Director of Software Engineering

Fortress Affinity Management is Higginbotham's standalone affinity insurance platform — purpose-built to turn group relationships into scalable, recurring insurance programs. FAM provides the complete infrastructure needed to support these programs, including digital intake systems, member portals, and dedicated service teams, all aimed at reducing friction and improving results for both producers and their clients.

Position Summary: The Director of Software Engineering leads day-to-day engineering execution for Fortress Affinity Management’s growing digital insurance platform. This player-coach owns delivery across software development, QA, and DevOps; establishes practical standards for architecture, code quality, security, and release reliability; and partners with business leaders to turn priorities into dependable outcomes. The role is designed for a technically credible leader who can guide a small, high-output team, review critical designs and pull requests, and improve the systems and practices that enable the team to scale.

This is an opportunity to shape engineering practices and platform direction in a business where technology has a direct, visible effect on client and member experiences. The successful candidate will have meaningful ownership, close access to business decision-makers, and the ability to improve how a focused team designs, builds, and operates products—without the layers and narrow scope common in much larger technology organizations.

Supervisory Responsibilities: Directly leads the software development, QA, and DevOps functions within Fortress’ IT group; specific team size and reporting relationships will be shared during the interview process.

Key Responsibilities

The role is best suited to a leader who values broad ownership and hands-on influence over building a large organization or managing through multiple layers. Success will be measured by predictable delivery, sound technical decisions, a healthy and accountable team, and steady improvement in product quality, security, and operational reliability.

Leadership

• Translate business priorities into a clear engineering roadmap and achievable delivery plans across active and upcoming projects, balancing client commitments, technical risk, and team capacity.

• Lead sprint planning, backlog prioritization, and delivery governance in Azure DevOps while improving predictability, visibility, and follow-through.

• Set and uphold practical standards for architecture, code quality, security, data, testing, and operability; stay close enough to critical designs and pull requests to evaluate quality firsthand and coach the team effectively.

• Partner with the product owner and business stakeholders to clarify priorities, shape requirements and acceptance criteria, and maintain a healthy backlog that reflects delivery capacity and business value — with product accountable for what is built and why, and engineering accountable for how it is built and when it lands.

• Surface delivery, timeline, technical, and resourcing risks early, with clear options and recommendations for leadership.

• Represent engineering in client-facing conversations about delivery commitments, dependencies, and technical trade-offs when needed.

Team & People Management

• Lead the performance, growth, workload, and engagement of the development, QA, and DevOps functions through clear expectations, regular feedback, coaching, and accountability.

• Recruit, onboard, and develop engineering talent, building repeatable practices that help new hires contribute quickly and sustainably.

• Establish and improve engineering operations across development, QA, and DevOps, including release discipline, service reliability, incident learning, security practices, and appropriate automation.

• Evaluate and guide the responsible use of AI-assisted development tools to improve engineering speed and quality while protecting source code, customer data, security, and review standards.

• Foster a culture of ownership, constructive challenge, quality, learning, and continuous improvement.

Core Competencies

• Leadership: Display leadership skills and ability to motivate fellow employees. Creates clarity, raises standards, develops people, and makes sound decisions in a small, high-output environment.

• Ability to Analyze and Solve Problems: Skill in recognizing challenges, exploring options, and implementing effective solutions in a timely manner

• Attention to Detail: A strong focus on completing tasks and projects accurately and thoroughly

• Communication and Influence: Explains technical choices, delivery risk, and trade-offs clearly to engineers, business stakeholders, executives, and clients, and builds alignment around decisions.

• Timely Task Completion: Ability to finish tasks and projects efficiently, managing resources and priorities effectively

• Team Collaboration: Willingness to work together with others, promoting teamwork and supporting shared goals

• Client Focus: Dedication to understanding and addressing the needs of clients and stakeholders to ensure their satisfaction

• Dependability: Acknowledgment of the importance of being present and punctual

• Creative Thinking: Openness to suggesting new ideas and methods to improve processes and outcome

• Organizational Skills: Capability to prioritize tasks and manage multiple projects simultaneously

• Technical Credibility: Evaluates architecture, design decisions, and critical code changes firsthand, asks effective technical questions, and provides clear guidance without becoming a bottleneck.

• Judgment and Problem Solving: Identifies root causes, weighs business and technical trade-offs, and moves the team toward practical, durable solutions.

• Accountability: Follows through on commitments, addresses delivery or quality concerns promptly, and creates clear ownership across the team.

• Adaptability: Responds constructively to changing priorities while protecting quality, team health, and long-term platform needs.

Experience & Education

• Demonstrated success leading a small software engineering team through competing priorities, improving delivery predictability and technical quality, and developing engineers through clear expectations, feedback, and coaching.

• Substantial software engineering experience, including several years of technical leadership with accountability for delivery and people management, required.

• Experience with Agile delivery practices and Azure DevOps work item management.

• Experience building multi-tenant SaaS products or software in insurance, financial services, healthcare, or another regulated-data environment is a plus.

• Experience evaluating and guiding the responsible use of AI-assisted development tools such as Claude Code, GitHub Copilot, or similar products.

• Bachelor’s degree in Computer Science, Information Technology, or a related field preferred; an equivalent combination of education and relevant experience will be considered.

Systems & Technical Skills

• Deep experience with modern application architecture, APIs, data access patterns, and relational databases is required. Current or recent hands-on familiarity with the platform stack — C#, ASP.NET Core, Entity Framework Core, and SQL Server — is strongly preferred. Experience with Blazor is helpful but not required.

• Azure DevOps experience across Boards, Repos, and Pipelines.

• Microsoft Azure experience across application hosting, identity and secrets management, observability, security, and high-availability and disaster-recovery design; experience with App Service and Key Vault preferred.

• Working knowledge of modern CI/CD, automated testing, production monitoring, and secure software delivery practices.

• Familiarity with Cloudflare and AWS-based tooling is a plus.

Physical Requirements

• Ability to lift 25 pounds

• Repeated use of sight to read documents and computer screens

• Repeated use of hearing and speech to communicate on telephone and in person

• Repetitive hand movements, such as keyboarding, writing, 10-key

• Walking, bending, sitting, reaching and stretching in all directions

Benefits & Compensation:

• Higginbotham offers medical, dental, vision, prescription drug coverage, 401K, equity incentive plan as well as multiple supplemental benefits for physical, emotional, and financial wellbeing.

• Employee Wellness Program

• Company paid holidays, plus PTO

Notice to Recruiters and Staffing Agencies: To protect the interests of all parties, Higginbotham Insurance Agency, Inc., and our partners, will not accept unsolicited potential placements from any source other than directly from the candidate or a vendor partner under MSA with Higginbotham. Please do not contact or send unsolicited potential placements to our team members.

*Applications will be accepted until the position is filled