Serve as the single-threaded owner for a major, enterprise customer relationship
Develop and execute a multi-year account strategy that drives employee engagement, ROI, retention, and expansion
Build and sustain trusted relationships across all levels of a large organization, including senior and executive stakeholders
Act as a strategic advisor, challenging customer thinking and influencing decisions through insights, storytelling, and data
Proactively manage and improve customer health, ensuring Brightside meets or exceeds engagement goals and contractual commitments
Lead renewal and expansion efforts, grounded in data and demonstrated value and outcomes
Translate customer feedback into clear, actionable insights that shape Brightside’s product roadmap, services, and go-to-market strategy
Identify and deliver creative, consultative solutions to complex workforce financial health challenges
Serve as a subject matter expert on Brightside’s platform, services, and best practices
Navigate the complexity of large, multi-stakeholder accounts across different stages of maturity and adoption
Help define and evolve Customer Success strategy, playbooks, and standards across the organization
Mentor and influence other Customer Success leaders, setting the bar for strategic account excellence

8+ years of experience owning complex, enterprise customer relationships (financial services, healthcare, benefits, or consulting preferred)
Proven success managing large, high-stakes accounts with executive stakeholders
Track record of leading renewals, driving expansion, and introducing innovation through value-based strategy
Strong executive presence with the ability to influence HR, Finance, Benefits, and C-suite leaders
Comfort operating in ambiguity with the ability to create clarity, structure, and momentum
Highly consultative, data-informed, and outcomes-oriented approach
Strong internal collaborator who builds credibility across Product, Sales, Technology, and Operations
Deep commitment to acting in the best interest of the customer while advancing Brightside’s mission and growth.

For our clients
our mission is clear. To improve the financial health of working families. Brightside is an employee benefit with a brand new approach to personal finance. We offer unique solutions to help with anything related to finances, emotions and behaviors that can impact our clients. We take a holistic view to provide unbiased and confidential assistance through an unmatched blend of products, technology and true human care. Our goal is to make it easier for our clients to understand their options to obtain long-term financial health and gain peace of mind when it comes to financial matters.
For our employees
we believe in inspiring careers, a great life/work balance and meaningful work that truly makes a difference in the lives of working families. Your work will have direct impact on the lives of our clients. You will have the opportunity to see a growing start-up from the inside out and see how passionate our employees are about the work we do and the outcomes we are creating for others.

Principal Customer Success Manager

Key skills