Senior Manager, GTM Enablement

New

CalendlySaaS

RemoteFull-TimeManager

Salary173862 - 245452 USD per year

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Job Details

Experience: 10+ years

Requirements

10+ years of experience in GTM enablement, learning & development, or a closely related function
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)
Instructional design best practices
Excellent written and verbal communication skills
Comfortable presenting to and influencing senior leadership
A builder’s mindset
Experience enabling 24/7 support teams, including designing QA programs with auto-QA tooling (preferred)
Hands-on experience building AI-native or AI-assisted training experiences; you’ve prototyped with tools yourself, not just managed a team that did (preferred)
Demonstrated ability to operate credibly with senior GTM leaders and in executive forums (preferred)
Experience setting annual enablement strategy and translating it into a clear operating plan across multiple teams and stakeholders (preferred)

Responsibilities

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

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