Job Opportunity at We Insure Group
At We Insure Group, we are passionate, driven, and purposeful in our mission to personalize protection at the right value. We believe in delivering tailored insurance solutions that meet each client's unique needs, ensuring they feel confident and supported in every decision.
As both a franchise platform and direct insurance provider, We Insure empowers like-minded entrepreneurs with the opportunity to own and operate successful agencies. With over 200 locations across 35 states, we support our agency owners, customers, and carrier partners by enabling faster service, greater efficiency, better choices, and improved results.
What sets us apart? We're data-driven for better value and people led for better service. Our purpose is rooted in clarity, guidance, and long-term trust helping individuals and business owners make informed choices about their insurance coverage. We're building something meaningful and looking for purpose-driven individuals to help lead the way.
Key Responsibilities
Technology Strategy & Roadmap
- Develop and refine a technology modernization roadmap in alignment with business goals.
- Identify opportunities to leverage technology for efficiency, better customer experience, and competitive differentiation.
- Present strategy and updates to executive leadership and company ownership.
Project Leadership
Lead end-to-end execution of technology projects from quick-win automations to long-term platform implementations.Prioritize and manage a portfolio of initiatives (system integrations, software development, vendor implementations) using agile best practices.Ensure projects are delivered on time and within budget.Systems Integration & Architecture
Oversee the integration of our core systems (Applied Epic AMS, InsuredMine CRM, comparative raters, telephony, data warehouse, etc.).Design and implement a cohesive architecture that reduces data silos e.g., integrating via APIs and middleware.Take ownership of data flow and accuracy across platforms.Software Development & Automation :
Architect and develop cloud-native tools to fill gaps not met by vendors. Examples : build lightweight web applications for agents (unified portal / dashboard), automation scripts or RPA bots for repetitive tasks, custom reporting solutions, and potentially customer-facing apps / portals. Ensure solutions are secure, scalable, and maintainable.Vendor Management
Act as the primary liaison with key technology vendors (Applied Systems, etc.).Evaluate third-party solutions and negotiate contracts / pricing in collaboration with procurement. Ensure we are fully leveraging vendor capabilities and also holding them accountable to support our needs (for example, advocating for API enhancements or better franchise-specific features).Cloud Infrastructure & Security
Oversee our cloud infrastructure (primarily AWS) and ensure reliability and security of all systems.Coordinate with any IT / security resources to implement appropriate data protection, backups, and cybersecurity measures (MFA, encryption, compliance with insurance data regulations). Though we have vendor-hosted systems, you will ensure our integrated environment meets high availability standards.Metrics & Reporting
Define and track key performance indicators (KPIs) for technology operations e.g., project ROI, adoption rates of new tools, system uptime, response times, etc.Provide transparent updates to leadership and franchisees on tech improvements (for instance, monthly summary of efficiencies gained). Use data to drive decision-making and continuous improvement in the tech team.Qualifications
Experience :
7+ years in software engineering / IT roles with at least 3+ years in a technology leadership or engineering manager position.Insurance industry experience strongly preferred familiarity with insurance agency management systems, comparative raters, or fintech in a regulated environment will be a big plus.Technical Skills :
Proven full-stack development capabilities (e.g., proficiency in a programming language such as Python, C# or Java, and web technologies like JavaScript / Node, Angular or React).Experience with RESTful APIs (JSON) including integrating 3rd-party services.Cloud expertise (AWS or Azure) in deploying applications and using cloud services.Comfort with databases and data modeling (SQL, possibly Snowflake or similar). Some experience with RPA tools or scripting for automation is a plus.Strategic Thinking :
Demonstrated ability to align technology initiatives with business strategy.Experience creating multi-quarter roadmaps and executing systematically.Able to evaluate build vs buy decisions and assess new tech vendors or solutions.Project & Team Management :
Strong project management skills able to scope tasks, create realistic timelines, and manage resources for multiple concurrent projects.Experience leading small agile teams, including coordinating with remote / offshore developers if applicable.Ability to mentor and develop junior engineers, instilling best practices in code quality and documentation.Communication & Collaboration :
Excellent communication skills with both technical and non-technical stakeholders.Able to translate complex tech concepts into business implications (and vice versa).Comfortable presenting to C-level executives and training end-users on new systems.Experience in change management guiding users through system / process changes is important in a franchise context.Innovative Mindset :
A problem-solving, curious mentality with desire to innovate in a traditional industry. Track record of proactively identifying inefficiencies and driving creative tech solutions.Education :
Bachelor's degree in Computer Science, Engineering, Information Systems or related field required. Master's degree or relevant certifications are a plus but not mandatory.Our Values. The We Way.
At We Insure Group our values shape how we work, how we lead, and how we growtogether. They're more than just wordsthey guide every interaction, every decision, and every customer experience.
We personalize protection at a price you can trustWe hustle to find opportunityWe care authenticallyWe thrive in ambiguityWe own our resultsWe have fun along the wayAndwe're just getting startedOur Total Rewards
Medical, Dental, Vision, Life, Pet; Flexible Spending AccountCompetitive Salaries401K MatchWork-Life Balance : Personal Days, PTO Days, 12 Paid Holidays, Two Paid Days for Volunteer Service, Paid Parental LeaveShort and Long-Term DisabilityEmployee Support Programs, Including Mental HealthTuition ReimbursementMatching Charitable Gift ProgramLucrative Referral ProgramThis position is not able to be performed in California, Colorado, New York or Washington.
EEO
We Insure Group is an equal opportunity employer that does not discriminate on the basis of race, color, religion, sex (including pregnancy, sexual orientation, and gender identity), national origin, age, disability, veteran status, marital status, or any other protected characteristic. Our hiring practices ensure that all qualified applicants receive fair consideration without regard to these characteristics.
Disability
We Insure Group is committed to creating an inclusive and accessible workplace for all candidates, including those with disabilities. We are dedicated to ensuring equal employment opportunities and providing reasonable accommodations to qualified individuals with disabilities. If you require reasonable accommodations to participate in the application or interview process, please contact our HR department at hrinfo@peak6insurtech.com. We will work with you to provide the necessary accommodations to ensure your full participation in our hiring process.
Note to applicant : It is unlawful in Massachusetts and Maryland to require or administer a lie detector test as a condition of employment or continued employment
