Michael Reagan

Customer Support Operations & Customer Experience Leader

Michael Reagan

Director-level leadership designing scalable support and customer experience systems through process, data, and AI.

Focused on improving efficiency, customer experience, and operational performance at scale.

Professional headshot of Michael Reagan

Transforming Support Operations Through Leadership, Innovation, and AI

I’m a senior operations and customer support leader who helps organizations scale support, improve customer experiences, and drive operational excellence. By combining strong leadership, data-driven decision-making, and AI-powered innovation, I build teams and systems that deliver measurable results.

About

With 24 years of experience leading customer support and operations teams — including more than 12 years in Director-level leadership — I’ve built my career around solving complex challenges and creating scalable solutions. My expertise spans support operations, incident management, process optimization, and AI-driven transformation, with a focus on improving both customer outcomes and business performance.

Throughout my career, I’ve partnered closely with Product, Engineering, and business leaders to modernize support organizations, implement automation, and develop high-performing teams. I believe great operations are built at the intersection of people, process, and technology, and I’m passionate about creating environments where teams can do their best work while delivering exceptional customer experiences.

When I’m not driving operational improvements, I’m exploring emerging AI technologies, mentoring leaders, and finding new ways to transform how teams work and scale.

Approach

The way I approach support operations combines operational discipline, data fluency, and practical AI adoption.

Operational system design

Building repeatable support models, playbooks, and operating rhythms that scale with complexity.

Process optimization at scale

Identifying friction, reducing waste, and redesigning workflows to improve speed and consistency.

Data-driven decision making

Using metrics, dashboards, and performance signals to prioritize the highest-impact improvements.

AI-assisted support workflows

Applying AI to improve triage, reduce administrative effort, and accelerate support resolution.

Experience

Senior Director, Customer Support

Aug 2021 – Mar 2026

Anywhere Real Estate (formerly ZipRealty → Zaplabs → Realogy; became Compass International Holdings in 2026) · Emeryville, CA

Led a Tier 2 customer support organization of approximately 30 employees, including 3 direct-report leaders, supporting approximately 40,000 tickets annually in a mission-critical production environment.

  • Reduced Mean Time to Resolution (MTTR) for Incidents from 2 days, 23 hours to 20 hours (≈71% reduction), and for Service Requests from 4 days to 2 days, 9 hours
  • Drove AI-enabled operational transformation through the rollout of ServiceNow NowAssist, leading an enterprise change management initiative to embed AI into daily workflows
  • Turned around an underperforming ServiceNow development team by introducing a scrum master and instituting Agile methodology — significantly improving throughput and enabling the team to deliver more with fewer resources
  • Improved CSAT while simultaneously increasing ticket volume and operational complexity, and delivered measurable gains in First Contact Resolution (FCR) and agent efficiency
  • Owned end-to-end performance for escalations, incident management, service requests, and problem management, including department operating budget, vendor contracts, headcount, training, and tooling spend
  • Designed and owned support analytics and dashboards using ServiceNow and BI tools
  • Partnered closely with Product, Engineering, and SRE teams to drive root-cause analysis and inform roadmap priorities
  • Built scalable processes, playbooks, and knowledge management systems to standardize execution across a distributed team
  • Coached and developed 3 senior managers and ~30 team members through structured performance management, career pathing, and succession planning
  • Acted as the senior escalation point for high-impact customer and executive issues, maintaining trust and transparency during critical incidents

Director, Customer Support

Aug 2019 – Aug 2021

Anywhere Real Estate · Emeryville, CA

Led the teams responsible for Tier 3 support, Quality Assurance, and Zap platform development — continuing the tiered model established as Sr. Manager — with accountability for KPIs, SLAs, quality, and cross-functional collaboration with engineering and product teams.

  • Led a Tier 3 support team of 4 FTEs, owning KPIs including CSAT, SLA attainment, and quality performance standards, and reducing L3 escalations through targeted training, workflow redesign, and improved cross-team collaboration
  • Directly managed the QA organization (1 manager, 2 FTEs, and 3 contractors) responsible for manual and automated testing of Zap, serving as the bridge between Support and Product to prioritize and validate bug fixes
  • Took ownership of the Zap development team (outsourced: 2 onshore, 4–10 offshore) following major organizational restructuring, leading it through maintenance mode to the successful sunset of Zap, a legacy proprietary CRM that let real estate agents track client activity on a connected customer-facing site and market to them accordingly — including full data migration to a new third-party system, MoxiWorks

Sr. Manager, Customer Success (Support Operations)

Mar 2016 – Aug 2019

Anywhere Real Estate · Emeryville, CA

Designed and led an 11-person, three-tier (T1/T2/T3) support organization built from the ground up — including creating and leading the new Tier 3 team — while administering and optimizing Zendesk to improve case routing, reporting accuracy, and executive-level visibility into customer issues.

  • Created a new Tier 1/Tier 2/Tier 3 structure (11 FTEs total) to align support resources by skill level — significantly improving resolution time
  • Established a rigorous governance process for Tier 3's elevated system access, including direct database query/write privileges, requiring sign-off from three directors and DBA testing before production deployment
  • Administered and optimized Zendesk (CRM) for Success and Support teams, improving routing and reporting accuracy

Customer Support Manager

Nov 2013 – Mar 2016

Anywhere Real Estate · Emeryville, CA

Built and led an 8-person frontline support team, implementing standardized workflows, Zendesk automation, and knowledge base content to improve operational efficiency and customer self-service.

  • Implemented scalable support model and authored knowledge base content to improve self-service
  • Built routing rules and workflows in Zendesk to streamline case handling
  • Also led Client Services, a consumer-facing support team for the company's public real estate search website, ensuring compliance with ADA accessibility standards, NAR and MLS data-display requirements, and state real estate regulations — including managing periodic penetration testing and responding to escalated BBB complaints

Early Career Progression

Feb 2002 – Nov 2013

ZipRealty

Advanced from Transaction Coordinator to Help Desk Specialist to Help Desk Supervisor over 11 years — building the foundation in customer support operations, team supervision, and process improvement, including managing both internal agent support and a consumer-facing Client Services team.

    Get in touch

    If you’re building or scaling a support organization and looking to improve operations, efficiency, or strategy — I’d be happy to connect.