Vice President, Software Engineering & Applications – Senior Health Solutions

The Vice President, Software Engineering and Applications serves as the senior IT leader for Senior Health Solutions, responsible for shaping technology strategy and delivering innovative, customer-centric solutions that support the full lifecycle of Medicare Supplement (Medigap), Senior Dental & Vision, and Hospital Indemnity products. As a key member of the Senior Health Solutions leadership team, this role drives digital transformation, modernizes core platforms, and leverages emerging technologies—including AI and automation—to enhance customer experiences, improve operational efficiency, and support sustainable business growth. Through strong leadership, strategic execution, and a culture of innovation, the VP advances technology capabilities that enable exceptional service for policyholders, providers, distribution partners, and internal stakeholders.

WHAT WE CAN OFFER YOU:

• Estimated Salary: $220,000 - $325,000 based on experience, plus annual bonus opportunity.  
• 401(k) plan with a 2% company contribution and 6% company match.
• Work-life balance with unlimited vacation and paid holidays. See our benefits and perks page for details.
• Applicants for this position must not now, nor at any point in the future, require sponsorship for employment.

WHAT YOU'LL DO:

• Serve as the senior IT leader for Senior Health Solutions, setting the software engineering vision and leading end-to-end delivery strategies that support growth, product innovation, and modernization across Medicare Supplement (Medigap), Senior Dental & Vision, Hospital Indemnity, and related senior health product offerings.
• Oversee the full software engineering lifecycle—planning, development, deployment, and support—ensuring platforms and applications effectively enable underwriting, sales, marketing, product development, policy administration, claims, and servicing capabilities aligned to business priorities.
• Drive modernization of Senior Health Solutions technology platforms, championing Agile, DevSecOps, Continuous Integration and Continuous Delivery (CI/CD), and cloud-native architectures to improve speed to market, scalability, reliability, and digital experiences for policyholders, providers, agents, and distribution partners.
• Build and lead high-performing engineering teams focused on delivering secure, high-quality solutions, fostering a culture of technical excellence, innovation, accountability, and continuous improvement within a highly regulated environment.
• Partner closely with Senior Health Solutions business leaders to translate strategy and requirements into customer- and distribution-centric digital solutions that enable successful and timely execution of strategic priorities.
• Manage and optimize relationships with internal partners, vendors, and third-party solution providers supporting the Senior Health Solutions ecosystem, including enrollment and policy administration platforms, claims systems, customer engagement tools, provider solutions, and digital servicing capabilities.
• Evaluate and responsibly adopt emerging technologies, including artificial intelligence, advanced analytics, and automation capabilities, to improve decision-making, enhance operational effectiveness, elevate customer experience, and create competitive advantages across the Senior Health Solutions business.
  
  

WHAT YOU’LL BRING:

• Minimum 5 years of senior leadership experience across software engineering, application development, IT infrastructure/operations, architecture, or information security, with a proven record of delivering complex, scalable solutions.
• Strong familiarity with compliance frameworks, regulatory expectations, and risk management, with experience in highly regulated environments such as health insurance, annuities, or financial services; plus experience governing multivendor ecosystems, contract negotiation, and performance management.
• Strong expertise in technology planning, solution development, and modern platforms, operating systems, and programming languages, along with knowledge of current and emerging technology trends in health, retirement, accident, annuity, or financial services industries.
• Demonstrated strategic leadership—motivating teams, fostering cross-organizational collaboration and innovation, and building strong business partnerships.
• Exceptional analytical, problem-solving, and decision-making skills with the ability to interpret data, manage risk, and provide sound, innovative recommendations.
• Proven ability to build trusted, collaborative partnerships with senior leaders across IT and the business to align priorities, shape strategy, and drive shared o