Job Description

We're looking for a Senior Product Manager to own and evolve Cait, Candidly's AI-powered conversational financial wellness assistant. Cait helps users navigate student debt, college planning, and employer benefits through intelligent, personalized guidance. You'll define the product vision, drive the roadmap, and ship features that meaningfully improve financial outcomes for hundreds of thousands of users.

This role requires someone who is AI-enabled—you actively use AI tools (Claude Code, ChatGPT, Cursor, etc.) to accelerate your work, from writing specs to analyzing data to prototyping solutions. We expect you to bring a force-multiplier mindset: leveraging AI to move faster, think deeper, and ship better products.

What You'll Do

Product Strategy & Execution

• Define and own the vision, strategy, and roadmap for Cait across student debt, college planning, and benefits guidance for our enterprise customers
• Partner with engineering, design, and data science to ship enterprise-ready features iteratively
• Write clear briefs, specs, and user stories that align teams and reduce ambiguity
• Lead discovery and research—user interviews, data analysis, competitive landscape—to inform prioritization

AI-First Product Development

• Collaborate with the AI/ML team on agent engineering, tool design, RAG content strategy, and conversational design
• Design conversation flows, guardrails, and fallback logic for an LLM-powered assistant
• Use AI tools daily to accelerate your own workflows—drafting docs, analyzing metrics, synthesizing research, prototyping ideas
• Own the evals process: Define what "good" looks like for Cait's responses—accuracy, tone, compliance, actionability. Build and maintain test sets that catch regressions, measure quality over time, and give the team confidence to ship. You'll work with engineering to integrate evals into CI/CD so we can iterate on prompts and models without breaking things.

Metrics & Iteration

• Define KPIs and build dashboards to measure engagement, conversion, and user outcomes
• Run experiments (A/B tests, feature flags) and drive data-informed iterations
• Conduct funnel analysis and identify opportunities to improve activation, retention, and value delivery

Cross-Functional Collaboration

• Work closely with Customer Success, Support, and Compliance to incorporate feedback and ensure quality
• Partner with Sales and Marketing on positioning, demos, and go-to-market for new capabilities
• Communicate roadmap progress, launch results, and learnings across the org

Continuous Improvement

• Prioritize and manage the backlog; lead sprint ceremonies and release coordination
• Test releases, triage bugs, and maintain product quality standards
• Contribute to evolving our product culture, processes, and best practices

What We're Looking For

Experience

• 3-5 years as a Product Manager in B2C or B2B SaaS, with demonstrable experience shipping and iterating on successful AI-based products
• Experience with AI/ML-powered products—conversational AI, LLMs, recommendation systems, or similar
• Background in FinTech, ideally in financial wellness, lending, benefits, or personal finance
• Proven ability to define metrics, run experiments, and use data to drive decisions

Skills & Mindset

• AI-enabled: You actively use AI tools to multiply your productivity and expect the same from your teams. You're curious about what's possible and quick to adopt new capabilities.
• Strong analytical skills—comfortable with SQL, dashboards, and funnel/conversion analysis
• Excellent written and verbal communication; can write a crisp spec or tell a compelling product story
• Pragmatic decision-maker who balances user needs, technical feasibility, and business priorities
• Ownership mentality—you drive outcomes, not just outputs
• Collaborative and low-ego; you build trust across functions

Bonus

• Hands-on experience with AI evals—building test sets, defining rubrics, running automated and human evaluations, using tools like Braintrust, Langsmith, or custom frameworks
• Experience with prompt engineering, agentic, and RAG architectures
• Familiarity with student loans, IDR plans, PSLF, 529s, or employer benefits (SLRM, tuition reimbursement, etc.)
• Experience working directly with enterprise clients or B2B2C models

Why Candidly?

We're building the future of financial wellness—helping people tackle student debt, plan for college, and maximize their benefits. Cait is at the center of that mission: an AI assistant that delivers personalized, actionable guidance at scale. If you want to ship AI products that genuinely improve people's financial lives, this is the role.