• **About the Role**We are seeking a highly analytical and hands-on Senior Tech AI/ML Product Manager with deep expertise in Machine Learning and Artificial Intelligence and Product Management. • You will define and build a best-in-class job discovery and matching engine that connects users with the most relevant roles for them, at scale. • You will own the strategy, discovery, and delivery of AI-powered features, focusing on matching, ranking, and personalization systems. • The ideal candidate is an entrepreneurial thinker with an engineering mindset, capable of building rapid prototypes, making decisive calls with imperfect data, and relentlessly driving measurable outcomes. **Key Responsibilities** • **Strategy & Ownership:** Define the vision, strategy, and roadmap for AI/ML product features (JobHunt Engine). Take full ownership of the product lifecycle from hypothesis to scaled impact, focusing on business results, not just model performance. • **ML Product Leadership:** Translate business problems into ML hypotheses and solutions. Work side-by-side with ML engineers and data scientists to define data requirements, evaluation frameworks (evals, RAG, agents), model monitoring, and delivery processes. • **Hypothesis Validation & Experimentation:** Design and execute rapid, pragmatic validation cycles. Formulate clear hypotheses (Problem → Mechanism → Impact → Metric), choose the right validation method (A/B test, shadow model, phased rollout), and make data-driven go/no-go decisions under uncertainty. Be scrappy and effective with limited data or infrastructure. • **Structured Problem Solving:** Apply critical thinking to decompose complex, ambiguous problems. Cut through noise, prioritize what truly matters, and build simple, effective solutions first. • **Cross-Functional Execution:** Collaborate closely with Engineering, Data Science, and business teams. Communicate complex ML concepts clearly and align stakeholders on goals, trade-offs, and progress. Expected Outcomes**First 3 Months** • Establish baseline measurement of job supply coverage across the U.S. market, including companies listed in the NASDAQ-100 • Increase the percentage of users who successfully find a job through the platform by **50%**, driven by improvements in matching logic and job relevance **First 6 Months** • Expand job vacancy coverage in the U.S. market, achieving up to **80% coverage of NASDAQ-100 companies** and increasing overall coverage by **30%** • Ship a major upgrade to the resume enhancement feature • Increase the percentage of users who successfully found a job through our platform by 3× **12 Months** • Further expand U.S. job vacancy coverage, achieving a **50% increase** in coverage of NASDAQ-100 companies compared to the 6-month baseline • Double the matching success rate, measured as the percentage of matched vacancies approved as relevant by users • Improve the **application-to-offer conversion rate by 50%**, directly impacting the core business outcome — successful employment

• You will directly work with Tom who is a product person by heart and who has worked on physical and digital products all his life. • Improve LTV per download. (e.g. through paywall testing) • Improve trial start rate. • Coordinate a PR & Marketing campaign together with our Marketing team. • Developing a BI system for analysing user behavior to support retention. • Use Claude Code and other AI tools to automate tasks and workflows. • User interviews to support the ideation for the future of our product.

Role Description We are seeking an experienced and strategic Senior Product Manager to join our growing team. In this role, you'll lead product strategy and delivery across Lively's B2B and B2C product surfaces — from the employer dashboard and broker portal to the employee-facing app and AI powered agent experiences. You'll work at the intersection of healthcare benefits, financial technology, and applied AI, shaping products that directly improve the financial wellbeing of working Americans. This is a high-impact, high-autonomy role. You'll own large initiatives end-to-end, drive cross functional alignment, and operate as the primary subject matter expert for your product areas. If you thrive in fast-paced environments, love ambiguity, and have strong opinions about what it means to build truly great product, we want to meet you. Qualifications - 5+ years of product management experience, with a proven track record of launching and managing software products - Domain experience in healthcare benefits, health insurance, fintech, or financial services — you understand HSA/FSA/HRA plans or can ramp quickly - Bachelor's degree in Business, Marketing, Computer Science, or a related field (MBA is a plus) - Strong familiarity with Agile development methodologies and the full product lifecycle - Excellent analytical and problem-solving skills, with the ability to synthesize complex data into clear product decisions - Deep understanding of choice architecture and how product design influences user behavior - Outstanding communication and interpersonal skills — you can align a room of engineers, designers, and executives on a shared direction - Experience with product management tools such as Jira, Aha!, or similar - Familiarity with analytics platforms (Google Analytics, Mixpanel, Amplitude, or similar) and user testing methodologies - Leadership experience, including mentoring or developing junior PMs Requirements - Experience building AI-powered product experiences — you've shipped LLM-based features, intelligent agents, or AI-assisted workflows and understand how to design for AI reliability, safety, and user trust - Comfort operating in a fast-paced, AI-augmented product environment where tools, processes, and possibilities are evolving quickly - Growth mindset and high self-motivation — you don't wait to be told what the next problem is - Genuine innovation instinct — you bring new ideas to the table, not just execution on someone else's roadmap - Experience spanning both B2B (employer/broker-facing) and B2C (employee/consumer facing) products - Understanding of benefits compliance, IRS regulations, or financial data handling is a meaningful plus Benefits - Competitive salaries - Stock options - Medical, dental, vision, life and disability coverage - An HSA with employer contribution - FSA - Paid parental leave - Medical travel benefits - A 401k plan - Flexible vacation policy - Lifestyle spending accounts - Remote-friendly flexibility

• Own the delivery of core banking integrations and foundational digital banking features end-to-end. • Assist with API definitions, data mapping documentation, and integration requirements across multiple concurrent projects. • Work directly with engineering teams to clarify requirements, validate implementation details, and make technical tradeoffs. • Support testing and validation of integrations prior to client launch. • Monitor post-launch issues and trends to proactively identify root causes and drive product improvements. • Continuously build domain expertise in core banking systems, ACH, payments, and digital banking workflows. • Serve as a primary client-facing product contact throughout implementations and post-go-live support. • Join client calls, lead technical discussions, and build trusted relationships with client stakeholders. • Respond quickly to client inquiries and issues while setting clear expectations on timelines and resolution paths. • Communicate complex technical concepts clearly and confidently to non-technical audiences. • Proactively surface client feedback and recurring issues to internal product and engineering teams. • Act as a first line of triage for issues raised by clients, Implementation, and Tech Support related to core integrations and digital banking workflows. • Independently investigate, analyze, and resolve issues before escalating to engineering. • Provide engineers with clear reproduction steps, impact analysis, and full context when escalation is required. • Coordinate closely across Implementation, Tech Support, QA, and Operations to close the loop on all reported issues. • Maintain a well-organized and prioritized JIRA backlog across multiple workstreams. • Write clear user stories, acceptance criteria, and supporting documentation. • Track delivery progress, dependencies, and follow-ups across projects. • Proactively identify risks and communicate updates to stakeholders. • Balance competing priorities across client-facing issues, integration delivery, and backlog management.