Director of Digital Product at Watercress Financial Group LLC – Des Moines, Iowa

The Director of Digital Product is an execution-focused role, responsible for shaping, driving, and operationalizing the product vision across Watercress Group’s contractor experience and digital platform ecosystem. As a key member of the team, this role partners closely with Engineering, Compliance, Commercial, and Contractor Experience teams, amongst other stakeholders, to define and deliver a cohesive roadmap that accelerates value for contractors, borrowers, and platform partners.

This individual will translate business strategy into a clear, outcome-driven product direction; grounded in user research, data insights, and market needs while ensuring flawless execution across multiple workstreams. The Director of Digital Product will steward the evolution of our digital experiences, internal tools, and partner integrations, enabling scale, efficiency, and best-in-class journey design for all contractor users.

RESPONSIBILITIES

Product Strategy & Roadmap Leadership

• Own the multi-year product roadmap for contractor-facing and internal operational experiences, ensuring alignment with company priorities, revenue goals, and platform strategy.
• Translate business outcomes into clear product requirements, user stories, and acceptance criteria.
• Maintain a rigorous prioritization framework balancing customer needs, partner requirements, regulatory constraints, and development capacity.
• Drive the definition of product-market fit and performance standards for new digital capabilities.

Contractor Experience & Market Insight

• Serve as a subject matter expert on contractor workflows, pain points, motivations, and industry trends.
• Leverage Voice of Contractor research and integrate insights into product decisions.
• Build competitive intelligence around home improvement financing, digital application flows, and field-sales tooling to inform differentiation.
• Partner closely with cross-functional teams to ensure the product roadmap directly supports onboarding, sales enablement, performance, and operational scalability.

Execution & Delivery

• Lead cross-functional teams through discovery, design, development, and release cycles with a clear focus on measurable outcomes.
• Ensure high-quality product requirements, user journeys, and handoffs that enable Engineering to build efficiently.
• Partner with delivery teams to drive intuitive UX patterns and consistent interaction models across the contractor lifecycle.
• Collaborate with QA and Engineering to uphold release quality, reliability, and performance standards.

Operational Excellence

• Establish repeatable product operating rhythms including backlog refinement, sprint planning, release planning, and cross-team prioritization.
• Track and report product KPIs, including adoption, engagement, operational throughput, and financial impact.
• Ensure readiness for go-to-market, training, documentation, and communications in partnership with Marketing and Enablement.
• Champion user-centered product practices and data-driven decision making across the organization.

Cross-Functional Leadership

• Partner with Sales and Account Management teams, Marketing, and Contractor Support to ensure product strategy directly supports field performance and key business outcomes.
• Collaborate with Engineering leadership on capacity planning, sequencing, and technical tradeoffs.
• Act as a stakeholder for platform partnerships and integrations, defining requirements that expand functionality and contractor value.
• Serve as a connector between strategy, execution, and frontline feedback loops.

QUALIFICATIONS

• Bachelor's degree in Business, Finance, Engineering, or a related field; advanced degree or relevant certifications (e.g., in project management or UX design) preferred.
• Strong understanding of user-centered design, workflow mapping, and customer research methodologies.
• Experience working closely with engineering teams using Agile delivery models.
• Exceptional written and verbal communication skills with the ability to influence cross-functionally and at the executive level.
• Proven ability to align technical and non-technical stakeholders around a clear product direction.
• Experience in fintech, home improvement, contractor enablement, marketplace ecosystems, lending, RevOps, or similar environments preferred.

KNOWLEDGE AND SKILLS

• Strong technical fluency across integrations, digital workflows, and portal-based user experiences, with the ability to translate complex requirements into clear, actionable product direction.
• Deep user empathy and comfort leading discovery—distilling contractor needs, behavioral insights, and feedback into intuitive, impactful product solutions.
• Exceptional communication and cross-functional alignment skills, ensuring clarity across engineering, commercial, executives, and external partners.
• Proven ability to prioritize, manage roadmaps, and drive execution in fast-paced environments using tools like Jira, CRM systems, and product analytics platforms such as Jira.