Director of Product

This is a fully remote position, open to applicants in Connecticut.

📋 Description

• Collaborate with the CEO and CTO to craft and refine Flexi's product strategy, ensuring that roadmap priorities address both immediate customer needs and long-term enterprise value.

• Act as the main owner of roadmap recommendations and prioritization, working closely with the CEO and CTO to ensure product investments align with the company's strategy.

• Conduct continuous customer discovery to identify unmet needs, validate assumptions, and convert customer insights into product decisions.

• Regularly analyze the market—including competitors, adjacent tools, and category trends—and interpret findings to inform the roadmap.

• Engage in fieldwork: conduct on-site customer observations, attend meetings with customers and prospects, and accompany sales calls to witness real workflows firsthand.

• Collaborate with sales on active deals and perform win/loss analysis to inform positioning, prioritization, and roadmap decisions.

• Integrate market signals with technical opportunities and constraints to establish a well-supported viewpoint on what to build and why.

• Serve as the primary customer-facing product representative, gathering feedback, communicating upcoming changes, and managing expectations throughout the development cycle.

• Create comprehensive technical specifications, functional requirements, and user stories that engineering teams can utilize without further clarification.

• Work closely with the delivery organization throughout the build process—ensuring they have the necessary resources, eliminating ambiguity, and confirming that the final product effectively addresses customer needs.

• Direct product design decisions, using design tools or collaborating with external design resources to achieve high-quality UX outcomes.

• Oversee the entire product lifecycle, from discovery and specification to engineering delivery, QA, launch, and post-launch evaluation.

• Partner with sales and customer success teams to assist with deals, onboarding, and escalations that involve product elements.

• Develop and maintain product documentation, release notes, and internal training resources.

• Actively utilize AI in discovery, analysis, specification, design, and product development processes. Continuously assess new AI capabilities and identify ways to integrate them into both Flexi's internal operations and customer-facing products.

⛳️ Requirements

• Over 5 years of product management experience with substantial ownership of roadmap, customer discovery, and product strategy; a prior Director title is not necessary.

• Proven experience managing a complete product roadmap independently, without support from a PM team or dedicated design organization.

• Demonstrated capability to carry out structured customer discovery and translate raw insights into clear, prioritized product decisions.

• Familiarity with product design tools such as Figma or similar.

• Outstanding written and verbal communication abilities; you create specs, roadmaps, and customer communications that are engaging and well-received.

• Strong technical understanding, comfortable reviewing code, composing detailed specifications, and interacting directly with engineering on complex trade-offs.

• Experience with ERP, accounting systems, financial software, or other operational systems of record is highly desirable, particularly in B2B enterprise software solutions.

🏝️ Benefits

• Paid holidays and paid time off.

• A 401(k) Plan with company contribution.

• Health and dental insurance.

• Life and disability insurance.

• A vision discount plan.