Senior Director OF Software Engineering

Description

Flexi Software is hiring a Sr. Director, Software 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.

Roles and 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

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

Preferred Qualifications

• 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

Personal Characteristics

• Hands-on by nature; you are happiest closest to the work and lead from inside the team, not above it
• Aggressive and AI-forward; you actively use AI in your own work, push your team to do the same, and treat speed as a competitive advantage
• Equally committed to rigor; you bring the discipline, security mindset, and reliability that financial-grade software demands, and you don’t see that as at odds with moving fast
• A builder; you are comfortable starting from zero - hiring, structuring, and setting the standards for a brand-new team
• Strong technical judgment under ambiguity; you form a clear point of view and make decisions with imperfect information
• A developer of people; you genuinely enjoy coaching engineers and growing the next generation of technical leaders
• Collaborative and low ego; you earn trust across engineering, product, and the executive team
• High integrity and sound judgment; trusted with sensitive architecture, security, customer, and cost information
• Positive attitude and sense of humor; work is way more fun with people you enjoy!

What Success Looks Like in the First 6 Months

• The second engineering practice stood up - key hires made, the team structured, and an AI-forward way of working established
• Engineering standards in place from the start - coding standards, testing, CI/CD, observability, and security practices the team follows
• Meaningful, working increments of the next-generation platform already delivered on the modern web stack, with performance measured and managed
• AI embedded in how the team works, with measurable gains in delivery speed at a high-quality bar
• Clear architecture direction agreed with the CTO, including how the new practice integrates with Flexi’s existing technologies and their roadmaps
• Cloud spend understood and optimized
• Engineering KPIs - velocity, reliability, performance, quality, and cost - defined, baselined, and trending in the right direction

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:

Hybrid • Atlanta, GA area only

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