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Role Description

The Principal Customer Success Manager is the most senior individual-contributor role within Brightside’s Customer Success organization. This role owns one of Brightside’s largest and most complex employer partnerships and is accountable for driving long-term strategy, engagement, retention, and growth.

This leader operates as a strategic partner and advocate, representing Brightside’s value, innovation, and point of view externally, while translating customer needs, insights, and opportunities into internal action across Product, Marketing, Technology, Sales, and Operations. Success in this role requires a consultative mindset, creativity, executive presence, and the ability to navigate ambiguity while delivering measurable outcomes.

This is not a traditional CSM role. It is a strategic account leadership position designed for someone who thrives at the intersection of relationship management, data-driven engagement strategy, and creative problem-solving. This role has an outsized impact on Brightside’s growth, on our most strategic customer partnerships, and on the financial well-being of thousands of employees. The Principal Customer Success Manager sets the standard for how Brightside shows up as a trusted, indispensable partner.

The meaningful work you will tackle:

• 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

Qualifications

• 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

Requirements

• Sustained employee engagement and adoption
• Clear articulation of business impact and ROI
• Strong executive sponsorship and trust
• High retention and meaningful account growth
• Internal teams aligned around customer priorities and insights