Principal Strategic Engagement Manager

Role Overview

• Architect, orchestrate, and ensure delivery of large-scale, cross-functional initiatives that drive measurable business outcomes and maximize client success and Gainsight value
• Guide the design of scalable program governance, delivery, and measurement approaches, ensuring optimal resource deployment, margin optimization, and client satisfaction
• Represent Gainsight as an executive sponsor in critical customer forums, executive business reviews, and SteerCo sessions, influencing decisions and building customer advocacy
• Represent Gainsight as the executive point of escalation, negotiating complex issues and ensuring client relationships remain strong and mutually beneficial
• Partner with executive sponsors (both client and Gainsight) to define both short and long-term program roadmaps and drive alignment between client business outcomes and Gainsight’s offerings
• Build and nurture trusted, executive–level relationships within client organizations, advocating for strategic partnership and executive alignment
• Support the definition of long-term account strategy by anticipating evolving client business objectives and proactively identifying opportunities for value delivery, innovation, and expansion
• Partner with internal stakeholders to identify and secure strategic cross-functional resources, influence product direction, and drive company-wide alignment for key accounts
• Serve as a visible leader and mentor within the Professional Services organization—coaching, developing, and elevating program management excellence and thought leadership.

Requirements

• 10+ years of relevant experience in enterprise program or project management, professional services, management consulting, or customer success, with a track record of managing global, strategic accounts
• Bachelor’s degree required; advanced degree (e.g., MBA, MS in Engineering) or equivalent experience preferred
• Demonstrated success leading large service contract programs with Fortune 500 clients, including experience with multi-year, multi-business-unit engagements
• Executive-level stakeholder management and advisory experience (C-suite engagement required)
• Proven ability to design and scale program and project management frameworks or methodologies across a professional services organization
• Experience leading and mentoring others, fostering talent development at scale
• Outstanding executive communication, strategic thinking, negotiation, and influencing skills
• Expert proficiency in program/portfolio management tools, CRM software, and data analytics platforms
• Willingness to travel as needed (up to 20%), including global travel
• PMP, PgMP, or similar advanced project/program management certification

Tech Stack

• PMP

Benefits

• fully covered medical premiums (employee-only)
• flexible PTO
• 401(k) plan
• dental and vision coverage
• remote work options
• $10,000 lifetime fertility stipend
• access to coworking spaces around the globe
• dedicated Recharge Holidays
• one long weekend each quarter to relax and reset