Candidly

• Lead the design and implementation of scalable, secure, and resilient cloud infrastructure across AWS and Azure, supporting both Candidly's AI and SaaS products • Drive the architectural vision and strategy, ensuring alignment with long-term business goals and surfacing risks before they become problems • Own and enforce best practices for infrastructure as code (IaC), CI/CD, and automated deployments • Take the lead on automating and accelerating SDLC processes — identifying bottlenecks in how we build and ship, and designing solutions that make the whole pipeline faster and smoother, whether that involves AI-assisted tooling or traditional automation • Serve as a subject matter expert on cloud architecture, containerization, and observability • Lead incident response and post-mortems with a focus on systemic improvement, not just immediate fixes • Proactively identify and close gaps before they compound.

• Own the vision, strategy, and roadmap for how Candidly delivers its platform to employers at scale. • Define and improve the systems that power employer onboarding. • Partner with engineering to build scalable, repeatable delivery infrastructure that reduces implementation time and manual effort. • Write clear briefs, specs, and user stories that align teams and reduce ambiguity. • Design and optimize delivery workflows end-to-end. • Build and maintain delivery playbooks that enable Customer Success to activate new employers. • Establish SLAs, tracking, and reporting for delivery timelines across partner channels. • Drive continuous improvement in delivery velocity.

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 lead our Delivery pod, the team responsible for getting the Candidly platform into the hands of employers and their employees as quickly and cost-efficiently as possible. This team owns the core infrastructure that powers employer onboarding, census management, HRIS integrations, SSO configurations, and partner-specific platform delivery. You'll define how we scale our delivery engine from high-touch enterprise implementations to streamlined, self-service SMB launches — all while maintaining the reliability and compliance our financial institution partners require. This is a B2B2C role. Our partners are large financial institutions and retirement recordkeepers (think Vanguard, Bank of America, Lincoln Financial, Empower). They distribute Candidly to their employer clients, who in turn serve their employees. You need to understand that full chain and build systems that work at every layer. 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 - Own the vision, strategy, and roadmap for how Candidly delivers its platform to employers at scale — from enterprise partners like Bank of America to SMB customers launching through self-service flows - Define and improve the systems that power employer onboarding: census file processing, SFTP/API configurations, HRIS integrations, SSO deployment, and program design templates - Partner with engineering to build scalable, repeatable delivery infrastructure that reduces implementation time and manual effort - Write clear briefs, specs, and user stories that align teams and reduce ambiguity Process & Systems Thinking - Design and optimize delivery workflows end-to-end — from signed contract to live employer, identifying bottlenecks and eliminating manual handoffs - Build and maintain delivery playbooks that enable Customer Success to activate new employers with minimal engineering involvement - Establish SLAs, tracking, and reporting for delivery timelines across partner channels (enterprise, mid-market, SMB) - Drive continuous improvement in delivery velocity: measure cycle times, identify failure points, and implement systemic fixes AI-First Product Development - Identify and ship AI-driven capabilities that accelerate delivery — census verification, automated configuration, onboarding assistants - Use AI tools daily to accelerate your own workflows and collaborate with engineering to build AI into the delivery pipeline Metrics & Iteration - Define and track delivery KPIs: time-to-launch, on-time delivery rate, employer satisfaction, cost per implementation - Run experiments to improve onboarding conversion, activation rates, and employer NPS Cross-Functional Collaboration - Coordinate across Customer Success, Partner Success, Sales, and Compliance to manage concurrent partner launches and meet financial institution security standards Continuous Improvement - Prioritize and manage the backlog; lead sprint ceremonies, release coordination, and product quality standards What We're Looking For Experience - 3-5 years as a Product Manager in B2B or B2B2C SaaS, ideally at a platform that serves enterprise financial institutions - Demonstrated experience building and scaling operational systems, delivery pipelines, or implementation infrastructure - Track record of reducing manual processes through automation, tooling, and workflow design - Experience managing complex, multi-stakeholder delivery timelines with external partner dependencies - Background in FinTech, benefits administration, HR tech, or financial services preferred Skills & Mindset - AI-enabled: You actively use AI tools to multiply your and your team’s productivity. You're curious about what's possible and quick to adopt new capabilities. - Process-oriented: You see messy workflows and can't help but systematize them. You think in terms of throughput, cycle time, and scalability. - Strong analytical skills — comfortable with SQL, dashboards, and operational metrics - Excellent written and verbal communication; can write a crisp spec or present delivery status to a partner executive - Pragmatic decision-maker who balances partner needs, technical feasibility, and business priorities - Ownership mentality — you drive outcomes, not just outputs - Collaborative and low-ego; you build trust across functions Bonus - Experience with census/employee data management, HRIS integrations (Workday, ADP, BambooHR), or SFTP/API-based data pipelines - Familiarity with employer benefits platforms, student loans, or SECURE 2.0 retirement matching - Experience with self-service onboarding or product-led implementation motions - Hands-on experience applying AI to operational workflows (not just consumer-facing features) - Experience working directly with enterprise financial institution partners or in regulated environments Why Candidly? We're building the future of financial wellness — helping people tackle student debt, plan for college, and maximize their benefits. The Delivery pod is the engine that makes it all real: every employer we launch, every employee we reach, starts here. If you want to build systems that scale impact and move fast in a mission-driven company, 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.

• Personally source and build pipeline through consistent, high-quality outbound activity • Execute targeted outbound motions across priority accounts and buyer personas • Partner with Marketing and Partnerships, but do not rely on inbound • Maintain sufficient pipeline coverage to support predictable closes • Lead complex, high-value sales cycles from first touch through close • Navigate executive buying committees and multi-stakeholder decision processes • Build clear business cases and ROI narratives • Own procurement, legal, security, and contracting workflows end-to-end • Close fewer, larger, more complex deals with discipline and follow-through • Maintain exceptional CRM hygiene, pipeline visibility, and forecast accuracy • Run structured deal processes with clear next steps and accountability • Collaborate cross-functionally to move deals forward • Model best-in-class execution and professionalism

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.

• Personally source and build pipeline through broker relationships and broker-led opportunities • Prospect, recruit, and activate new broker partners • Execute targeted outbound motions to brokers and broker-led employer opportunities • Lead broker-influenced and broker-sourced sales cycles from first touch through close • Run discovery, demos, and deal strategy with brokers and employer sponsors • Build trusted, long-term relationships with brokers and producing advisors • Maintain exceptional CRM hygiene, broker attribution, pipeline visibility, and forecast accuracy

• Design, build, and deploy AI Agents including custom tools, prompt engineering, orchestration workflows, and agent design patterns. • Design evaluation strategies and metrics for assessing the efficacy of AI agents as well as identifying common failure modes. Ensure AI agents and systems are reliable and provide a good user experience. • Contribute to the backend infrastructure powering Candidly's AI capabilities, including API development, data integrations, and data pipelines. • Stay on the cutting edge of advancements in Generative AI space and evaluate new techniques for application within the Candidly AI platform. • Work closely with stakeholders across product, design, engineering, and leadership to translate complex AI concepts into actionable strategies and features. • Present findings and insights in a compelling way to both technical and non-technical audiences, contributing to strategic decision-making.

• Define and own the vision, strategy, and roadmap for Cait • Collaborate with engineering, design, and data science to ship features • Execute experiments and drive data-informed iterations • Design conversation flows and define KPIs