Sr. Director of Technology & Product

Keystone Advisors Overview

At Keystone Advisors we partner with top insurers to help clients find essential health coverage in 49 states. We provide individuals, families, and businesses with health, dental, vision options, as well as Medicare options including Medicare Advantage, Medicare Supplement Insurance, and Prescription Drug Part D plans.

We are experts in the health insurance market and define our outstanding performance. Our team gives their best to match our clients' needs. We are proud of helping thousands of Americans to find peace of mind and economic stability. Even though many things have changed throughout the decades, one thing remains the same: We are the key to finding the right health plan for you.

Job Purpose

We are seeking a forward-thinking and execution-driven Sr. Director of Technology & Product to lead the development and innovation of Keystone's technology platforms. This senior leader will own the technology roadmap, drive the evolution of internal tools and SaaS offerings, and oversee the engineering and product teams. The ideal candidate will blend strong technical expertise with strategic product vision to improve operational efficiency, platform performance, and user experience.

Duties and Responsibilities

• Leadership of Engineering and Product Teams Lead cross-functional teams of developers, product managers, and QA specialists in delivering high-quality software solutions. Foster a culture of agility, innovation, and technical excellence.

• Technology Roadmap & Product Strategy Define and maintain a clear, scalable technology roadmap that aligns with company goals and future growth. Drive product development cycles from ideation through launch and iteration.

• Cross-Department Collaboration Work closely with sales, broker support, sommission, contracting, and customer service teams to identify automation opportunities and build tools that improve workflows and outcomes. Translate business needs into technical requirements and scalable solutions.

• Platform Management & Performance Optimization Oversee the performance, reliability, and uptime of internal and external SaaS platforms. Implement strong QA processes, monitoring, and documentation practices to ensure platform excellence.

• Vendor & Integration Oversight Manage third-party technology partnerships and software integrations. Evaluate vendors and ensure all technology solutions align with compliance and scalability needs.

Qualifications

Required Qualifications • Bachelor's degree in Computer Science, Engineering, or related field • 8+ years of experience in software development, product management, or technology leadership • Strong experience with SaaS platforms, enterprise applications, and cloud infrastructure • Proven ability to lead technical teams and drive complex projects to completion • Proficiency in modern development tools, CI/CD, and software lifecycle best practices • Strong communication skills with the ability to collaborate across technical and non-technical teams

Preferred Qualifications • MBA or master's in technology management or related field • Experience in the insurance, healthcare, or financial services industries • Familiarity with Salesforce, HubSpot, AWS, and third-party integrations • Background in UX/UI best practices and data-driven product management

Working Conditions

• Business office environment • Flexibility for hybrid or remote work arrangements • Occasional extended hours or weekend work during major product deployments or updates