Chris Riccio - VP of Engineering

Chris Riccio

VP of Engineering | Platform & Data Infrastructure Leader

Transforming engineering organizations through platform modernization, team scaling, and operational excellence
30+ years building reliable systems | 99.999% uptime | Led teams 5-50+ engineers

About

I specialize in taking engineering organizations through critical inflection points: scaling teams from 10 to 50+ engineers, migrating legacy systems to cloud architectures, establishing SRE practices and operational excellence, and navigating M&A integrations and organizational change.

I partner with CEOs and product leaders to align technical strategy with business outcomes, building engineering cultures where teams do their best work through better processes, clearer architecture, and stronger collaboration.

Platform Reliability

99.999% uptime achieved, reducing production outages from 12-24/year to fewer than 2/year

Performance Optimization

90% reduction in data processing latency (10 minutes to <1 minute)

Team Retention

100% team retention through COVID transition and M&A integration

Release Velocity

4-20x improvement in release cadence across multiple organizations

Cost Management

10% cloud infrastructure cost reduction while scaling 3x

Compliance & Security

Led SOC 2 Type 2 certification, removing critical sales bottlenecks

Featured Transformations

Platform Reliability at Scale

Uplevel | VP Engineering | 2022-Present

Challenge:

Developer productivity platform experiencing frequent outages impacting 50,000+ engineers across enterprise customers. Production incidents occurring 12-24 times per year with extended resolution times.

Solution:

Built SRE function from zero, implemented infrastructure-as-code using Terraform, established on-call practices and incident management processes, migrated CI/CD to GitHub Actions, transitioned AWS infrastructure to multi-account organization.

Results:

Achieved 99.999% platform uptime | Reduced outages from 12-24/year to <2/year | Decreased cloud costs by 10% while scaling data volume 3x | Reduced incident resolution time from hours to minutes

Acquisition Integration & Product Pivot

Zipwhip/Twilio | Director Engineering | 2018-2022

Challenge:

Navigate Twilio acquisition of Zipwhip while maintaining team cohesion and pivoting from Zipwhip product to Twilio Messaging Insights product. Risk of team attrition during major organizational change.

Solution:

Built 7-engineer analytics team from zero supporting company strategy and thousands of enterprise users. Led team through COVID remote transition and acquisition integration. Delivered BI platform powering executive dashboards and customer-facing reporting for platform processing billions of SMS messages.

Results:

100% team retention through two major transitions | Successful pivot to new product in 90 days | Delivered reporting platform powering company SOAP metrics (ARR, customer growth) | Supported thousands of insurance agents with mission-critical reporting

Release Velocity Transformation

FTI Technology | Senior Director Engineering | 2015-2018

Challenge:

Ringtail e-Discovery platform releasing only twice yearly, causing customer upgrade pain with days of downtime and 6+ month delays for new features to reach customers.

Solution:

Led distributed engineering organization (15-18 engineers across Seattle and Pittsburgh). Established engineering metrics culture, implemented trunk-based development, improved CI infrastructure, modernized DevOps practices (TFS to Git/GitHub, AWS-hosted Jenkins).

Results:

Transformed release cadence from twice yearly to weekly deployments | Reduced customer upgrade downtime from days to hours | Improved CI build time by 50% | Delivered 45+ weekly releases with zero rollbacks | Drove code review adoption from 40% to 95%

Global Test Automation & Continuous Delivery

Expedia | Director of Technology | 2011-2015

Challenge:

Manual testing practices blocking continuous delivery across 900+ engineer global organization. Release velocity constrained by 60-90 minute regression test cycles.

Solution:

Architected test automation strategy for Expedia.com platform powering 100+ country sites. Built distributed test execution system, shifted organization from manual to automated testing, implemented test automation pyramid.

Results:

4x release velocity improvement (bi-monthly to bi-weekly) | Reduced test execution time from 60-90 minutes to <5 minutes | Launched 5 major loyalty programs in 2014 (Expedia+, Barclays, Nectar, Citi partnerships) | Influenced engineering practices across 900+ person global team | Promoted from Senior Engineer to Director based on transformation impact

Experience

VP, Engineering
Uplevel | Remote
August 2022 – Present

Lead engineering for developer productivity analytics platform processing 20TB of data serving 50,000+ engineers. Partner with CEO and VP Product on business strategy and technical architecture. Own $2M+ engineering budget.

Director of Engineering
Zipwhip (Acquired by Twilio) | Seattle, WA
October 2018 – August 2022

Built and led 7-engineer analytics team supporting company strategy and thousands of enterprise users. Delivered BI platform powering executive dashboards and customer-facing reporting for platform processing billions of SMS messages.

Senior Director, Technology
FTI Technology (Ringtail) | Seattle, WA
June 2015 – October 2018

Led distributed engineering organization responsible for developer tooling, automated testing, and product support for Ringtail e-Discovery platform serving corporate legal departments.

Director of Technology
Expedia Inc. | Bellevue, WA
June 2011 – June 2015

Drove test automation transformation across 900+ engineer global organization, enabling 4x release velocity improvement for Expedia.com platform. Promoted from Senior Engineer to Director based on impact.

Earlier Career
Microsoft, Nokia, Redfin, KIHA Software
1997 – 2011

Microsoft (1997-2008): Grew from IC to Senior Test Manager leading 20+ engineers across ASP.NET, IIS, and .NET Framework teams. Original member of XSP project (became ASP.NET). Contributed to foundational web technologies used by millions of developers.

Additional roles: Nokia (SDET Lead, Ovi cloud services), Redfin (Test Manager), KIHA Software (Test Architect)

Core Expertise

Leadership

Engineering Strategy
Platform Architecture
Team Scaling & Development
Process Transformation
M&A Integration
Budget Management
Stakeholder Management

Cloud & Infrastructure

AWS (Solutions Architect)
Infrastructure-as-Code (Terraform)
Site Reliability Engineering
CI/CD Pipeline Design
Docker & Kubernetes
GitHub Actions, Azure DevOps

Data & Platform

Data Platform Architecture
PostgreSQL, MS SQL Server
Azure Synapse Analytics
ETL/ELT Pipelines
Business Intelligence
Real-time Data Processing

DevOps & Quality

DevOps Transformation
Incident Management
Observability & Monitoring
Test Automation
Security & Compliance (SOC 2)
Release Engineering

Education & Certifications

Bachelor of Arts in Computer Science
New York University
AWS Solutions Architect – Associate
Amazon Web Services
Current