Director of Product

Job not on LinkedIn

🕒 June 19

🦌 Connecticut – Remote

🦌 Connecticut – Remote

💵 $150k - $190k / year

⏰ Full Time

🔴 Lead

✅ Product Manager

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Flexi Software

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 1993

💼 Consulting

🏥 Healthcare

🛡️ Insurance

Consulting • Healthcare • Insurance

Flexi Software is a provider of comprehensive accounting software solutions for businesses with complex accounting needs, offering products that support multi-entity accounting, financial management, and accounting automation. The company's software is used by various industries including banking, insurance, financial services, healthcare, and more, and is recognized for its ability to efficiently handle billions of transactions and provide robust reporting and analytics capabilities. Flexi is committed to delivering flexible and scalable accounting solutions, making it suitable for both on-premise and cloud environments. With a focus on adaptability and integration, Flexi aims to meet the evolving needs of its customers worldwide.

📋 Description

• Partner with the CEO and CTO to develop and evolve Flexi's product strategy, ensuring roadmap priorities reflect both near-term customer needs and long-term enterprise value • Serve as the primary owner of roadmap recommendations and prioritization, partnering closely with the CEO and CTO to align product investments with company strategy • Conduct ongoing customer discovery to surface unmet needs, validate assumptions, and translate customer insight into product decisions • Continuously scan the market — competitors, adjacent tools, and category trends — and translate findings into clear roadmap implications • Get into the field: on-site customer observation, customer and prospect meetings, and riding along on sales calls to see real workflows firsthand • Partner with sales on active deals and run win/loss analysis to feed positioning, prioritization, and roadmap • Blend market signal with technical opportunity and constraints to form a defensible point of view on what to build and why • Serve as the primary customer-facing product voice, gathering feedback, communicating upcoming changes, and managing expectations through the development cycle • Write detailed technical specifications, functional requirements, and user stories that engineering can act on without translation • Partner hands-on with the delivery organization throughout the build — ensuring they have what they need, removing ambiguity, and verifying that what ships actually solves the customer’s problem • Lead product design decisions, working directly in design tools or with external design resources to produce high-quality UX outcomes • Manage the full product lifecycle, from discovery and spec through engineering delivery, QA, launch, and post-launch review • Collaborate with sales and customer success to support deals, onboardings, and escalations that have a product dimension • Build and maintain product documentation, release notes, and internal training materials • Leverage AI aggressively across discovery, analysis, specification, design, and product development workflows. Continuously evaluate emerging AI capabilities and identify opportunities to incorporate them into both Flexi's internal operations and customer-facing products.

🎯 Requirements

• 5+ years of product management experience with significant ownership of roadmap, customer discovery, and product strategy. Previous Director title is not required. • Experience owning a full product roadmap independently, without a supporting PM team or dedicated design organization. • Demonstrated ability to conduct structured customer discovery and translate raw insight into clear, prioritized product decisions • Familiarity with product design tools (Figma or equivalent) • Exceptional written and verbal communication skills; you write specs, roadmaps, and customer comms that people actually read • Strong technical acumen, comfortable reviewing code, writing detailed specs, and engaging directly with engineering on complex tradeoffs • Experience with ERP, accounting systems, financial software, or other operational systems of record is highly desirable, especially B2B enterprise software solutions.

🏖️ Benefits

• paid holidays and paid time off • a 401(k) Plan with company participation • health and dental insurance • life and disability insurance • a vision discount plan