Senior Manager, GTM Enablement

Calendly

. Design and deliver full-lifecycle enablement programs (onboarding, product training, skill-building, and ongoing process training) across our Sales & Customer Success and 24/7 Support organizations .

Posted 4/21/2026full-timeRemote • 🇺🇸 United StatesSenior💰 $173,862 - $245,452 per yearWebsite

About the role

Key responsibilities & impact

Design and deliver full-lifecycle enablement programs (onboarding, product training, skill-building, and ongoing process training) across our Sales & Customer Success and 24/7 Support organizations
Lead and develop your team of two as a player-coach, building and delivering programs yourself while delegating, mentoring, and raising the bar for the team
Define repeatable operating playbooks and program cadences for GTM initiatives (launches, operational changes, vertical programs), partnering cross-functionally with Sales, Support, Product Marketing, GTM Ops, and Product
Own release and launch readiness for all customer-facing teams, defining the activities, workflows, and deliverables (trainings, documentation, etc.) tied to each release tier and playbook, in partnership with Product and Product Marketing
Own and build out Calendly's GTM coaching and quality programs — including a Sales coaching program leveraging tools like Gong and a Support QA program with a focus on auto-QA
Build and maintain a mix of live and asynchronous training experiences, including hands-on, demo-based formats that reflect how our teams actually work
Build AI-native enablement experiences that help our teams learn and apply skills faster
Define and track measurable impact metrics for all enablement programs, connecting training to business outcomes
Partner with GTM managers and senior leaders to identify skill gaps and design targeted 1:1 training support for individuals who need additional development

Requirements

What you’ll need

10+ years of experience in GTM enablement, learning & development, or a closely related function, with at least 4 years managing a team
Experience in a SaaS environment with a strong understanding of Sales and Customer Success motions
Proven track record building full-lifecycle enablement programs with measurable, data-driven outcomes
Strong command of enablement technology (e.g., Gong, Seismic, Lessonly, LMS platforms, QA tools) and instructional design best practices
Excellent written and verbal communication skills; comfortable presenting to and influencing senior leadership
A builder’s mindset: you prototype, iterate, and define the path forward without waiting for permission.

Benefits

Comp & perks

All full-time (30 hours/week) employees are also eligible for our Top Performer Bonus program (or Sales incentive)
equity awards
competitive benefits

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

GTM enablementlearning & developmentenablement programsinstructional designdata-driven outcomesmeasurable impact metricscoachingskill-buildingprocess trainingteam management

Soft Skills

leadershipmentoringcommunicationinfluencingcollaborationproblem-solvingadaptabilitycreativityprototypingiteration