Director of Customer Success

About the team/role

As a Director of Checkrs Strategic Customer Success team, you will lead a team of 5 experienced Customer Success Managers who are assigned to Checkrs 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 Checkrs 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.