Sr. Director, Software Engineering

Flexi Software is seeking a hands-on, AI-forward engineering leader to establish and lead a second engineering practice focused on delivering our next-generation platform. This role reports to the CTO and involves hiring, setting technical direction, and shipping modern, web-based software while maintaining enterprise-grade security, reliability, and resilience for financial institutions.

About Flexi

Flexi Software has been a trusted provider of accounting solutions for over 30 years, specializing in cloud-based and on-premise software for organizations with complex accounting needs, including multi-entity and intercompany accounting at scale. Our suite includes modules like General Ledger, Accounts Payable, Accounts Receivable, Purchasing, Fixed Asset Management, Project Accounting, Workflow Automation, Financial Reporting, and Budget Software. We serve industries such as banking, insurance, financial services, credit unions, healthcare, and business process outsourcing, known for robust features, flexible deployment, and exceptional customer support.

In January 2025, Flexi was acquired by Quality Standard, a permanent capital holding company that invests in 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, while Quality Standard is headquartered in New York, NY.

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.
• Lead the team’s use of AI to accelerate delivery, embedding AI across coding, code review, testing, and documentation while maintaining high quality.
• Build on modern web-based technologies — JavaScript, HTML, React, Vite, and similar — backed by Microsoft SQL Server, with a focus on performance.
• Uphold enterprise standards for security, reliability, resilience, and data integrity expected by financial institutions.
• Partner with the CTO to define architecture standards, platform direction, and integration with Flexi’s existing C++/C# and DevOps environment.
• Establish engineering discipline from day one, including coding standards, testing, CI/CD, observability, and release practices.
• Manage cloud platforms and cloud spend, making sound build-versus-buy decisions to optimize cost without compromising scalability or security.
• Hire, onboard, and develop engineers, coaching them toward strong technical careers and identifying future leaders.
• Define and own engineering KPIs for 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 AI-forward engineering leader who has measurably accelerated delivery using AI tooling while protecting quality.
• Demonstrated ability to deliver software to the standards expected in regulated, high-trust environments (e.g., banking, insurance, financial services).
• 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 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 lead from inside the team, not above it.
• Aggressive and AI-forward; you actively use AI in your work and push your team to do the same, treating speed as a competitive advantage.
• Equally committed to rigor; you bring the discipline, security mindset, and reliability that financial-grade software demands.
• A builder; you are comfortable starting from zero — hiring, structuring, and setting 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 more enjoyable with people you like.

What Success Looks Like In The First 6 Months

• The second engineering practice is stood up — key hires made, the team structured, and an AI-forward way of working established.
• Engineering standards are 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 are delivered on the modern web stack, with performance measured and managed.
• AI is embedded in how the team works, with measurable gains in delivery speed at a high-quality bar.
• Clear architecture direction is agreed with the CTO, including how the new practice integrates with Flexi’s existing technologies and roadmaps.
• Cloud spend is understood and optimized.
• Engineering KPIs — velocity, reliability, performance, quality, and cost — are defined, baselined, and trending in the right direction.

Benefits

• Paid holidays and paid time off.
• 401(k) Plan with company participation.
• Health and dental insurance.
• Life and disability insurance.
• Vision discount plan.

Schedule

This is a hybrid position, working in-person with the CTO and team in our Atlanta, GA office.