Principal, Customer Success Manager

Brightside is an innovative company focused on improving the financial health of working families. The Principal Customer Success Manager will lead major enterprise customer relationships, develop long-term strategies, and drive engagement and retention through consultative solutions and relationship management.

Responsibilities:

• 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

Requirements:

• 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