Kirk Gleason

Bloomington, IN | kirk@kirkg.us | linkedin.com/in/kgleason

Professional Summary

IT and security leader with a track record of building things that didn’t exist before and making existing things work better. I’ve stood up enterprise security programs from scratch, led infrastructure modernizations that cut seven figures from annual budgets, and maintained a perfect SOC 2 audit record for over seven consecutive years. My teams have shipped SaaS products, migrated legacy systems to modern architectures, and kept 500+ person organizations running securely. I solve problems, I teach people how to keep solving them after I leave, and I do both without making it more complicated than it needs to be.

Technical Skills

Security & Compliance: HITRUST, SOC 2 Type 2, HIPAA, Third-Party Risk Management, Security Audits, Vulnerability Assessments, Encryption (OpenPGP/PGP), Endpoint Security, Firewall Management

Infrastructure & Networking: VPN (WireGuard, IPSec, OpenVPN), Network Architecture, DNS, VoIP/Telephony Systems, Server Administration, Private Cloud Infrastructure

Development & DevOps: CI/CD (Jenkins, Octopus Deploy), SaaS Architecture, Mobile App Development (iPad/iOS), Web Application Development, Database Design (PostgreSQL, SQL Server, MySQL, Sqlite)

Cloud & Platforms: AWS, SaaS Deployment, Email Systems (Zimbra, Exchange, Google Workspace, Postfix), System Integration, API Development

Professional Experience

Bloom Insurance Agency, Bloomington IN | 2012 - 2026

Hired as Director of IT to build and lead the technology organization. Promoted to VP after establishing the company’s first formal information security program and expanding my role to own the enterprise technology and security strategy alongside C-suite leadership.

VP Information Systems & Security | 2017 - 2026

  • Directed annual SOC 2 Type 2 compliance initiatives, achieving a 100% audit success rate over 7+ consecutive years
  • Designed and implemented the company’s Third-Party Risk Management program from the ground up, evaluating 50+ vendors and reducing security exposure by 40%
  • Cut $1.25M (18%) from the annual technology budget — from $7M to $5.75M — while improving operational capabilities
  • Led infrastructure modernization by migrating from Windows EC2 instances to containerized Linux architecture, reducing AWS compute costs by 30% during peak enrollment
  • Modernized VPN infrastructure by replacing IPSec with a WireGuard-based architecture, improving connection speeds by 60% and VPN stability by 80%
  • Owned IT operations, network infrastructure, and support services for a 500+ person organization, driving measurable improvements in system reliability and team performance across annual planning cycles
  • Worked with C-suite to align technology roadmap and security strategies with business objectives, contributing to 30% year-over-year revenue growth
  • Built and led the vulnerability management program; identified and prioritized remediation efforts that reduced critical vulnerabilities by 85% within the first year

Director, Information Technology | 2012 - 2017

  • Defined the IT strategy from scratch — technology priorities, governance standards, and multi-year roadmaps aligned with organizational goals
  • Built and managed cross-functional teams of network engineers, system administrators, and software developers (15+ direct and indirect reports)
  • Led end-to-end design and deployment of multiple SaaS products, including data modeling, mobile app architecture, CI/CD pipeline development, and private cloud infrastructure
  • Launched an iPad application for Medicare Advantage sales that processed 5,000+ applications annually; architected the full-stack solution and managed deployment
  • Built a web application for multichannel Medicare Advantage processing that cut processing time by 50% and improved data accuracy
  • Automated 20+ manual processes and integrated third-party systems, saving 1,000+ labor hours annually
  • Converted manual build processes to automated CI/CD using Jenkins and Octopus Deploy, reducing deployment time by 65% and improving build reproducibility by 95%
  • Managed IT operations, $2M+ annual budget, software lifecycle planning, and strategic vendor partnerships

Finelight, Bloomington, IN | 2003 - 2012

Started as a systems engineer supporting call center infrastructure. Promoted to IT Director within three years after leading the VoIP migration and proving I could keep a 300+ seat operation running while simultaneously improving it.

IT Director | 2006 - 2012

  • Maintained mission-critical server, network, and telephony infrastructure supporting 300+ seat call center operations
  • Implemented enterprise VoIP network, reducing telecom costs by 35% while improving call quality and reliability
  • Led large-scale infrastructure relocation with zero downtime; coordinated network design and deployment for branch offices in Louisville, Chicago, Jacksonville, and New York

Systems Engineer | 2003 - 2006

  • Implemented OpenVPN and IPSec VPN solutions, establishing remote connectivity across the organization
  • Administered PostgreSQL and SQL Server databases for call center operations; maintained 99% uptime and optimized query performance

Education

Indiana University | Masters, French Literature

Hartwick College Bachelors, French