I'm Stephen Hare, a technology executive with 29 years in IT and more than 15 in senior leadership. I rebuild fragile, aging environments into stable, secure, modern platforms, and I lead the teams and budgets that keep them that way. I came up hands-on, and I never left the engine room.
I walk into environments that are fragile and walk out with ones that simply work.
My current environment was failing when I arrived: internet down for days at a time, broken directory services, identity scattered across disconnected systems. Within months I rebuilt the network, fixed the core, raised the directory to current standards, and unified everything behind single sign-on and multifactor. It has not had unplanned downtime in over a year. That is the pattern of my career. I stabilize what is broken, modernize what is dated, and harden what is exposed, then I lead the team and the budget that keep it healthy.
I fix the foundation before chasing the new thing. Reliability comes first, because nothing else matters if the systems are down.
I came up as a DBA and engineer, and I still work at that level. I lead from inside the problem, which is why my teams trust the plan and my stakeholders trust the result.
Nearly 30 years in, I am building private LLMs and full-stack tools for the organizations I serve. Deep experience and modern practice are not a tradeoff.
Senior infrastructure leadership is full-stack by definition. I am accountable for every layer below, from the hardware in the rack to the budget in the boardroom. Select a layer to see how I work in it.
Servers, virtualization, and the physical plant beneath everything. I have rebuilt entire environments from scratch, including a server room I fully virtualized, retiring more than 40 physical servers and cutting related energy use by over 80 percent. I run VMware and Hyper-V clusters, SAN storage, and the core services everything else depends on.
Nearly three decades of hands-on technology leadership across public and private sectors, from database administration to running IT for a city and its schools.
Senior IT leader for the city and its school district, accountable for infrastructure, security, vendors, and technology direction across municipal and school departments. I walked into a failing, aging environment and rebuilt it end to end: I resolved the Active Directory and DNS failures that broke logins between buildings, moved everyone onto Microsoft 365 and Entra ID, and virtualized the server room, retiring more than 40 physical servers and cutting related energy use by over 80 percent. I hardened it with Duo MFA, Huntress MDR/XDR, Defender for Endpoint, security-awareness training, and a three-tier backup that ends in ransomware-proof WORM cloud storage. The result is a once-broken environment with no unplanned downtime in over a year. I manage a $1.3M budget, lead a 5-person team, fund projects through state grants, and present plans to the mayor, school board, and city council.
Ran IT infrastructure and operations for a hybrid Active Directory and Azure environment across multiple offices in the insurance and risk sector, where the business grew from 66 to over 110 employees on my watch. I migrated roughly 90 users from on-site Exchange to Microsoft 365 in three weeks with no interruption to their work, moved the phone system across RingCentral, Zoom, and Ooma, and held production systems to under a day of downtime per year. I led the company's annual SOC 2 audits and coordinated PCI compliance with the CFO, wrote and enforced HIPAA and Massachusetts 201 CMR 17 privacy policies, tuned the SQL Server backend of the core insurance platform, and presented annual budgets to the C-suite and partners.
Led 24/7 technical operations for a commercial cloud backup platform serving around 400 business customers and 200 to 300 TB of data. I managed a large VMware and SQL Server environment of 42+ servers against a 15-minute SLA, built an AWS-hosted virtual environment, and automated operations with PowerShell. The platform had daily database failures when I arrived; I rebuilt the SQL environment and maintenance plans, resolved 99 percent of the recurring issues, and held full SLA compliance for the six months before I left.
Kept a 24/7 production SQL Server environment running for a high-volume email delivery business, with VMware clusters, SAN storage for high-IOPS workloads, and PostgreSQL and Linux systems supporting the core service.
Managed a 100+ server SaaS testing environment that ran daily call-testing for major clients including Apple and Zipcar, with each server handling 50 to 60 simultaneous calls. I kept the platform reliable and scaled it as the business grew, across SQL Server, Active Directory, Exchange, VMware, and network infrastructure.
Earlier roles built the foundation: early-career healthcare IT doing server and network maintenance for hospitals at Multimedia Medical Systems and systems engineering at Winchester Hospital, then four years running my own IT firm for small businesses before All Covered acquired it and kept me on to serve those clients. The database, network, and infrastructure depth from those years is what lets me lead from inside the work today.
I started as a database administrator and a network engineer, owned my own technology business, and worked through hosted infrastructure, cloud backup, and SaaS operations before stepping into senior leadership. That path means I have done almost every job I now lead, which is exactly why I can lead it well.
I am a Microsoft Certified DBA with a Master's in Information Systems Management from Brandeis, and I am still learning: building private LLMs for the organizations I serve, writing full-stack tools, and earning new certifications. I also write regularly for other IT leaders, usually on the unglamorous truths of running technology, like why the hardest problems are rarely technical and why clear communication beats another tool every time.
Outside of work, I am a published novelist, author of the Chasing Light science fiction series. Storytelling and systems engineering use more of the same muscles than people expect: structure, patience, and a clear picture of where it all has to end up.
I am based in the Greater Boston area, open to remote leadership roles, and relocating to Florida.
100+ server environments, VMware and Hyper-V clusters, SAN storage, and the core services that hold everything together.
Azure and Entra ID, Microsoft 365, Google Workspace, and AWS, with hybrid environments and single sign-on across the org.
Microsoft Certified DBA. SQL Server administration, performance tuning, data warehousing, and analytics at scale.
Multi-site LAN and WAN, Cisco and HP switching, Fortinet and Meraki firewalls, large VoIP deployments, and device management with Intune, Jamf Pro, and Apple Education Manager.
MFA, MDR and XDR, endpoint protection, SOC 2 and PCI audit leadership, HIPAA and state privacy compliance, and ransomware-proof backup and disaster recovery.
Private, privacy-safe LLMs for staff and students, AI-assisted and full-stack development, and PowerShell automation that removes manual work.