About Loggerhead Risk Management LLC Loggerhead is a property and casualty insurer that specializes in providing coverage that meets the unique needs of Florida homeowners. We’re a team of insurance professionals with customer service as our core value, and we understand the importance of providing attentive service to our policyholders. Loggerhead is powered by modern technology, guided by people who share a commitment to trust, empathy, always doing what’s right, flexibility, and teamwork.

Role Overview The Software Development Manager is a hands-on technical leader responsible for leading a small, high-performing team while actively contributing to the design, development, and delivery of modern software solutions. This role is ideal for a passionate builder and mentor—someone who remains deeply engaged in coding, system design, and emerging technologies while guiding developers toward best practices and high-quality outcomes. Success requires active participation in development, code reviews, troubleshooting, and technical decision-making alongside leadership responsibilities.

Key Responsibilities

Hands-On Engineering & Architecture.

Actively design, develop, and maintain production-grade software (backend and frontend).

Contribute directly to complex feature development and system enhancements.

Lead architectural decisions for microservices-based systems.

Guide evolution of cloud-native applications in Azure (AKS, APIM, CosmosDB)

Enforce clean architecture, coding standards, and performance best practices

Technical Leadership & Mentorship

Lead and mentor a team of 6 resources across Software Development and DevOps

Provide hands-on coaching through code reviews and pair programming

Promote engineering excellence, accountability, and continuous improvement

Establish secure coding practices and strong testing discipline

Delivery & Business Alignment





Translate business requirements into scalable technical solutions

Support delivery of customer-facing digital products

Align engineering efforts with customer experience and business goals

AI & Modern Development Practices

Identify and implement AI use cases for developer productivity and customer experience

Drive adoption of CI/CD, test automation, and observability practices

DevOps & Platform Oversight

Oversee CI/CD pipelines and DevOps practices

Partner with DevOps to improve deployment reliability and scalability.

Required Qualifications

10+ years software development experience with robust hands-on coding

3+ years in a technical leadership role

Expertise in Java and Spring Boot

Experience with microservices and REST APIs

Strong knowledge of NoSQL (CosmosDB, MongoDB) and JSON

Experience with JavaScript/TypeScript frontend frameworks

Experience with container technologies, preferably Kubernetes (AKS)

CI/CD and DevOps practices with Git-based workflows

Experience building externally facing web applications

Strong secure coding practices

Preferred Qualifications

Experience in P&C; insurance or financial services

Familiarity with AI/ML applied to business workflows

Experience scaling high-transaction systems

Core Competencies

Hands-on leadership and mentorship

Strong problem-solving skills

Ability to align business and technology

Pragmatic and results-driven mindset

Commitment to innovation, quality, and continuous improvement

ADA: The above statements cover what are generally believed to be the principal and essential functions of this job. Specific circumstances may allow or require some people assigned to the job to perform a somewhat different combination of job duties.

Job Type: Full-time

Benefits:

401(k)

Dental insurance

Health insurance

STD/LTD

Life Insurance

Paid time off

Vision insurance

Referral Program

Tuition Reimbursement

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📌 Software Development Manager (Winnipeg)
🏢 Visa Hunt
📍 Winnipeg