Director/ VP of Engineering

Flexi•Atlanta, GA

4d•Hybrid

About The Position

Flexi Software is hiring a Director / VP of Engineering to stand up and lead a second engineering practice — an AI-forward team responsible for delivering the next-generation platform for our solutions. Reporting to the CTO, you will hire, set its technical direction, and ship modern, web-based software while holding to the enterprise standards of security, reliability, and resilience that the most mature financial institutions expect. This is a hands-on, player-coach role. You will be in the architecture and the code, not managing from a distance. We are looking for an aggressive, AI-forward engineering leader who uses AI to move fast — and who pairs that speed with the discipline and rigor our customers in banking, insurance, and financial services depend on. Both are required: we are not trading one for the other. The role can be filled at the Director or VP level depending on experience. This position is a hybrid position, working in-person with the CTO and team in our Atlanta, GA office. 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, products, and operations. Flexi’s offices are located in Shelton, CT and Atlanta, GA. Quality Standard is headquartered in New York, NY.

Requirements

Bachelor’s degree in software engineering, computer science, or a related technical field — or equivalent practical experience
10+ years in software engineering and architecture, with deep, current, hands-on coding ability — this is a player-coach role
5+ years leading technical teams, including direct experience hiring and building an engineering team from the ground up
Strong hands-on depth in modern web-based development — JavaScript, HTML, React, Vite, and related front-end technologies — and the APIs and services behind them
Solid experience with Microsoft SQL Server and a track record of building for application and database performance at scale
Proven, hands-on experience as an aggressive, AI-forward engineering leader who has measurably accelerated delivery using AI tooling, with a clear point of view on how to push velocity while protecting quality
Demonstrated ability to deliver software to the standards expected in regulated, high-trust environments — security, reliability, resilience, and data integrity (banking, insurance, financial services, or similar)
Strong technical depth across modern software architecture, cloud platforms, DevOps, and CI/CD; comfort integrating with existing C++/C# systems
Experience managing cloud platforms and cloud spend, including cost optimization and build-versus-buy decisions
Strong judgment in technical decision-making, cost tradeoffs, risk management, and execution planning
Excellent communication skills with executives, product leaders, engineers, and business stakeholders
Experience with ERP, accounting, financial, or other enterprise systems of record is highly desirable, especially B2B enterprise software

Nice To Haves

Experience with AWS and/or Azure, Containerization, Terraform, CI/CD, and observability platforms
Practical AI engineering experience — using LLMs, coding assistants, and agentic workflows to accelerate software delivery and, where valuable, to ship customer-facing capabilities
Strong software engineering background in C++, C#, TypeScript, Python, or similar
Experience with TDD, event-driven architecture, microservices, and platform engineering

Responsibilities

Stand up a second, AI-forward engineering practice — hire, structure, and lead the team responsible for delivering Flexi’s next-generation platform
Own delivery of the next-generation platform end to end, from architecture through development, QA, release, and ongoing operation
Operate as a hands-on player-coach: stay in the architecture and the code, contribute directly, review your team’s work, and lift the bar by example — not from a distance
Lead the team’s use of AI to accelerate delivery, embedding AI across coding, code review, testing, and documentation, and pushing aggressively for speed without sacrificing quality
Build on modern web-based technologies — JavaScript, HTML, React, Vite, and similar — backed by Microsoft SQL Server, with a strong focus on application and database performance
Hold the new practice to the enterprise standards expected of financial institutions: security, reliability, resilience, data integrity, and the controls our regulated customers depend on
Partner with the CTO to define architecture standards, platform direction, and how the new practice integrates with Flexi’s existing C++/C# and DevOps environment
Establish sound engineering discipline from day one — coding standards, testing, CI/CD, observability, and release practices — for a team being built from the ground up
Manage cloud platforms and cloud spend; make sound build-versus-buy decisions and optimize cost without compromising scalability, security, or reliability
Hire, onboard, and develop engineers; coach toward strong technical careers and identify the team’s future technical leaders
Define and own engineering KPIs around delivery velocity, system reliability, performance, quality, and cost efficiency
Partner closely with Product to turn the roadmap into shipped customer-facing software