Senior Manager, GTM Enablement

📋 Description

• Design and deliver full-lifecycle enablement programs across Sales, CS, and 24/7 Support.
• Lead and develop a two-person enablement team; mentor and raise the bar.
• Define repeatable GTM playbooks and program cadences; partner cross-functionally.
• Own release readiness and training deliverables for each release tier.
• Build GTM coaching and QA programs; leverage Gong and auto-QA tooling.
• Create live and asynchronous training experiences reflecting real work.

🎯 Requirements

• 10+ years in GTM enablement/L&D; 4+ years leading teams.
• SaaS environment experience with Sales and Customer Success motions.
• Proven track record building full-lifecycle enablement with measurable outcomes.
• Strong command of enablement tech (Gong, Seismic, Lessonly, LMS) and instructional design.
• Excellent written and verbal communication; comfortable presenting to senior leaders.
• Builder’s mindset: prototype, iterate, and move forward without permission.

🎁 Benefits

• Autonomy to shape Calendly's enablement at scale.
• Work with a lean, high-impact team in a fast-paced environment.
• Equity awards, Top Performer Bonus, and competitive benefits.
• Cross-functional collaboration with GTM leaders and executives.
• Exposure to AI-native training tools and innovative enablement approaches.