Director, GTM Enablement (Remote)

The Director, GTM Enablement is a hands-on leader who builds the skills, content, and tools our sales, retention, and client-facing teams need to win and keep business. This role owns the enablement engine; onboarding, ongoing training, solution-selling methodology, playbooks, and the technology that delivers it, and is responsible for making that engine feel modern, engaging, and genuinely useful rather than a compliance exercise.

The right person understands solution selling and what good looks like in front of a client and is excited to use AI and automation to create training and content that meets people how they learn — not a one-size-fits-all approach. People absorb skills differently, and this role is responsible for delivering enablement in the formats and moments that actually work for each audience.

This role covers enablement across the full GTM organization — inside and field sales, BDRs, presales/solution specialists, Client Care, Retention, and CSM — not sales alone. You'll partner closely with those teams plus Marketing and Product to translate our go-to-market priorities into practical enablement that shows up in behavior and results: win rates, ramp time, save rate, and NPS.

We expect enablement to prove its ROI. This role is accountable for showing the business impact of the training and experience it builds — tying programs to measurable gains in ramp time, quota attainment, save/retention rates, and deal velocity — not just completion rates and satisfaction scores.

• Design and run enablement programs — onboarding, ongoing skill development, and solution-selling methodology — that build confidence and competence across sales (inside and field), BDRs, presales, Client Care, Retention, and CSM, across our core services and new offerings.
• Build training content and learning experiences that are genuinely engaging: scenario-based practice, role-play and call simulations, microlearning, and interactive formats — not slide decks nobody reopens.
• Use AI and automation to modernize how we build and deliver enablement: AI-assisted content creation, coaching and call-review tools, automated content updates, and smarter ways to get the right information to the right person at the right time.
• Own the enablement tech stack (e.g., LMS/content platform, CRM-linked playbooks, Zoom/Zoom Chorus call intelligence, presentation and RFP toolkits) and keep it useful, current, and adopted — not just implemented.
• Partner with sales, retention, and CSM leadership to identify skill and knowledge gaps, then build the training and tools to close them.
• Develop and maintain playbooks, battle cards, and objection-handling guides that reflect how deals are actually won and accounts are actually saved.
• Support new product and service launches with the training, messaging, and readiness plans GTM teams need to sell confidently on day one.
• Own the ROI story for enablement — define and track the metrics that prove training and experience are driving results (adoption, ramp time to productivity, quota attainment, win rates, and retention/save-rate impact) and adjust programs based on the data.
• Coach, guide, and develop enablement team members and cross-functional contributors; act as a change agent who brings people along rather than just publishing content.

• Experience in records/information management, document management, or a related B2B services industry.
• Familiarity with Salesforce, Zoom/Zoom Chorus, or similar GTM/CS and call-intelligence tech.
• Instructional design, adult learning, or video/content production experience.

• Competitive base pay + annual bonus opportunity
• Fully remote opportunity with equipment included
• Medical, Dental, Vision, Disability, and Life insurance
• Self-Managed PTO, 8 paid holidays, paid maternity and parental leave benefits
• 401(k)Retirement plan with 3% company match
• Training and growth opportunities