Gary Dobkin

Built EUCompli.ai from concept into a working Rails 8 and PostgreSQL platform for GDPR and EU AI Act compliance, with authentication, authorization, Solid Queue, audit logs, and MCP-based AI integration. Designed governed AI workflows with structured outputs, durable task state, human approval gates, and audit-ready evidence required before any external action. Built operator-facing workflows across support, sales, CRM, and service operations so AI execution stayed tied to real business outcomes, reducing implementation burden and time-to-value.

Advise startup founders and operators on practical, fit-for-purpose AI adoption: assess where automation pays off, build the roadmap, and deliver or guide the build across finance, CRM, sales, support, and customer success. Ship internal tooling, AI-enabled workflows, and agent architectures with the controls, documentation, and handoff teams need to run them without me. Apply honest judgment on where AI helps versus where a simpler fix wins, pairing each build with the change management that turns it into durable capability the business owns.

Built ConnectWise's complete security-stack onboarding program from the ground up: operating model, team structure, and 30-day implementation cycles for IDS, SIEM, EDR, and MDR across US, EMEA, and APAC. Directed 18 Security Consulting Experts within a 26-person global organization across 18+ security and SaaS offerings, including SentinelOne and Bitdefender EDR/MDR, StratoZen and Perch SIEM, Webroot, Data Protection Suite, and Vulnerability Management. Drove CSAT above the 88% target three years running (93.7% in 2022, 94.93% in 2023, 96.7% in 2024) with 24-hour SLA/SLO compliance, and launched 18 new security products. Reported to C-level and GM leadership in weekly and quarterly business reviews, and led a billing audit that recovered $1.575M in unrealized annual contract value.