Proactive IT leadership Gilmore Solutions positions itself as an outsourced IT partner that focuses on proactive management, long-term strategy, and enterprise-grade security. This suggests opportunities to upsell strategic IT planning, security refresh programs, and IT governance services to mid-market clients seeking reliable, forward-looking support.

Small to mid market focus With 11-50 employees and revenue in the 1M-10M range, Gilmore targets small to mid-sized businesses that require scalable IT leadership and security. Sales efforts can target SMBs in industries relying on robust cloud and security practices, offering bundled packages that scale with growth.

Cloud and security stack Their tech stack includes AWS, Microsoft 365, WordPress, and enterprise-grade security offerings. This signals opportunities to cross-sell cloud migration, migration optimization, security hardening, backup/recovery, and managed AWS/M365 services to clients needing reliable, integrated IT environments.

Recent executive change A new CEO was appointed in 2021, indicating potential organizational priorities around leadership-driven strategy and possible expansion plans. This may present an opening to engage on enterprise-grade outsourcing deals or strategic IT partnerships aligned with new leadership goals.

Customer-first service Emphasis on customer service and understanding client goals suggests a strong value proposition for personalized managed services, SLA-driven support, and customer success programs. This can translate into retainers for ongoing IT oversight, security monitoring, and proactive optimization reviews.