Brightside

• Own the product strategy and roadmap for Brightside’s client app • Design and optimize client journeys that drive activation and engagement • Build experiences that bridge digital and human support • Define and implement engagement loops • Partner with design, engineering, data, and operations teams • Use data and user insights to improve engagement and outcomes

• Lead, hire, and develop a high-performing Client Intelligence engineering team • Drive clarity, accountability, and predictable delivery across multiple initiatives • Foster a culture of ownership, engineering excellence, and continuous improvement • Coach engineers through hands-on guidance, feedback, and career development • Design and build AI agents and workflows that automate complex processes and improve productivity • Identify bottlenecks and deploy AI-driven solutions to reduce manual work • Establish best practices for agent orchestration, tool integration, prompt design, evaluation, and observability • Promote adoption of modern AI engineering practices across the organization • Own technical direction for client intelligence systems, AI workflows, and supporting data architecture • Contribute to code in Python, TypeScript, and backend systems • Partner with data teams on data lake strategy, modeling, governance, and reliability

• Own day-to-day accounting activities, including accurate transaction recording and system integrity in Campfire • Manage accounts payable processes in Bill.com, ensuring proper approvals, coding accuracy, and timely processing • Process bi-weekly multi-state payroll in Rippling, ensuring compliance with all applicable regulations • Maintain accuracy and completeness of general ledger activity • Execute and help drive the monthly close process to ensure timely and accurate reporting • Prepare and review balance sheet reconciliations, identifying and resolving discrepancies proactively • Ensure completeness, accuracy, and consistency of financial data across systems • Identify close bottlenecks and recommend improvements • Investigate and explain variances in financial results with clear, supportable analysis • Prepare supporting schedules and documentation for internal reporting • Maintain well-organized, audit-ready workpapers • Support internal and external audits, including preparation of documentation and responding to requests • Ensure adherence to accounting policies and regulatory requirements • Assist with compliance-related processes such as workers’ compensation audits • Document and maintain accounting policies and procedures • Identify opportunities to improve efficiency, accuracy, and internal controls • Drive implementation of process improvements within the accounting function • Partner with stakeholders across the business to ensure smooth financial operations • Communicate clearly and effectively with finance leadership and business partners • Respond to inquiries with timely, accurate, and well-supported information

• 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

• Lead the overall development and execution of Brightside’s multi-channel client engagement strategy, ensuring alignment with customer success goals and business priorities • Develop the 2026 Client Engagement and Communications Plan in partnership with Customer Success and other internal stakeholders • Ensure all client engagement activities reinforce Brightside’s brand voice, values, and engagement objectives • Act as the primary strategic liaison between Marketing, Customer Success, and Product, ensuring cohesive communication strategies across all touch points • Oversee the planning and deployment of targeted, segmented engagement campaigns across email, mailers, push notifications, and in-app messaging • Set and manage deployment schedules for major campaigns (e.g., Consolidated Credit, Student Loan Wage Garnishments, Free Financial Tools) • Direct the creation of campaign briefs, timelines, and execution plans to ensure timely delivery and cross-team coordination • Ensure campaign deliverables are error-free, on-brand, and optimized for engagement and conversion • Provide creative direction and feedback on all marketing and communication materials, ensuring consistent messaging and design across channels • Oversee the evolution of Brightside’s visual and narrative identity to support client engagement goals and campaign differentiation • Collaborate with internal design, content, and product teams to translate business objectives into compelling, actionable creative outputs • Review, analyze, and synthesize campaign performance data to identify insights and optimize engagement strategies • Establish frameworks for reporting and continuous learning across clients and channels • Maintain and evolve marketing project documentation and playbooks to ensure ongoing alignment with Brightside’s strategic objectives • Participate actively in cross-functional meetings, sharing updates, priorities, and insights to inform decision-making and alignment

• Own the data and AI architecture across the company, spanning: AI-powered systems and decisioning workflows, Core application platforms, Analytics and reporting layers • Define and evolve canonical data models across clients, employers, partners, financial products, and outcomes • Ensure consistency across transactional systems, analytical platforms, and AI feature layers • Act as the company’s data strategy expert, with deep understanding of: Employer integrations (eligibility, payroll, SSO, identity), Partner integrations and product data, External and enrichment data sources (e.g., credit, public datasets) • Identify which data sources meaningfully compound business and product value, and which do not • Guide integration and platform investments based on data leverage and long-term value, not just feature demand • Design and govern production-grade AI systems, including: LLM-based applications (RAG, prompt orchestration, embeddings, vector stores), Decisioning and automation workflows • Evaluate and govern AI models and platforms (e.g., OpenAI, Anthropic, open-source), balancing: Accuracy and reliability, Cost and latency, Security, privacy, and explainability • Define standards for AI lifecycle management (build, deploy, monitor, iterate, retire) • Act as the decision-maker for data and AI architecture decisions across engineering teams • Partner with the Enterprise Architecture Board to review proposals, surface risks, and ensure coherence • Establish clear architecture standards and review processes that enable teams to move fast without creating long-term risk or technical debt • Lead rapid prototyping and technical discovery to: Test architectural assumptions, Evaluate new AI approaches, Inform investment and roadmap decisions • Personally build or lead proofs-of-concept where needed to drive alignment and reduce uncertainty • Partner closely with the CTO, Product leaders, Analytics, and Engineering to: Translate business strategy into technical direction, Align data, AI, and platform investments, Serve as a trusted technical advisor to executive leadership on data, AI, and platform tradeoffs

A bit about this role: The Principal, Lifecycle Client Marketing will lead the development, execution, and optimization of all marketing and engagement strategies across assigned customer portfolios. This role oversees creative direction, partner communications, and cross-channel engagement strategies that drive measurable impact through email, direct mail, in-app messaging, employer training events, and other engagement strategies. The meaningful work you will tackle: - Client Engagement Strategy & Leadership - - Lead the overall development and execution of Brightside’s multi-channel client engagement strategy, ensuring alignment with customer success goals and business priorities - Develop the 2026 Client Engagement and Communications Plan in partnership with Customer Success and other internal stakeholders - Ensure all client engagement activities reinforce Brightside’s brand voice, values, and engagement objectives - Act as the primary strategic liaison between Marketing, Customer Success, and Product, ensuring cohesive communication strategies across all touch points - Campaign Planning & Execution - - Oversee the planning and deployment of targeted, segmented engagement campaigns across email, mailers, push notifications, and in-app messaging - Set and manage deployment schedules for major campaigns (e.g., Consolidated Credit, Student Loan Wage Garnishments, Free Financial Tools) - Direct the creation of campaign briefs, timelines, and execution plans to ensure timely delivery and cross-team coordination - Ensure campaign deliverables are error-free, on-brand, and optimized for engagement and conversion - Creative Direction & Brand Stewardship - - Provide creative direction and feedback on all marketing and communication materials, ensuring consistent messaging and design across channels - Oversee the evolution of Brightside’s visual and narrative identity to support client engagement goals and campaign differentiation - Collaborate with internal design, content, and product teams to translate business objectives into compelling, actionable creative outputs - Performance Analysis & Continuous Improvement - - Review, analyze, and synthesize campaign performance data to identify insights and optimize engagement strategies - Establish frameworks for reporting and continuous learning across clients and channels - Maintain and evolve marketing project documentation and playbooks to ensure ongoing alignment with Brightside’s strategic objectives - Participate actively in cross-functional meetings, sharing updates, priorities, and insights to inform decision-making and alignment What we’re looking for in your background & what makes you a success: - 5+ years of experience in a Marketing role - client marketing required - The use of modern marketing tools, like Salesforce Marketing Cloud/Hubspot, Jira, Asana and use of AI - Demonstrable knowledge of best practices in B2B right demand generation, account-based marketing, content marketing, marketing automation, and lead nurturing - Experience in project management and building integrated online campaigns - Strong analytical and quantitative capability to determine program effectiveness, ROI, etc - Ability to collaborate and work cross-functionally with our internal stakeholders - Strong experience with Google and other communication tools (Gmail, Docs, Sheets, Slides, Slack, etc) - Exceptional presentation, communication, and organizational skills - Strong knowledge of marketing & sales automation tools and platforms

A bit about this role: Brightside is seeking a Principal Architect, Data & AI Platforms, to own and evolve the technical foundations that power our AI-driven experiences, platform integrations, and analytics. This is a senior, hands-on architecture role designed for someone who combines deep data architecture expertise, strong applied AI judgment, and the ability to translate business strategy into durable technical systems. This role reports directly to the CTO and serves as the CTO’s right-hand partner for data, AI, and platform architecture decisions. You will have clear decision authority over data and AI architecture across engineering teams, while partnering closely with Product, Analytics, and Engineering leadership to ensure speed, quality, and long-term integrity. This is not a research role, nor a people-management role. It is an execution-oriented architecture leadership role focused on clarity, leverage, and outcomes. The meaningful work you will tackle: Enterprise Data & AI Architecture - Own the data and AI architecture across the company, spanning: - AI-powered systems and decisioning workflows - Core application platforms - Analytics and reporting layers - Define and evolve canonical data models across clients, employers, partners, financial products, and outcomes - Ensure consistency across transactional systems, analytical platforms, and AI feature layers Data Strategy & Integration Leverage - Act as the company’s data strategy expert, with deep understanding of: - Employer integrations (eligibility, payroll, SSO, identity) - Partner integrations and product data - External and enrichment data sources (e.g., credit, public datasets) - Identify which data sources meaningfully compound business and product value, and which do not - Guide integration and platform investments based on data leverage and long-term value, not just feature demand AI System Design & Governance - Design and govern production-grade AI systems, including: - LLM-based applications (RAG, prompt orchestration, embeddings, vector stores) - Decisioning and automation workflows - Evaluate and govern AI models and platforms (e.g., OpenAI, Anthropic, open-source), balancing: - Accuracy and reliability - Cost and latency - Security, privacy, and explainability - Define standards for AI lifecycle management (build, deploy, monitor, iterate, retire) Architecture Authority & Decision-Making - Act as the decision-maker for data and AI architecture decisions across engineering teams - Partner with the Enterprise Architecture Board to review proposals, surface risks, and ensure coherence - Establish clear architecture standards and review processes that enable teams to move fast without creating long-term risk or technical debt Prototyping & Technical Discovery - Lead rapid prototyping and technical discovery to: - Test architectural assumptions - Evaluate new AI approaches - Inform investment and roadmap decisions - Personally build or lead proofs-of-concept where needed to drive alignment and reduce uncertainty Executive & Cross-Functional Partnership - Partner closely with the CTO, Product leaders, Analytics, and Engineering to: - Translate business strategy into technical direction - Align data, AI, and platform investments - Serve as a trusted technical advisor to executive leadership on data, AI, and platform tradeoffs How You’ll Work - Hands-on, opinionated, and pragmatic - Focused on clarity over complexity - Comfortable saying “no” to poor architectural decisions - and explaining why - Oriented toward production outcomes, not theoretical elegance - Balancing experimentation with rigor in a regulated fintech environment What we’re looking for in your background & what makes you a success: - 10+ years of experience in software engineering, data architecture, or systems architecture, with significant hands-on experience - Deep expertise in data architecture and data modeling, including relational databases, event-driven systems, and analytical data platforms - Strong experience designing and operating data platforms at scale, including data lakes/warehouses and real-time pipelines - Strong experience designing and operating AI/ML systems in production, including LLM-based architectures (RAG, embeddings, vector databases, prompt orchestration) - Proven experience in regulated environments (fintech, financial services, healthcare, etc.), with an understanding of data privacy, security, and compliance requirements - Strong in modern cloud architectures (e.g., AWS) and modern data stacks (e.g., Databricks) - Ability to connect technical decisions to business outcomes, including cost efficiency, scalability, risk mitigation, and customer experience - Strong communication skills and comfort influencing across engineering, product, and executive leadership - Experience serving as a Lead Architect in a high-growth or transformation-stage company - Background in financial systems, payments, lending, or financial data platforms - Experience with AI governance, model risk management, or explainability frameworks - Track record of improving engineer productivity through platform and architecture design

A bit about this role: 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 What we’re looking for in your background & what makes you a success: - 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 - 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

This description is a summary of our understanding of the job description. Click on 'Apply' button to find out more. 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