Senior Manager, GTM Enablement

Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey.

Ready to make a serious impact? Millions of people already rely on Calendly, and we’re still in the midst of exciting product growth — it’s a fantastic time to join us. Everything you’ll work on here will accelerate your career to the next level. If you want to learn, grow, and do the best work of your life alongside the best people you’ve ever worked with, then we hope you’ll consider allowing Calendly to be a part of your professional journey. 

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.

What’s so great about working on Calendly’s GTM Operations Team team? 

We are a lean, high-impact team that moves fast and takes pride in building things that actually work. You’ll have the autonomy to shape how enablement runs at Calendly, with the support of a team and leadership who value your expertise.

Why do we need you? We’re looking for someone who brings a builder’s instinct, a systems mindset, and genuine passion for developing people to own end-to-end enablement across Sales, Customer Success, and our 24/7 Support organization.

On a typical day, you will: 

• 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 own a Support QA program (with a focus on auto-QA) and a Sales coaching program leveraging tools like Gong
• 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

• 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

• 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

This role may require occasional travel for company events, team collaboration, or offsites.