Michael Gary

About Michael Gary

As a strategic operations leader with 15+ years of experience across SaaS, consulting, and education technology, I’ve built a career at the intersection of mission, metrics, and modernization. Whether scaling a multi-state service org or reducing churn by over 50%, I specialize in translating cross-functional strategy into measurable impact.At Concentric Educational Solutions, I’ve led transformative growth: launching enablement playbooks that boosted ARR by $2.35M, aligning KPIs across sales, customer success, and product, and deploying dashboards that empower teams to act on insights, not just data.My leadership spans COO-level operations—overseeing a $7.5M P&L, 150+ staff, enterprise vendor strategy, and digital systems rollout. I’ve implemented compliance apps, automated reporting flows, and improved EBITDA margins through cost optimization and accountability frameworks.What drives me? Helping organizations deliver excellence through operational clarity, team alignment, and tech-enabled service. I lead with empathy, challenge with data, and build culture through collaboration. Keywords: Strategic Planning | PowerBI | Cross-Functional Leadership | KPI Development | MSP/Tech-Enabled Ops | Change Management | P&L Ownership | Process Automation | ConnectWise (or CRM)| Customer Retention | Talent Enablement | SaaS Delivery | COO ReadinessIf you\'re solving for scale, efficiency, or modernization, I’d love to connect.

Experience

1. Chief of Staff and Customer Engagement

   Concentric Educational Solutions

   Jun 2018 — Present

   Designed and launched a cross-functional enablement roadmap across 12 states, integrating AI-powered support workflows and lifecycle communication tools.• Manage a diverse team of 12 (product, analytics, marketing, project ops) and a distributed group of regional Senior Directors.• Improved customer retention by 55% and reduced churn from 9% to 4%, while accelerating expansion velocity by 18%.• Scaled onboarding and renewal playbooks in collaboration with Sales, CS, and Product—generating $2.35M in ARR from 30 net-new and 23 renewed accounts.• Led a distributed team of Senior Directors (RVP-equivalent), aligning performance goals, KPIs, and enablement across high-impact regions.• Acted as a strategic advisor to executive leadership on operations, communications, and client-facing initiatives; facilitated alignment across GTM teams and funding strategies (ESSER, Title I, IDEA).• Developed dashboards to monitor success metrics, shorten time-to-value, and improve client lifecycle performance.• Spearheaded professional development and training efforts, resulting in improved employee engagement and higher NPS scores.Keywords: Customer Retention | GTM Enablement | ARR Growth | Cross-Functional Strategy | Lifecycle Engagement | AI-Powered Support | Strategic Operations | Churn Reduction

Education

• Lincoln University

  Bachelor's degree

  1999 — 2005

• Mercer University

  Doctor of Philosophy (Ph.D.)

  2013 — 2016

• General Assembly

  User Experience Design Certification

  2019

• University of Massachusetts, Amherst

  Master's de

  2007 — 2009