At Heywood Enterprises, we specialize in empowering individuals, families, and organizations through technology and financial guidance. With decades of experience in IT leadership and financial counseling, we provide practical solutions that help you thrive in today’s fast-paced world.
Whether you’re navigating complex financial decisions, seeking clarity in budgeting, or leveraging technology to streamline your operations, we’re here to guide you with expertise and compassion. Our mission is simple: to equip you with the tools, knowledge, and confidence to build a secure future.
From IT consulting and systems management to personal and organizational financial planning, Heywood Enterprises blends technical excellence with real-world insight. We believe that strong finances and smart technology are the foundation for lasting growth, both personally and professionally.
Let’s work together to unlock your potential, strengthen your financial health, and harness the power of technology to achieve your goals.

Robert Heywood - Strategic Thinker in Technology, Finance, and Operations
Robert brings a unique blend of IT leadership and financial expertise, with more than 25 years in executive technology management and over 30 years of experience in non-profit and personal finance management.
This rare combination allows him to not only design and oversee complex IT infrastructures but also guide individuals, families, and organizations toward financial stability and growth.
In the financial realm, Robert has helped non-profits strengthen their fiscal health through budgeting, resource allocation, and long-term planning, while also assisting individuals with personal finance management—providing practical strategies for debt reduction, savings, and financial confidence.
Professionally, Robert served in Executive roles at Harvard University’s School of Engineering and Applied Sciences, where he managed IT support services, deployment, infrastructure platforms, and 24x7 operations for faculty, staff, and students. His expertise spans datacenter management, virtualization, enterprise storage, and cross-organizational project leadership.
His career includes IT leadership roles at Harvard Vanguard Medical Associates and INSO Corporation/eBusiness Technologies, where he directed global IT operations and managed large-scale technical teams. He has also provided consulting services to schools, businesses, and churches, combining technical insight with financial stewardship to deliver holistic solutions.
Robert’s dual focus on technology strategy and financial management positions him as a trusted advisor who helps organizations and individuals thrive by aligning resilient IT systems with sound financial practices
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