Gifford Tech was built to give every business the IT leadership they deserve. With 26 years of hands-on IT experience — from network technician to Sr. IT Director — Jesse brings real-world expertise and a passion for technology that never stops growing.
Most businesses are stuck in a cycle of reactive IT — fixing problems after they've already cost time and money. Gifford Tech breaks that cycle by building proactive, strategic technology ecosystems that scale with your ambition.
Jesse is genuinely passionate about technology and committed to continuous learning in an industry that never stops changing. He thrives in Microsoft-centric environments and takes pride in keeping systems secure, stable, and aligned with what the business actually needs.
Work With Us →From network technician to Sr. IT Director, Jesse has built, managed, and modernized technology environments at every level — giving you the strategic depth Fortune 500 companies pay hundreds of thousands for.
No bait-and-switch. When you hire Gifford Tech, you get direct access to Jesse on every call, every ticket, every strategy session. No account managers filtering your concerns.
Secured $16K in vendor savings within 6 months. Secured a $250K infrastructure grant. Achieved 99% system uptime. These aren't promises — they're things Jesse has already delivered.
Deep experience with HIPAA-compliant deployments, medical practice systems, telehealth infrastructure, and healthcare data security — critical for any practice or health-adjacent organization.
Scotts Valley-based and proud of it. We serve local businesses with the care and accountability of a neighbor, while bringing national-caliber expertise and vendor relationships.
Same-day response. Clear SLAs. Transparent reporting. And we never get kickbacks for recommending specific vendors — every recommendation is purely based on what's right for your business.
Led complete overhaul of a previously underperforming IT infrastructure, achieving 99% system uptime. Untangled and rebuilt a severely misconfigured ETQ Quality Management System. Secured $16K in vendor savings within the first 6 months. Following acquisition, served as onsite IT lead for a Microsoft 365 tenant-to-tenant migration with zero data loss, and directed Cisco Meraki network consolidation into the parent organization.
Led transition from fully outsourced IT to a built-from-scratch in-house team. Secured a $250,000 infrastructure grant to deploy state-of-the-art hardware including Cisco Meraki switches. Deployed HIPAA-compliant telecommuting and telehealth tools during COVID-19. Administered firewall/VPN, VMware, and Active Directory across multiple sites; developed and maintained a multi-year IT roadmap aligned to organizational goals.
Researched and integrated new technologies including Backup Exec 15. Upgraded Exchange 2013 and restructured Active Directory, improving functionality and strengthening security. Conducted daily system assessments across networks, servers, and workstations to identify and resolve issues proactively.
Designed and deployed network infrastructure including Site-to-Site VPN, workstations, servers, and Exchange 2013 across 4 external client offices. Advised medical practices on selecting HIPAA-compliant systems. Deployed Sophos Disk Encryption across all systems.
Developed and deployed software solutions using VB.Net. Managed IT infrastructure projects including network design for new office build-outs and Avaya phone system deployment. Resolved complex technical issues via remote and on-site support.
Led major IT modernization — Novell to Windows Active Directory migration and overhaul of 200 PC workstations. Designed and deployed LAN infrastructure to support SAP rollout. Built a custom real-time IT monitoring solution with web-based dashboard. Earned the prestigious McCormick Gold Award for exemplary performance.
26 years of hands-on technical depth across enterprise IT environments, with a business-first mindset that translates technology into measurable outcomes.
Whether you need a full MSP partner or a fractional IT Director, we're ready to help.
