Senior Software Engineer

About Ironwood Digital Advisors We're building healthcare tech for a system that desperately needs it. Each year, millions of Americans deal with confusing changes to their Medicare plans that impact their prescriptions, access to care, and pocketbooks. These aren’t just inconveniences – they are potentially life-altering changes that leave seniors medically and financially vulnerable. Independent Medicare advisors play a crucial role in guiding seniors through this complexity and helping them find the right coverage for their needs. But their ability to be effective healthcare advocates has long been hamstrung by broken tools and outdated systems. Ironwood Digital is fixing that. We’re the fastest-growing Medicare platform in the country, combining AI, an industry-leading CRM, and client services to transform how 10,000+ brokers acquire, enroll, and support clients in their local communities. Join a talent-dense team from Square, Ramp, Yext, Oscar, and Cedar — backed by Primary Ventures and Viewpoint Ventures — that is serious about building technology to expand access to quality healthcare. We offer remote work, sabbaticals, company retreats, and other generous benefits that earned us recognition as one of Inc. Magazine’s Best Workplaces of 2025 Healthcare is overdue for innovation. Let’s redefine what its future looks like — together. Ironwood Digital is looking to bring on a Senior Software Engineer that will drive progress in the Medicare industry's evolution. As a senior member of our engineering team, you'll work to ensure our technical platform continues to meet the needs of our rapidly growing customer base. This will involve delivering impactful feature sets to our industry-leading web-based broker platform while making architectural decisions to support its long-term health and stability. Your day-to-day responsibilities will be diverse: you'll engage in both frontend and backend development, collaborate with product and design teams on new features, and work with other engineers to scale our solutions. What you'll do Deliver impactful full-stack features that will benefit Medicare brokers and beneficiaries Work closely with product to understand the relationship between agents and Medicare beneficiaries, developing features that improve retiree outcomes Collaborate with cross-functional teams to provide constructive feedback on design mockups and product scope Identify and manage technical debt while building robust architectures to support platform scalability Actively contribute to development standards by promoting best practices and giving constructive feedback in code reviews and technical designs Build with modern AI-powered developer tools that remove friction and let you focus on meaningful problems - and help us continue to grow how we use them across the team. What we're looking for 5+ years of professional experience with either modern JS (Vue, React) or Python/backend web development, with meaningful hands-on experience in both Comfort with ambiguity; ability to thrive in fast-paced environments Product intuition and a keen interest in how tech investments drive business outcomes Fluency with AI-powered development tools as part of your everyday workflow Strong communication and project management skills Attention to detail and a history of technical excellence shipping customer-facing products Commitment to a growth-oriented team culture focused on learning, continuous improvement, and winning together Nice to haves Experience working directly with cloud infrastructure (AWS preferred) Expertise in Django or similar Track record in technical or project leadership Our salary ranges are based on paying competitively for our company’s size and industry, and are one part of the total compensation package that also includes equity, benefits, and other opportunities at Ironwood Digital. In accordance with New York City, Colorado, California, and other applicable laws, Ironwood Digital is required to provide a reasonable estimate of the compensation range for this role. Individual pay decisions are ultimately based on a number of factors, including qualifications for the role, experience level, skillset, geography, and balancing internal equity. A reasonable estimate of the current salary range is listed below . We expect most candidates to fall in the middle of the range. We also believe that your personal needs and preferences should be taken into consideration, so we allow some choice between equity and cash. Base Salary $165,000 — $190,000 USD Why you should join our team By joining Ironwood Digital, you will get in on the ground floor of a fast-moving, well-funded, and mission-driven startup where you will have a profound impact on the brokers and beneficiaries we serve. And you'll learn, grow, be challenged, and have fun with your team while doing it. We strive to help you and your family thrive. We're committed to supporting your happiness, healthiness, and overall well-being by providing a comprehensive benefits program. In addition to your base s