Gregg Colacichi

Customer Success leader with 8+ years of SaaS experience driving enterprise retention, adoption, and value realization, supported by deep technical success and enterprise technology leadership expertise. Proven record leading global customer-facing teams, managing $43M ARR portfolios, improving retention, scaling Customer Success programs, and delivering measurable outcomes for Fortune 500 organizations. Experienced in building and maturing Customer Success functions through customer health programs, renewal forecasting, executive stakeholder engagement, success planning, escalation management, and cross-functional leadership.

Recognized for combining business acumen with technical depth to improve retention, accelerate adoption, and create long-term customer value.

Senior Manager, Customer Success at Lakeside Software (2022-01 – Present)

Lead a global customer-facing organization focused on adoption, retention, value realization, and strategic account engagement for enterprise and Fortune 500 customers.

• Lead and develop a global team of 7 customer-facing professionals across North America and EMEA, supporting 372 enterprise customers and approximately $43M ARR
• Achieved and maintained 91% gross retention through proactive risk identification, executive alignment, and structured success planning across strategic enterprise accounts
• Built and managed the operating cadence for a global Customer Success team, including account health reviews, renewal forecasting, onboarding governance, escalation management, and executive business review standards
• Standardized success playbooks, account planning processes, and engagement frameworks to improve consistency, scalability, and visibility into churn risk and growth opportunities
• Reduced customer issue resolution times by approximately 40% through process improvements, clearer escalation paths, and stronger cross-functional collaboration with Product, Engineering, Sales, and Support
• Established Voice of Customer processes that translated customer feedback into product enhancements and roadmap prioritization
• Implemented AI-enabled workflow automation using Claude, Aisera, Microsoft Copilot, and Google Gemini to reduce manual reporting and administrative work, reclaiming approximately 2 months of cumulative annual team capacity for higher-value customer engagement

Client Success Manager at Lakeside Software (2021-01 – 2022-12)

Managed strategic enterprise customer relationships across a $43M ARR portfolio, developing success plans aligned to customer business objectives, adoption goals, and measurable outcomes

• Led executive stakeholder relationships across Fortune 500 organizations and served as escalation leader for at-risk accounts, coordinating recovery plans across Sales, Product, Support, and Engineering
• Improved retention and expansion opportunities through structured health monitoring, lifecycle engagement, and proactive risk mitigation

Customer Success Engineer at Lakeside Software (2021-01 – 2021-12)

Led technical onboarding and implementation efforts for enterprise customers, accelerating time-to-value and improving early-stage adoption

• Developed repeatable onboarding methodologies that improved implementation consistency and aligned technical delivery to customer business objectives

Technical Account Manager at Lakeside Software (2018-01 – 2021-12)

Managed strategic enterprise customer relationships as a trusted advisor for adoption planning, platform optimization, and long-term customer success across complex environments

• Supported strategic account planning and executive customer engagements by aligning platform capabilities to business priorities and customer outcomes

Associate – Systems Administration at JPMorgan Chase (2014-01 – 2018-12)

Led an 8-person engineering team supporting 50,000+ enterprise endpoints across a global financial services environment

• Improved service reliability, security compliance, and operational efficiency through infrastructure optimization, SOP development, and process improvement initiatives
• Reduced operational costs by more than $1M through technology standardization and operational improvements across distributed infrastructure environments

AVP – Infrastructure & Server Administration at Bank of America (2010-01 – 2014-12)

Led global teams supporting 16,000+ servers and 9,000+ virtual machines across highly regulated enterprise environments

• Directed compliance-driven infrastructure operations and service delivery across onshore and offshore teams supporting mission-critical banking systems

Head of Technology at Trafelet Delta Funds (2008-01 – 2010-12)

Built and led technology operations for U.S. and London offices, overseeing infrastructure, service delivery, vendor management, and disaster recovery planning

• Reduced technology costs by approximately $700K through strategic sourcing, vendor negotiation, and operational improvements

Progressive Leadership Positions at Various

Held progressive leadership positions in enterprise infrastructure, trading systems, technology operations, and IT management with Computer Sciences Corporation (sole account worldwide unaffected by the Code Red virus), CE Unterberg Towbin, Pequot Capital Management, and Columbus Avenue Consulting.

B.A. in Business Management – Berkeley College

A.A. in Business Administration – Middlesex County College