Director, Product Management

Description

Flexi Software is seeking its first Director of Product, a founding product leader who will build and own the entire product function from the ground up. This is a rare opportunity to define how product is done at a 30-year-old company in the middle of a meaningful modernization. The Director of Product will own the roadmap, drive customer discovery, write technical specs, shape product design, and partner directly with the CEO and CTO on strategy. Crucially, you will be Flexi’s eyes and ears on the market — continuously scanning competitors, talking to customers and prospects, sitting in on sales calls, and observing how the work actually gets done — then blending what you learn with technical opportunity and constraints to decide what we build. There is no team to inherit and no existing PM structure to slot into. You will create it.

This role is ideal for someone who has operated as the sole product person before, or who has the judgment, initiative, and ambition to do so for the first time. You will be embedded in every corner of the business: talking to customers, sitting in engineering standups, reviewing support escalations, and presenting roadmap updates to the executive team. The breadth is intentional. At Flexi, the Director of Product is not a coordinator; they are a force multiplier.

This is a remote-eligible role, with a preference for candidates who can travel regularly (6–10 times a year) to visit customers, attend industry events, and work in-person with the CEO and team as needed. Preference for candidates based in or near Shelton, CT or Atlanta, GA.

About Flexi

Flexi Software has been a trusted provider of accounting solutions for over 30 years, offering both cloud-based and on-premise software purpose-built for organizations with the most complex accounting requirements — multi-entity and intercompany accounting at scale. Our comprehensive suite includes modules like General Ledger, Accounts Payable, Accounts Receivable, Purchasing, Fixed Asset Management, Project Accounting, Workflow Automation, Financial Reporting, and Budget Software. Serving industries including banking, insurance, financial services, credit unions, healthcare, and business process outsourcing, Flexi is renowned for its robust features, flexible deployment options, and exceptional customer support.

In January 2025, Flexi was acquired by Quality Standard, a permanent capital holding company that acquires and grows software businesses with a long-term ownership mindset. Quality Standard is actively investing in Flexi’s people, product, and operations.

Flexi’s offices are located in Shelton, CT and Atlanta, GA. Quality Standard is headquartered in New York, NY.

Roles and Responsibilities

• 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-l…