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.
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.
Operational Systems & Tools
Examples of how I design systems to improve support operations, team performance, and decision-making.
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 2026Anywhere 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.
- Led escalations, incident management, service requests, and problem management
- Improved CSAT while increasing ticket volume and operational complexity
- Reduced MTTR for incidents and service requests
- Drove AI-enabled operational transformation through ServiceNow NowAssist
- Built support analytics, dashboards, playbooks, and knowledge-management systems
Director, Customer Support
Aug 2019 – Aug 2021Anywhere Real Estate · Emeryville, CA
Led Tier 2 customer support operations with accountability for KPIs, SLAs, and quality, focusing on escalation reduction, workflow optimization, and cross-functional collaboration with engineering and product teams.
- Owned KPIs including CSAT, SLA attainment, and quality performance
- Reduced L3 escalations through training, workflow redesign, and collaboration
Sr. Manager, Customer Success
Mar 2016 – Aug 2019Anywhere Real Estate · Emeryville, CA
Managed Tier 3 support and high-severity enterprise escalations while administering and optimizing Zendesk to improve case routing, reporting accuracy, and executive-level visibility into customer issues.
- Led Tier 3 support and enterprise escalations
- Optimized Zendesk routing and reporting for Success and Support teams
Early Career Progression
Feb 2002 – Nov 2013ZipRealty
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 that led to promotion into support management in 2013.
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.