Director, Technical Escalations

Gainsight • New York, SC

5d • Remote

About The Position

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.

Requirements

• 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 Haves

• 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

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
• 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

Benefits

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

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed