Senior GTM Project Manager, Strategy & Operations

Summary

Join Calendly's GTM Operations team as a Senior GTM Project Manager, Strategy and Operations, reporting to the Senior Director of GTM Operations. You will drive strategic planning, operational rhythms, OKR management, and special projects across sales, customer success, marketing, and customer experience. A typical day involves driving GTM strategic planning and OKR management, establishing and owning the rhythm of the GTM business, building and maintaining dashboards and reporting tools, optimizing workflows, leading high-impact special projects, supporting change management, and serving as a trusted advisor to GTM leaders. This role requires 6–9 years of experience in go-to-market operations, project management, or strategy in a fast-paced tech environment, a proven track record of driving strategic planning and managing OKRs, exceptional project management skills, strong analytical skills, strong Jira and Asana management skills, excellent communication and presentation skills, and the ability to navigate ambiguity. The position offers the opportunity to make a serious impact and accelerate your career within a growing company.

Requirements

• 6–9 years of experience in go-to-market operations, project management, or strategy in a fast-paced tech environment
• Proven track record of driving strategic planning and managing OKRs with measurable business outcomes
• Exceptional project management skills, including process improvement, operational excellence, and strong budgetary discipline
• Strong analytical skills with hands-on experience in dash-boarding and reporting tools
• Strong Jira and Asana management skills, including admin-level capabilities to configure workflows, manage permissions, and oversee work tracking
• Excellent communication and presentation skills, with demonstrated ability to influence cross-functional teams and executive stakeholders
• Ability to navigate ambiguity—defining clear project milestones, developing action plans, and removing blockers to achieve goals
• Experience facilitating leadership meetings, business reviews, and planning off-sites
• Authorized to work lawfully in the United States of America as Calendly does not engage in immigration sponsorship at this time

Responsibilities

• Driving GTM strategic planning and OKR management—partnering with GTM leaders to define, track, and report on objectives and key results, and preparing leadership updates and monthly business reviews
• Establishing and owning the rhythm of the GTM business, including running leadership and team meetings, quarterly off-sites, and operational checkpoints
• Building and maintaining dashboards and reporting tools to provide data-driven insights on GTM performance and ensure accountability
• Optimizing and streamlining workflows between GTM sub-teams and cross-functional partners to improve efficiency at scale
• Identifying, leading, and executing high-impact special projects—everything from integrated ops plan development and rebrand PM support to voice-of-customer initiatives
• Supporting change management for new tools, processes, and GTM initiatives, acting as the primary point of contact for ad hoc process needs
• Serving as a trusted advisor to GTM leaders, proactively surfacing opportunities for improvement and removing blockers to keep projects on track

Benefits

• Ready to make a serious impact? Millions of people already rely on Calendly’s products, and we’re still in the midst of our growth curve — 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