Company Description

Candidly was founded in 2016 to flip the script on what it means to plan, borrow, repay, and save for college. Today, we’re the category leader with the market’s most comprehensive AI-driven student debt and savings optimization platform. We partner with hundreds of top employers, financial institutions, and retirement record keepers, positioning Candidly to serve more than 35 million Americans.

We’re already achieving incredible results — to date, we’ve helped our users get on track to eliminate more than $1.8B in student debt and pay off their loans 175,000 years quicker — and we’re seeking movers, shakers, innovators, and problem solvers to help take our mission even further.

Candidly is a high-growth, Series B startup, funded by leading investors including Altos Ventures, Aflac, Salesforce Ventures, UBS, Equal Opportunity Ventures, Impact Engine, Rethink Impact, Unum, and Cercano Management. Our fully remote, international team of 70 (and counting) includes alumni from Google, UBS, Twitter, Plaid, Prudential, LendingTree, Morgan Stanley, Deutsche Bank, and more.

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.

Background and EEOC

Candidly offers for employment are conditioned upon satisfactory completion of our employment screening process (including, but not limited to, a review of past employment and education records, background investigation, and/or credit check & fingerprints).

Candidly strives to foster an environment where every employee can succeed. As an Equal Opportunity Employer we do not discriminate on the basis of race, religion, color, sex, sexual orientation, gender identity, gender expression, national origin, age, non-disqualifying physical or mental disability, veteran status, or any other basis covered by applicable law. All employment is decided on the basis of qualifications, merit, and business need.

Senior Product Manager, Cait

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