Director, Product Management

Job Description

Job Description

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-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

Personal Characteristics

• Proactive, self-directed, and capable of owning an entire product function end-to-end; you don't need a team around you to be effective
• High integrity, sound judgment, and trusted with sensitive roadmap, customer, and competitive information
• Decisive under ambiguity; you can form a strong point of view with imperfect information and move forward
• Genuine curiosity about AI and emerging technologies; actively uses AI tools in your product workflow and helps the broader team do the same
• Collaborative and low ego; you earn trust and influence from engineering, sales, and customers without relying on formal authority
• Deeply customer-empathetic; you build products that solve real problems, not just interesting ones
• Comfortable with the full spectrum of product work, from high-level strategy to writing a spec for a very specific edge case
• Positive attitude and sense of humor; work is way more fun with people you enjoy!

What Success Looks Like in the First 12 Months

• Establish a repeatable product discovery and roadmap process 
• Develop trusted relationships with key customers and partners 
• Deliver a prioritized roadmap aligned with customer needs and business objectives 
• Improve the quality and clarity of product requirements and engineering handoffs 
• Introduce product metrics and feedback mechanisms to guide decision-making 
• Identify and begin executing strategic modernization and AI initiatives

Flexi provides excellent benefits including paid holidays and paid time off, a 401(k) Plan with company participation, health and dental insurance, life and disability insurance, and a vision discount plan. 

  Location : Remote-Eligible • Preference for Shelton, CT or Atlanta, GA

Only candidates under consideration will be contacted. Any offer of employment will be contingent upon positive criminal background check.

No phone calls, please. Principals Only. Drug-free workplace. M/F/V/H EEO