Join to apply for the Director of Software Development role at Great Gray Trust Company Join to apply for the Director of Software Development role at Great Gray Trust Company RPAG is a wholly owned subsidiary of Great Gray Group, LLC. Acquired in 2024, RPAG hosts the industry’s leading retirement plan practice management platform. Designed for elite advisors and institutions, our goal is to create successful outcomes by protecting plan fiduciaries and engaging plan participants. Our efficient and scalable technology platform provides our members with actionable insights, allowing them to make data-driven decisions for their retirement plan clients. At Great Gray Group, we strive to set the bar for the retirement services industry. Our goal is to deliver advanced retirement solutions that combine our core fiduciary services with robust investment options, innovative technology, and dedicated client service. We focus on making choices clearer, transitions smoother, and the client experience more delightful. Complacency isn't in our vocabulary. Every day, we look for opportunities to better serve our clients, be an excellent business partner, and earn the trust of those who rely on us. The Role Great Gray is looking to add a Director of Software Development to lead and grow RPAG’s engineering teams, reporting directly to the Chief Technology Officer. This is a unique opportunity for a hands-on leader to manage and mentor high-performing teams while shaping our technology landscape. The role requires a deep understanding of software architecture, particularly in data-driven applications, and an ability to transition our current offshore development model to a hybrid in-house structure over time. Location This position will work from our Boston, MA office. Great Gray currently supports a hybrid work model with 4 days onsite, and 1 day remote. Visa sponsorship or transfer of an existing visa is not available for this position. Applicants must be authorized to work directly for any employer in the United States without visa sponsorship or transfer. Responsibilities Manage and scale two Scrum teams, ensuring high performance and collaboration as our organization expands. Drive technical strategy, architecture, and execution for our data-intensive applications. Develop a transition plan to build in-house engineering capabilities while effectively managing offshore teams. Partner with Product, Design, and Data teams to align technology solutions with business goals. Foster a high-performing engineering culture focused on ownership, innovation, and continuous learning. Oversee the quality, scalability, security, and performance of our applications and integrations. Mentor and develop engineering talent, providing career growth opportunities and constructive feedback. Stay informed about emerging technologies (e.g., AI) and industry best practices to drive innovation. Ensure alignment with client and dependency teams on expectations, processes, and deliverables. Contribute to the broader engineering organization’s initiatives, including hiring, hybrid work policies, and company-wide programs. Complete other related duties as assigned Qualifications & Experience Proven experience leading and scaling engineering teams, ideally in a startup or fast-paced environment. Strong understanding of software architecture and best practices for building data-intensive applications. Experience managing offshore teams and transitioning to an in-house model. Hands-on technical expertise with a willingness to dive into complex engineering challenges when necessary. Strong leadership and coaching abilities to develop and retain top engineering talent. Ability to balance technical excellence with business objectives, ensuring technology decisions drive company growth. Experience collaborating with cross-functional teams to deliver customer-centric solutions. Excellent communication skills and ability to translate technical concepts into business impact. Ability to thrive in a fast-paced, dynamic environment and manage multiple priorities effectively. Comfortable navigating ambiguity. Entrepreneurial mindset to bring best practice ideas to the team. Your standards reflect our core values: Growth Mindset, Disciplined Curiosity, Grit, Results-Driven, Collaborative. We have a comprehensive and competitive benefits package at Great Gray. Some of the highlights are: Be an integral part of an early-stage, high-growth organization! Hybrid work environment Competitive compensation package including 401(k) with elective and non-elective match opportunities Lifestyle spending allowance program Employer-paid life and disability insurance Generous paid time off program Investor Background MDP is a leading private equity investment firm based in Chicago. Since MDP's formation in 1992, the firm has raised aggregate capital of over $28 billion and has completed over 150 platform investments. MDP invests across five dedicated industry verticals, including basic industries; business and government software and services; financial and transaction services; health care; and telecom, media, and technology services. Equal Employment Opportunity Policy Great Gray, LLC is an Equal Opportunity Employer. Qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender perception or identity, national origin, age, marital status, protected veteran status, disability status or other non-merit factor. Seniority level Seniority level Director Employment type Employment type Full-time Job function Job function Engineering and Management Industries Financial Services and Software Development Referrals increase your chances of interviewing at Great Gray Trust Company by 2x Inferred from the description for this job Medical insurance Vision insurance 401(k) Disability insurance Paid paternity leave Paid maternity leave Get notified when a new job is posted. Sign in to set job alerts for “Director of Software Engineering” roles. 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