Senior Manager, GTM Enablement

🕒 April 21

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Calendly

WebsiteLinkedInAll Job Openings

501 - 1000 employees

Founded 2013

☁️ SaaS

⚡ Productivity

🏢 Enterprise

💰 $3.5G Series B on 2021-01

SaaS • Productivity • Enterprise

Calendly is a leading scheduling platform, trusted by over 100,000 organizations worldwide, including 86% of Fortune 500 companies. It simplifies the process of scheduling meetings through integrations with Google Calendar, Microsoft Outlook, and other calendar systems. Calendly offers tools for automated meeting reminders, follow-ups, and customizable scheduling options, making it suitable for individual users and enterprise organizations alike. With features like video conferencing tool integration, custom event types, and comprehensive admin management, it supports a seamless scheduling experience and boosts productivity across teams. Calendly’s platform integrates with over 70 other tools to enhance workflow efficiencies, offering solutions for individuals, teams, and enterprise-level clients.

📋 Description

• 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

• 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

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