Why This Job is Featured on The SaaS Jobs
Strategic Customer Success leadership roles are pivotal in SaaS businesses where renewals, expansion, and product adoption are tightly linked to long-term revenue. This Director position sits at the enterprise end of the customer base, overseeing outcomes for large, complex accounts and operating as an escalation and alignment point across Sales, Product, Support, and executive stakeholders. The remit signals a mature SaaS operating model where customer success is measured with clear retention and consumption-oriented metrics.
For a SaaS career, the role builds durable experience in turning customer signals into operational improvements at scale. Leading experienced CSMs while managing executive relationships develops the managerial and commercial judgment needed in subscription businesses, especially where value realization must be proven and renewed repeatedly. The emphasis on systemic problem solving, analytics, and process simplification maps closely to how high-performing SaaS teams run post-sale: instrumenting health, diagnosing friction, and coordinating change across functions.
This role best fits a seasoned customer success leader who prefers structured ownership, coaching, and measurable outcomes over purely relationship-based account coverage. It will suit someone comfortable navigating ambiguity, making decisions with data, and representing the customer perspective in internal prioritization conversations, including when tradeoffs are required.
The section above is editorial commentary from The SaaS Jobs, provided to help SaaS professionals understand the role in a broader industry context.
Job Description
About the team/role
As a Director of Checkr’s Strategic Customer Success team, you will lead a team of 5 experienced Customer Success Managers who are assigned to Checkr’s largest and most complex clients. You will be responsible for delivering exceptional value realization, fostering strong, executive-level customer relationships, and ensuring a delightful customer experience. This role reports to the Senior Director of Customer Success.
You will be accountable for achieving ambitious account goals, enhancing operational efficiency, and providing exceptional leadership and mentorship to your team members. You will collaborate closely with cross-functional professionals who thrive on collaboration, grit, and continuous learning. Your leadership will be vital in maintaining a culture of excellence, acting with integrity and transparency, and serving as a trusted advisor to your team and our customers. You will ensure the overall health and success of Checkr’s most strategic accounts, contributing to logo retention, gross dollar retention, and net revenue per check.
What you'll do
- Lead and develop a high-performing team: Recruit, mentor, and manage a team of experienced Customer Success Managers, fostering their professional growth, encouraging decentralized decision-making, and ensuring they have the tools and support to excel in a complex strategic environment.
- Oversee strategic customer relationships: Ensure strategic alignment with customers, acting as an escalation point for critical issues and fostering strong, trust-based partnerships at SVP, VP, and Director levels within customer organizations.
- Drive customer success strategy: Develop and implement strategies to maximize customer value realization, satisfaction, and retention across your portfolio. You will look beyond specific challenges to identify and address systemic improvement opportunities.
- Collaborate cross-functionally: Partner with Sales, Account Management, Product, Engineering, Support, and Executive teams to advocate for customer needs, share information openly, and drive continuous improvement in our products and services.
- Achieve operational excellence: Monitor team performance metrics, manage resources effectively, and ensure adherence to best practices while encouraging innovation and simplification in all processes.
- Facilitate account expansion: Collaborate closely with Account Management to identify and pursue account growth and expansion opportunities, aligning with customer goals and delivering additional value.
What you bring
- Experience and Leadership: At least 10 years of experience in Customer Success, Account Management, or related roles, with a minimum of 6 years in a leadership or managerial position, preferably within the HR-Tech or consumptive SaaS markets.
- Problem solving: Demonstrated ability to simplify and solve complex problems using critical thinking, creative approaches, and structure. You are proficient in using data and analytics to solve problems, identify systemic issues, and drive performance improvements.
- Communication: Excellent written and verbal communication skills, able to articulate complex concepts clearly, adapt your communication style to different audiences, including executive leaders, and remain approachable.
- Integrity and Inclusion: Known for candor, transparency, and treating everyone with respect. You work well with different backgrounds, identities, values, and cultures.
- Passion and Drive: Inspire others with your drive for excellence, maintain a tenacious and optimistic attitude, and care deeply about winning and your teammates.
- Willingness to travel: Ability to travel domestically up to 25% for customer engagements and team meetings.
- An A-player mindset with a strong bias for action: you raise the bar, move with urgency, stay resilient through ambiguity, and take ownership to deliver meaningful outcomes.
