Senior Director of Technical Services

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 Senior Director of Technical Services to join our Services team  reporting to the SVP, Professional Services & Onboarding. This role is a remote role based in the United States. 

In this role, you’ll play a key role in driving customer retention, growth, and value realization of our SaaS products by leading a high-performing team of Technical Account Managers and Solutions Architects. You will play a critical role in driving revenue growth for our Professional Services and product offerings, as well as mentoring and coaching team members to foster a culture of customer excellence.

What You'll Do: 

Customer Value Realization:

• Collaborate with customers to understand their unique needs and ensure they are realizing the full potential of our solutions.

• Advocate for customer requirements within the organization to enhance product adoption and service offerings.

Customer Retention and Growth:

• Develop and implement strategies to ensure high customer satisfaction and retention rates.

• Identify opportunities for growth within existing accounts and drive actionable plans to realize them.

Gainsight Revenue Growth:

• Enable revenue growth across all Gainsights Product lines through effective project delivery and customer partnership.

• Lead the Professional Services ARR (Annual Recurring Revenue) line of business, ensuring profitable operations and growth.

Leading Integrated Account Teams:

• Participate as a leader in crossfunctional teams enabling seamless service and support to customers, ensuring alignment across an integrated account team.

• Promote collaboration and communication among team members to optimize client engagement efforts.

Mentoring and Coaching:

• Provide guidance, mentorship, and professional development opportunities to team members, fostering a growth mindset and a culture of continuous improvement.

• Lead and participate in regular team talent assessments to foster teammate enablement and growth. 

Customer Facing Skills:

• Engage directly with key customers to build strong relationships, understand their challenges, and demonstrate the value of our Products.

• Serve as a trusted advisor to customers, offering solutions that align with their business objectives.

This is not a complete list of responsibilities, and the scope of the role may evolve with the needs of the team and business.

What We're Looking For: 

• Bachelors Degree in Project Management, Business Administration, or a related field and/or Bachelors Degree or 13-15 years of related experience with 9-10 years management experience

• Proven experience (9+ years) in a leadership role within postsales management, professional services, or customer support, preferably in a technology-driven environment.

• Strong consulting background with the ability to understand customer needs and translate them into effective service solutions.

• Deep understanding of customer success principles and experience developing and executing postsales strategies that drive revenue and improve customer satisfaction.

• Familiarity with AI, automation, and other emerging technologies, with a track record of successfully implementing these technologies to enhance service delivery.

• Excellent leadership and team management skills with a demonstrated ability to inspire and develop a diverse global team.

• Exceptional communication and interpersonal skills, capable of engaging with stakeholders at all levels, including executive leadership.

• Strategic thinker with strong analytical skills and the ability to translate insights into actionable plans.

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 $154,000 – $198,000 USD annually. This role is also eligible for commission based on performance and participation in Gainsight’s equity program. Actual compensation may vary based on factors such as skills, experience, and location. 

• 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.