Director, Technical Escalations

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, Technical Escalations to join our Customer Success team  reporting to the Chief Customer Officer. This role is a remote role based in The United States.

In this role, you’ll play a key role in protecting Gross Revenue Retention and restoring executive confidence by owning and driving the company’s most complex, business-critical technical escalations. You’ll operate as the single-threaded escalation leader—translating technical failures into clear business impact, directing cross-functional teams to resolution, and ensuring durable corrective action. This is a great opportunity for someone who thrives in high-pressure, ambiguous environments and enjoys working cross-functionally with Customer Success, Support, Engineering, Product, Sales, and Professional Services, often with direct executive visibility. The ideal candidate brings deep experience leading SaaS technical escalations, strong technical credibility across platforms like Salesforce or Dynamics, and the executive presence to drive decisions, accountability, and outcomes across organizational boundaries.

What You'll Do: 

• Core Responsibilities

  • Own and lead the company’s most critical technical escalations, particularly those involving executive customers, multi-product complexity, or material revenue risk

  • Act as the single-threaded escalation owner, accountable from intake through stabilization and formal exit

  • Translate technical failures into clear business impact, ensuring resolution paths align to customer outcomes and retention goals

  • Diagnose root cause through close partnership with Support, Engineering, Product, and Solutions leaders

  • Direct cross-functional escalation teams, clearly defining ownership, expectations, timelines, and success criteria

  • Lead executive-level internal and external escalation meetings with structured communication and clear decision points

  • Maintain escalation prioritization, action plans, and executive summaries for leadership visibility

  • Drive post-escalation reviews to surface systemic issues and reduce repeat failures

  • Partner with the RDR Program Lead to evolve escalation criteria, operating cadence, and scale readiness
     

• Red Account Process & Cadence

  • Own and run the company’s red account operating cadence, including:

    • Defining red account criteria and escalation thresholds

    • Maintaining the prioritized red account list

    • Leading a regular red account review / risk call with cross-functional leaders

  • Ensure each red account has:

    • A clear risk statement and business impact

    • A defined recovery plan with owners and timelines

    • Active executive visibility where required

  • Escalate decision blockers quickly and ensure risks do not stall due to ambiguity or ownership gaps

Travel Requirement: This role may require occasional travel (~15%) for team meetings, training, or company events.

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: 

• 10+ years of relevant experience leading complex, high-impact technical escalations in a SaaS environment

• Strong technical foundation in Salesforce (SFDC) or Microsoft Dynamics

• Experience in Support, Solutions Engineering, or technical customer-facing leadership roles

• Solid understanding of modern SaaS architectures and current technology trends

• Ability to operate independently with minimal oversight and high executive exposure

• Working knowledge of SQL, REST APIs, and experience communicating with executive leadership strongly preferred
   

Nice-to-have skills:

• Executive driver mentality: unblocks progress, forces decisions, and holds teams accountable across organizational boundaries

• Strong executive communicator: controls the narrative, drives clarity, and earns trust with C-level stakeholders

• Technically credible: able to engage deeply with engineering and support while simplifying complexity for executives

• Outcome-focused: biased toward durable, scalable solutions rather than short-term workarounds

• Comfortable in ambiguity: thrives in high-pressure, incomplete-information environments

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 $135,000 – $150,000 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.