Customer Support Operations Leader
Michael Reagan
Designing scalable support systems through process, data, and AI.
Focused on improving efficiency, customer experience, and operational performance at scale.
Introduction
I design and improve customer support operations.
My focus is on building systems that scale — connecting process, data, and AI to improve efficiency, decision-making, and customer outcomes.
Operational Systems & Tools
Examples of how I design systems to improve support operations, team performance, and decision-making.
AI Support Operations Lab
Interactive system for modeling and improving support operations using AI
A simulation environment that connects support metrics to operational decisions, enabling leaders to test improvements and quantify business impact.
View Case Study →
Manager Development System
Structured framework for building high-performing support teams
A lightweight system that helps managers assess performance, prioritize development areas, and track progress through structured coaching and action planning.
View Case Study →About
I focus on designing and improving customer support operations.
My experience centers on identifying operational friction, optimizing workflows, and improving both customer outcomes and team efficiency.
I approach support as a system — one that can be designed, measured, and continuously improved.
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 (Level 2)
Aug 2021 – Mar 2026Anywhere Real Estate · Emeryville, CA
Led a Tier 2 customer support organization of approximately 30 employees, including 3 direct-report leaders, supporting tens of thousands of customers 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
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.