About the RoleLender Toolkit is looking for a VP of Product to own our product roadmap and drive the strategy behind how we plan, prioritize, and ship. This is a hands-on role. You'll be close to the work, not just steering from a distance. You'll partner directly with our in-house Mortgage Solutions experts and Engineering to turn deep industry knowledge and technical capability into a roadmap that's realistic, well-sequenced, and tied to clear deployment timelines. What you need is strong product instincts, the discipline to build and manage a roadmap, a thoughtful approach to AI, and the leadership to bring engineering, subject-matter experts, and support together around a shared plan.
What You'll DoRoadmap & Strategy- Own the end-to-end roadmap, balancing customer-driven features, legacy platform modernization, technical debt reduction, and AI-powered capabilities across platform, AI agents, document automation, integrations, and customer-facing workflows.
- Set and communicate product deployment timelines, working closely with Engineering to keep plans realistic, visible, and aligned with business priorities.
- Run regular roadmap reviews with leadership, explaining priorities, trade-offs, and sequencing in terms of customer value, business goals, and technical health.
- Treat technical debt and modernization as a visible, executive-level part of product planning, not a background engineering concern.
- Build roadmap themes such as AI-powered loan review, mortgage document intelligence, workflow automation, integration reliability, and reduction of manual work across lending operations.
Responsible AI & Governance- Identify where AI and automation can meaningfully reduce manual work, improve accuracy, or differentiate our product, and define how we'll measure it, including adoption, accuracy, time saved, ticket reduction, and revenue impact.
- Introduce AI features thoughtfully, with attention to user trust, data quality, explainability, security, privacy, vendor dependency, and compliance-sensitive workflows.
- Ensure AI-enabled initiatives go through appropriate review for the regulated, data-sensitive environment we operate in.
Cross Functional Partnership- Partner closely with internal mortgage solutions experts to ground product decisions in real industry, workflow, and regulatory context.
- Work side by side with Engineering on scoping, sequencing, and trade offs, staying hands on enough to understand the reasoning behind technical constraints.
- Act as the connective tissue between domain expertise, engineering capability, support insights, implementation realities, and go to market priorities.
- Build stronger feedback loops between customers, Support, Sales, Implementation, and Engineering.
- Use support trends, recurring issues, and implementation feedback as direct input into roadmap prioritization.
Product Execution- Stay involved in the details, including reviewing requirements, refining specs, attending key engineering syncs, validating release scope, and getting hands-on when needed.
- Define and track success metrics for major releases, modernization initiatives, and AI-enabled features.
- Build lightweight, repeatable processes for how product work is discovered, scoped, shipped, and measured, maturing our product discipline without adding unnecessary overhead.
- Use Azure DevOps for roadmap, backlog, and release management, and Lucidchart or Lucidspark for workflow mapping and product discovery. Microsoft 365 for day-to-day collaboration.
What We're Looking For- 10+ years in product management, including people leadership experience.
- Track record of owning a product roadmap and driving products from concept through deployment in a B2B SaaS environment.
- Experience leading product strategy for an established product, especially with legacy systems, technical debt, or complex integrations.
- Experience partnering closely with Engineering on scoping, timelines, and trade offs, comfortable in the technical weeds.
- Demonstrated ability to identify where AI, automation, or data can improve product value and efficiency, with a thoughtful, responsible approach to how AI features get introduced.
- Strong prioritization instincts and the ability to say no to good ideas in favor of the right ones.
- Excellent communication skills, with the ability to translate between technical, commercial, customer, and domain expert perspectives.
- A practical, low ego leadership style with a bias toward clarity, accountability, and execution.
- Comfortable in a fast-moving, evolving company where priorities can shift and you may need to wear multiple hats.
What Will Set You Apart- Background in mortgage, lending, fintech, banking, or another regulated, workflow-heavy industry. Not required, we have deep in-house expertise to lean on.
- Experience with document automation, OCR, data extraction, rules engines, or AI agents.
- Experience with enterprise customers, implementation teams, or compliance-sensitive product environments.
- Experience helping a company modernize from legacy systems toward a more scalable, cloud-based, AI-enabled architecture.
#BS-1
