Sr. Director Client Success, SME

About Us:

DailyPay, Inc. is transforming the way people get paid. As the industry’s leading on-demand pay solution, DailyPay uses an award-winning technology platform to help America’s top employers build stronger relationships with their employees. This voluntary employee benefit enables workers everywhere to feel more motivated to work harder and stay longer on the job, while supporting their financial well-being outside of the workplace. DailyPay is headquartered in New York City, with operations in Minneapolis and Belfast. For more information, visit DailyPay's Press Center.

The Role:

Join our team as the Senior Director of Client Success, SME and take charge of driving measurable human capital management outcomes for DailyPay SME clients.  You will lead a team responsible for growing the eligible, enrolled, and adopted employee base within each SME client by introducing and influencing employer financial wellness best practices and communication channels while managing high-level client escalations, and fostering strong client stakeholder relationships. As a key member of our leadership team, you will advocate for both your team and our clients, contributing to product and marketing roadmap improvements and ensuring Annual Operating Plan targets are met.  

Reporting to the Chief Customer Officer, the Sr. Director of Client Success, SME will be responsible for the development, improvement and execution of strategies (success plays) that maximize end-user enrollment and adoption while ensuring client retention with an industry-leading experience for our Small Medium Enterprise (SME) customers (with less than 2,000 employees).

If this opportunity excites you, we encourage you to apply even if you do not meet all of the qualifications.

How You Will Make an Impact:

• Organization / Personnel
      •    Build, motivate, and lead a high-performance in-office and remote Client Success Team.
      •    Support career development through measurable OKRs and performance feedback.
      •    Provide recognition for individual, team, and cross-functional achievements.
• Go-To-Market
      •    Facilitate executive decision-making to support a ~600 client book of business.
      •    Partner with sales and leadership to close pipeline deals and set expectations.
      •    Collaborate with Marketing to grow the end-user population throughout the customer lifecycle.
      •    Work with CS Enablement to drive revenue through cross-sell and up-sell opportunities.
      •    Support the creation of Success Plays and other assets for GTM initiatives.
      •    Minimize client operational losses in collaboration with Payments, Trust and Safety, and other teams.
      •    Manage customer escalations and ensure prompt resolutions.
      •    Deliver impactful QBRs with senior customer management.
      •    Stay ahead of market risks and competitive differentiators, providing actionable churn risk insights.
• Governance / KPIs
      •    Manage individual and team CS KPIs (Net Enrolled Retention, Churn, and CSM scorecard).
      •    Focus on quarterly and annual KPI goals related to Enrollment, Adoption, Permissions, and NPS/CSAT.
      •    Lead pipeline management for upsell and cross-sell opportunities using Catalyst.
      •    Maintain Catalyst account health fields to predict churn indicators.

What You Bring to The Team:

• BA/BS degree in Business Administration, Sales, or a relevant field (or equivalent experience)
• Leadership Experience: Proven experience leading GTM teams through the client lifecycle , preferably in a SaaS environment
• Strategic Mindset: Ability to drive product roadmap improvements and develop retention strategies for at risk clients
• Performance Management: Experience in managing KPIs to drive team success and achieve strategic outcomes
• Problem-Solving Skills: Exceptional problem-solving abilities and the capacity to thrive in a fast-paced, dynamic environment
• Collaboration and Innovation: Commitment to fostering a culture of collaboration, innovation, and continuous improvement
• Enterprise Customer Success Expertise: Deep understanding of Enterprise CS models driving Business Results and CLV, with a minimum of 5+ years in Customer Success
• Team Management: Experience managing a team of CSMs and developing, scaling, and managing a high-performing CS team
• Industry Knowledge: 10+ years in SaaS, specifically in Payroll/TMS/HCM/Benefits/Technology, with some time in business development or sales
• Effective Communication: Strong communication and collaboration skills, with the ability to represent the team in high-st