Director, Customer Success (Enterprise)
RemoteUnited States or Canada
Job Summary
Lead a team of Enterprise CSMs to own the segment's NRR outcomes, engagement model, and team performance. Drive retention, expansion pipeline generation, and executive business review quality while maintaining forecasting accuracy across the full post-sale success motion. Partner with Sales, RevOps, Solutions Engineering, and Product to define collaboration models, manage complex renewals, and aggregate customer intelligence for GTM strategy. Design and scale Enterprise CS engagement models, success planning standards, and AI-assisted workflows that improve team-wide performance and create repeatable outcomes. Serve as the senior escalation owner for critical customer situations and align stakeholders on segment strategy.
Required Qualifications
- 10+ years in Customer Success, enterprise account management, or a strategic post-sale function in SaaS
- demonstrated track record of owning NRR and expansion outcomes
- 10+ years of people management experience
- demonstrated progression in leading and developing CSMs at multiple levels
- Proven ability to lead Enterprise-focused CS teams through complex renewals, executive stakeholder engagement, and commercial expansion motions
- Deep familiarity with CS operating frameworks – success planning, EBR design, risk CTA management, renewal and expansion forecasting
- Strong familiarity with Gainsight and Salesforce
- Experience using CS platforms to manage team performance, customer health, and pipeline visibility at scale
- Demonstrated ability to build, develop, and scale high-performing Enterprise CSM teams across levels
- Sets and reinforces clear performance standards aligned to the CS KPIs
- Structures coaching and development deliberately: formal deal reviews, call debriefs, and development plans that produce measurable improvement in CSM commercial performance
- Owns the Enterprise segment's NRR targets and the discrete Renewals and Pipeline Generation motions
- Partners with Enterprise AEs to define and evolve the CS-Sales collaboration model
- Understands and coaches on multi-stakeholder executive business reviews, C-suite renewal negotiations, multi-year expansion business cases, and competitive retention conversations
- Drives forecasting rigor at the team level
- Uses Gainsight and Salesforce to manage segment health, track CTA resolution, monitor expansion pipeline, and report on team-wide RFS KPI performance
- Designs, documents, and scales Enterprise CS engagement models, success planning standards, EBR methodologies, and playbooks
- Aligns CS capacity, segment coverage models, and role deployment to ARR growth targets and Enterprise customer complexity
- Identifies operating gaps and cross-functional friction; drives structured improvements that reduce risk, accelerate activation, and increase expansion velocity
- Contributes to CS OKR development
- Promotes and models an AI-first approach to commercial execution
- Builds AI-assisted systems for account intelligence, risk monitoring, and engagement preparation
- Serves as senior escalation owner for the Enterprise segment's most critical, high-stakes customer situations
- Trusted partner to Enterprise Sales, Solutions Engineering, RevOps, Support, and Product leadership
- Aligns stakeholders at all levels, including executive audiences, on customer priorities and segment strategy
- Aggregates customer intelligence from the Enterprise book and channels it into GTM positioning, product roadmap input, and CS commercial model design
- Represents the Enterprise CS organization with confidence in leadership forums and strategic planning conversations
- Excellent written and verbal communication skills
- Strong executive presence across internal and customer-facing audiences
- Confident leading with influence rather than authority
- Navigates organizational ambiguity, drives clarity, and aligns cross-functional partners through expertise and relationship
- Champions a culture of enablement, documentation, and shared learning
- Ensures that high-impact workflows, playbooks, and best practices created within the team are made available and usable across the broader CS organization
- This is a remote opportunity within Canada and the US
- USA-based roles only
- Canada-based roles only
Desired Qualifications
- experience managing managers is a strong plus
- Background in cybersecurity, identity security, IAM
- former 1Password power user or practitioner is a meaningful advantage
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