, and many other valuable benefits. We offer flexible PTO, and numerous paid holidays, affording you the time to be there for what is important in your life. We encourage giving back to our communities by providing paid volunteer time off. We are proud to be an Equal Opportunity Employer! 

This job description may not be inclusive of all assigned duties, responsibilities, or aspects of the job described, and may be amended at any time at the sole discretion of the employer.