My Resumé
Kirk Gleason's - Resume
Professional Summary
Strategic IT and Security professional with over 20 years of experience driving enterprise technology transformation and risk management. Proven ability to design and implement secure, scalable infrastructures that align with business objectives and regulatory requirements. Expertise spans cybersecurity frameworks, network architecture, and cloud solutions, complemented by a strong background in database design and telephony systems. Recognized for delivering innovative solutions, optimizing operations, and leading high-performing teams in dynamic, growth-oriented environments.
Core Competencies
- Enterprise IT Strategy & Governance
- Cybersecurity & Risk Management
- Network Architecture & Infrastructure
- Cloud Solutions & SaaS Deployment
- Regulatory Compliance (SOC 2, HIPAA, CCPA)
- CI/CD & DevOps Practices
- Vendor & Third-Party Risk Management
- Team Leadership & Budget Oversight
Professional Experience
Bloom Insurance Agency - Bloomington, IN
VP, Information Systems & Security | July 2017 - Present
- Lead enterprise information security strategy, including risk management, regulatory compliance, and security operations.
- Conduct security audits and risk assessments; design and implement mitigation strategies.
- Modernized VPN infrastructure, transitioning from IPSec to WireGuard-based architecture.
- Manage firewall configurations and endpoint security across network and operating systems.
- Oversee encryption tools (OpenPGP/PGP) to safeguard sensitive data.
- Developed and implemented Third-Party Risk Management program.
- Directed annual SOC 2 Type 2 compliance initiatives.
- Collaborate with executive leadership to align technology and security strategies with business objectives.
- Drive improvements in IT operations, network infrastructure, and support services through strategic planning and oversight.
Director of Information Technology | August 2007 - July 2017
- Defined IT strategy aligned with organizational goals; established technology priorities and governance standards.
- Managed teams of network engineers, system administrators, and software developers across infrastructure and application domains.
- Led design and deployment of SaaS products, including data modeling, mobile app architecture, CI/CD pipelines, and private cloud infrastructure.
- Oversaw development of new product lines:
- 2011: iPad application for Medicare Advantage sales, including full-stack architecture and deployment.
- 2013: Web application for processing Medicare Advantage applications via multiple channels.
- Implemented automation for manual processes and integrated numerous third-party systems.
- Migrated email services from CommunigatePro to Zimbra; managed telephony servers and DNS configurations.
- Converted manual build processes to CI/CD using Jenkins and Octopus Deploy.
- Directed IT operations, budgeting, software lifecycle planning, and vendor integrations.
- Managed staff of engineers, developers, and project managers; fostered a culture of accountability and innovation.
Finelight - Bloomington, IN
IT Manager | June 2006 - December 2009
- Oversaw day to day IT operations, including infrastructure management and support services.
- Managed 2 different email platform migrations
- Coordinated IT projects, vendor relationships, and technology upgrades
- Lead technology component of multiple office relocations, openings, and closures
Systems Engineer | March 2003 - June 2006
- Maintained server, network, and telephony infrastructure; administered PostgreSQL databases for call center operations.
- Developed applications for call center operations, including VB6 and Java solutions for call handling and secure audio retrieval.
- Migrated legacy systems to modern architectures, including PostgreSQL to SQL Server and VoIP network implementation.
- Coordinated large-scale infrastructure moves with minimal downtime; designed and deployed networks for branch offices in Chicago, Jacksonville, and New York.
Education
Indiana University | Masters of French Literature | 1998 - 2003
Hartwick College | Bachelors of French | 1992 - 1996