Director of Product

Flexi Software

Director of Product at Flexi Software, leading product strategy and roadmap development in a remote role. Engaging deeply with customers and the engineering team for product lifecycle management.

Posted 6/19/2026full-timeRemote • Connecticut • 🇺🇸 United StatesLead💰 $150,000 - $190,000 per yearWebsite

Tech Stack

Tools & technologies

ERP

About the role

Key responsibilities & impact

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

What you’ll need

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

Comp & perks

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

ATS Keywords

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Applicant Tracking System Keywords

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Hard Skills & Tools

product managementroadmap ownershipcustomer discoverytechnical specificationsfunctional requirementsuser storiesUX designAI integrationcode reviewB2B enterprise software

Soft Skills

communication skillscollaborationcustomer-facingproblem-solvingleadershipanalytical thinkingprioritizationcustomer insight translationambiguity removalstakeholder management