Director of Customer Success

The Director of Customer Success leads a team of 10 CSMs across two segments — Enterprise and Mid-Market — and owns retention and expansion outcomes across that entire portfolio. This is a proactive account management function, distinct from support, training, and sales.

Leadership and Team Management

• Lead, coach, and develop a team of 10 CSMs across Enterprise and Mid-Market segments, recognizing the distinct skills, engagement approaches, and demands each segment requires.
• Set clear expectations and build individual development plans tailored to each CSM's role, experience level, and portfolio complexity.
• Conduct consistent 1:1s and team meetings that drive accountability, skill development, and alignment to CS strategy across all segments.
• Own the hiring and onboarding of new CSMs, ensuring they ramp effectively and integrate into team culture.
• Build and scale a high-performance, customer-centric team culture grounded in ownership and continuous improvement.
• Build and maintain systems that enable, motivate, and drive accountability around team targets.
• Coach team members through day-to-day challenges while guiding mid- to long-term career path development within Customer Success.
• Serve as the senior escalation point for complex or at-risk accounts across the full portfolio.

Customer Success Strategy & Execution

• Own the engagement model strategy across all tiers, ensuring CSMs deliver strategic, high-touch partnerships as well as efficient, scalable outcomes appropriate to each segment.
• Monitor portfolio health using ChurnZero and Salesforce across the team, identifying at-risk accounts early and guiding CSMs through appropriate intervention strategies.
• Lead the development and execution of the expansion strategy across all tiers, ensuring alignment and coverage across the portfolio.
• Ensure CSMs are conducting high-quality executive business reviews and maintaining strong executive sponsor relationships.
• Hold CSMs accountable to implementing meaningful success plans for their accounts, with clear goals, milestones, and ownership, and hold them accountable to driving progress against those plans.

Retention and Growth

• Own team-level GRR and NRR performance across Enterprise and Mid-Market accounts, tracking trends and insights.
• Ensure early and consistent risk identification across all portfolios — coaching CSMs to recognize warning signs, escalate appropriately, and execute structured mitigation plans before accounts reach a critical stage.
• Drive a proactive expansion culture on the team, ensuring CSMs understand their customers' growth potential and are positioning expansion conversations as a natural extension of customer success, not a separate sales motion.
• Proactively identify patterns in churn risk and customer dissatisfaction, delivering data-backed recommendations to drive retention strategy at the organizational level.
• Represent Customer Success in cross-functional retention initiatives, coordinating across Sales, Product, and Support to manage termination risk on the highest-priority accounts.

Cross-Functional Collaboration

• Coordinate with the Implementation team to support smooth customer handoffs and establish a strong retention foundation for all customers.
• Partner with the Support team to facilitate timely escalation resolution and maintain consistent case management practices across all segments.
• Work closely with the Solutions Advisory team to align on customer strategy and solution fit throughout the customer lifecycle.
• Represent Customer Success with Product leadership, surfacing voice-of-customer feedback and portfolio insights to inform roadmap decisions and tooling improvements.
• Partner with Sales leadership on renewal and expansion motions, ensuring a seamless customer experience across the pre- and post-sale lifecycle.
• Maintain a strong feedback loop with Product and other stakeholders to channel customer insights and learnings back into the business.
• Partner with People/Talent on the CSM career ladder, leveling, and compensation structure as the team grows.

Reporting and Insights

• Create and maintain KPIs that reflect the health and performance of the team.
• Maintain accurate, up-to-date portfolio health data in ChurnZero and Salesforce across the team.
• Partner with the VP of Customer Success to track and report on key metrics including retention rates, health scores, product adoption, and engagement quality across all segments.
• Contribute CS performance data and insights to broader business reviews and retention-focused leadership discussions.

Qualifications

• 6-8 years in B2B SaaS customer success, with 3-5 years in leadership.
• Experience working across multiple customer segments, including enterprise accounts with complex stakeholder environments and mid-market accounts, with a proven ability to manage competing priorities, align diverse stakeholders, and deliver consistent, high-quality customer experience across all tiers.
• Demonstrated ability to drive GRR and NRR outcomes across a mixed portfolio, with experience reporting results to senior leadership.
• Strong experience executing CS playbooks, executive business reviews, and renewal/expansion motions across varying account tiers.
• Proven coaching ability with the range to develop CSMs operating in different engagement models and at different career stages.
• Data-driven mindset with hands-on experience using CS platforms (ChurnZero, Gainsight, or equivalent) and Salesforce.
• Demonstrated operational excellence in problem-solving, analytical thinking, process development, and planning.
• Comfortable operating cross-functionally alongside Sales, Implementation, Product, and Support teams, including at the leadership level.
• Experience contributing to cross-functional retention initiatives spanning multiple product lines or business units a plus.
• Financial services or GRC experience a plus.
• Bachelor's degree preferred.