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