[Hiring] Senior Manager, GTM Enablement @Calendly

Role Description

The GTM Operations team at Calendly is the engine behind how we go to market, building the systems, programs, and capabilities that help our Sales, Customer Success, and Support teams perform at their best. As Senior Manager, GTM Enablement, you’ll lead a small team of two enablement professionals and own the full enablement lifecycle across our Sales, Customer Success, and 24/7 Support organizations. You’ll report directly to the Senior Director, GTM Operations.

This is a role for a builder: someone energized by designing programs that actually move the needle, not just delivering training for training’s sake. You’ll partner closely with GTM leadership, Product Marketing, and Product to ensure our teams are equipped to sell, support, and succeed.

A day in the life of a Senior Manager, GTM Enablement at 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.
• 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.

Qualifications

• 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.

Requirements

• Experience enabling 24/7 support teams, including designing QA programs with auto-QA tooling.
• Hands-on experience building AI-native or AI-assisted training experiences; you’ve prototyped with tools yourself, not just managed a team that did.
• Demonstrated ability to operate credibly with senior GTM leaders and in executive forums.
• Experience setting annual enablement strategy and translating it into a clear operating plan across multiple teams and stakeholders.

Benefits

• Base salary is just one component of Calendly’s total rewards package.
• All full-time (30 hours/week) employees are also eligible for our Top Performer Bonus program (or Sales incentive), equity awards, and competitive benefits.