Director, Professional Services Operations

We’re building the AI-driven future of customer success, from retention to growth! Gainsight is the AI-powered retention engine behind the world’s most customer-centric companies. The Gainsight CustomerOS platform orchestrates the customer journey from onboarding to outcomes to advocacy. More than 2,000 companies trust Gainsight’s applications and AI agents to drive learning, adoption, community connection, and success for their customers. To explore how our suite of solutions is shaping the future of customer success, check out the link.  About This Role: We’re looking for a full-time Director, Professional Services Operations to join our Services team reporting to the Senior Director, Services Products. This role is a remote role based in the United States.  In this role, you’ll play a key role in scaling and optimizing Gainsight’s Professional Services operations by driving operational excellence across PS Operations and Deal Desk for a multi-product services business. This is a great opportunity for someone who thrives in a fast-paced, execution-focused environment and enjoys working cross-functionally with Sales, Professional Services, Finance, Partner, and Product teams. The ideal candidate brings strong skills in operational leadership, process optimization, and managing global teams. What You'll Do:  Manage the repository of PS operational content, including offering calculators, SOW templates, SKUs, and packaging. Execute the PS offer release process, ensuring coordination across Sales, Finance, Legal, and Delivery. Enforce opportunity data standards and manage approval workflows to ensure efficient SOW redlines and deal triage. Maintain naming, SKU, and pricing consistency to support repeatability and partner scale. Administer the internal PS tech stack and ensure governance and output standards are met. Implement prioritized AI and automation initiatives to increase accuracy and reduce manual effort. Collaborate with Product and internal tooling teams to operationalize AI use cases within PS workflows. Maintain the PSA platform, ensuring data accuracy, reporting reliability, and system stability. Support operations for SFDC, Services CPQ, Trello scoping workflows, and Workrails contract automation. Monitor data quality, forecasting, utilization, and delivery insights to drive continuous improvement. Ensure systems consistently support the operational needs of ARR services and partner delivery. Manage PS Sales Operations processes, including pricing governance, quoting workflows, and partner services coordination. Update and distribute enablement materials such as offer guides, battle cards, and objection handling frameworks for sellers and partners. Oversee automated partner workflows to ensure partner-delivered engagements adhere to standardized processes. Partner with Sales leadership to resolve operational friction and improve the seller experiences Manage and mentor a team of four analysts across the US and India. Guide the Deal Desk team to focus on strategic operational impact and efficient sales support. Foster analyst autonomy in reporting, data management, and daily problem-solving. Uphold clear standards, operating rhythms, and documentation to ensure team consistency. This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business. This role will require occasional travel for team meetings, training, or company events. What We're Looking For:  7+ years in PS Operations, Deal Desk, or RevOps with experience managing operational workflows in a PS business. Experience with PSA platforms. Experience executing AI and automation initiatives in operational workflows. Proven ability to lead distributed teams and collaborate effectively with cross-functional partners. Strong operational discipline and comfort working in a multi-product environment. Experience maintaining enablement materials such as offer guides, playbooks, and positioning briefs for Sales and partners. Why You’ll Love It Here: Gainsight is a place where innovation is shaped through collaboration, curiosity, and a shared focus on solving real-world problems. With a growing suite of products across customer success, product experience, community, education, and AI-powered relationship intelligence, we continue to evolve with the needs of our customers. When people with diverse strengths, a strong sense of community, and true passion for our mission come together, they drive greater impact and create lasting value. What underpins it all is a culture that offers the stability, trust, and support that people need - not just to do the job, but to show up as themselves and feel connected to the work they do. Gainsters love working here for several reasons. Here are a few: Our Compensation and Benefits: At Gainsight, we believe great work happens when teammates feel fully supported.  The starting base salary range for this role is $170,000 – $185,000 USD annually. Actual compensation may vary based on factors such as skills, experience, and location. In addition to base pay, this role is eligible for an annual bonus and participation in Gainsight’s equity program.  We offer a comprehensive benefits package including fully covered medical premiums (employee-only), flexible PTO, 401(k) plan, dental and vision coverage, and remote work options. Additional benefits include a $10,000 lifetime fertility stipend and access to coworking spaces around the globe. You'll also enjoy dedicated Recharge Holidays - one long weekend each quarter to relax and reset. Our Core Values: We are guided by our values and our mission to be living proof you can win in business while being Human-First. Learn more here. Our Growth Opportunities: From mentoring to career development opportunities, we’re passionate about helping our teammates learn, grow, and thrive. Our Parody Videos: No explanation needed. Just watch them here! If this sounds like the right role for you, we’d love to hear from you. Additional Information: We’re committed to creating an inclusive, fair, and transparent hiring process. As an equal opportunity employer, we celebrate diversity and are committed to creating a welcoming experience for all candidates. If you require accommodations or have questions about how your personal data will be used during the hiring process, please let the recruiting team know.  If you are based in San Francisco, we will consider qualified applicants with arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance.