Job Description

Technical Lead – Specialty Insurance & SQL Systems

Location: Chicago, IL (Hybrid)

Position Type: Full-time, Permanent

About Our Client

Leap Recruitment Partners has teamed up with a dynamic, rapidly growing industry leader in the wholesale insurance and specialty underwriting (MGA) space. Known for their collaborative culture and dedication to modernizing insurance technology, they are looking for a skilled technical champion to help shape the future of their core platforms.

On their behalf, we are seeking an energetic, solutions-oriented Technical Lead to join their team in Chicago on a hybrid schedule.

The Role

In this pivotal role, you will bridge the gap between business strategy and technical execution. You will act as the principal architect and hands-on guide for a dedicated team of software developers, quality engineers, and business analysts. If you have a deep understanding of specialty property and casualty (P&C) insurance operations and possess elite SQL capabilities, this is your opportunity to drive high-impact transformation initiatives.

Key Responsibilities

• Technical Direction: Serve as the primary technical authority, designing and deploying robust, scalable software solutions.

• Application Stewardship: Act as the single point of contact for the development, maintenance, and optimization of our current application ecosystem, including resolving critical production issues.

• Database Management: Oversee and optimize SQL database landscapes across development, testing, and live production environments.

• System Modernization: Champion transition strategies that migrate legacy applications to modern, cloud-friendly platforms without disrupting operational continuity or compromising data fidelity.

• Risk & Impact Analysis: Evaluate complex system architectures to identify vulnerabilities, assess operational risks, and formulate proactive mitigation plans.

• Collaboration & Partnership: Work alongside product owners and business executives to translate operational requirements into elegant technical specs.

• Team Mentorship: Serve as an active mentor and technical advisor to developers, cultivating best practices in coding, testing, and deployment.

• Documentation & Training: Produce clear technical guides and system documentation to streamline user training and operational handoffs.

What You Bring to the Team

Required Experience & Skills:

• Domain Expertise: A proven background in P&C specialty insurance (specifically managing general agent/MGA setups) and a firm grasp of premium accounting flows—including billing, cash collections, bordereaux generation, and financial reconciliation.

• SQL Mastery: 8 or more years of hands-on database development experience with deep expertise in SQL, SSIS, and ETL pipeline automation.

• Platform Exposure: Solid exposure to legacy and modern Policy Administration systems.

• Tooling & Ecosystem: Direct familiarity with systems such as Documaker, Rackley, Infomaker, PowerBuilder, Retool, GoAnywhere, Redgate tools, and Git.

• Modern Architecture: A strong understanding of cloud-managed services, service-oriented architecture (SOA), APIs, microservices, containerization, and modern web applications.

• Agile Mindset: Practical experience working in Agile (Scrum/Kanban) environments, utilizing tools like Jira, Confluence, and ServiceNow/ITIL frameworks.

• Soft Skills: Exceptional problem-solving capabilities, clear communication, and the ability to thrive both as an independent driver and a collaborative teammate.

Preferred Assets:

• Familiarity with cloud platforms (specifically Microsoft Azure or Google Cloud Platform).

• Experience with ConceptOne, AIM, or ImageRight platforms.

Why Apply?

This is a chance to work on high-value modernization projects where your voice and technical guidance will directly influence business outcomes. Our client offers a competitive compensation package, excellent benefits, and a highly collaborative hybrid work model in the heart of Chicago.

At Leap we are an Equal Opportunity and Affirmative Action Employer. That means all applicants will be considered for employment without attention to race, color, religion, sex, sexual orientation, gender identity, national origin, veteran, or disability status. Leap will not tolerate any discrimination or harassment based on any of these characteristics. Leap encourages applicants of all ages.