Open to opportunities

Crystal Fleming

@crystalfleming

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Customer Success leader driving retention, expansion, and enterprise SaaS adoption.

United States

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What I'm looking for

I seek a senior/customer-success leadership role where I can drive retention, scale VOC programs, mentor teams, and deliver measurable ROI while working cross-functionally in a collaborative culture.

I am a seasoned Customer Success leader with extensive experience owning lifecycle outcomes for Enterprise customers across Oil & Gas, healthcare, and hospitality verticals. I build cross-functional teams, develop Voice of the Customer programs, and drive multi-year renewals and subscription growth.

I have a proven track record of improving retention and expanding accounts—achieving a 15% increase over retention goals and upgrading 25% of a portfolio from annual to multi-year agreements. I create onboarding playbooks, mentor new CSMs, and represent brands at conferences and webinars.

I thrive in both start-up and established environments, launching global support operations, implementing platforms like Gainsight, and driving product adoption through customer advocacy and data-driven programs. I prioritize measurable ROI, strong executive relationships, and sustainable customer value.

Experience

Work history, roles, and key accomplishments

Current

Self-employed Consultant

Current

Self-employed Consultant

Jul 2005 - Present (20 years 2 months)

Advised C-level clients on SaaS product adoption, built customer success processes and VOC programs, and led recruitment, training, and organizational design for startups and established companies.

Consulting VoC Program Recruitment Customer Advocacy Event Planning

Manager, Client Success

Exiger

Oct 2023 - Jul 2025 (1 year 9 months)

Owned enterprise customer success for Oil & Gas clients, managing lifecycle from implementation to renewal and aligning compliance, cybersecurity, and IT risk with business objectives to drive subscription growth.

Customer Success Account Management Risk & Compliance Stakeholder Management Mentoring

Senior Customer Success Manager

RiskOptics

Apr 2021 - Sep 2023 (2 years 5 months)

Managed enterprise customer lifecycle from pre-sale to renewal for cybersecurity customers, achieving retention 15% above goal and upgrading 25% of portfolio to multi-year agreements across nine quarters.

Customer Success Retention Renewals Stakeholder Engagement SaaS Onboarding Mentorship

Account Success Manager

Allen Technologies

Jan 2019 - Dec 2020 (1 year 11 months)

Led cross-functional teams to improve patient experience through adoption of patient engagement systems, overseeing training, project management, and C-level collaboration to drive customer outcomes.

Patient Engagement Customer Training Project Management Salesforce HubSpot Zendesk Cross Functional Team Management Case Study Development

Director of Customer Success

InforcePRO

Jun 2015 - Dec 2018 (3 years 6 months)

Launched and led Support and Customer Success teams in Austin and Gurgaon, implemented Gainsight, and developed end-to-end customer lifecycle programs to drive advocacy, retention, and product improvements.

Customer Success Leadership Gainsight Lifecycle Management Onboarding Customer Advocacy Salesforce

Department Manager, Customer Success

HotSchedules

Dec 2009 - Jun 2015 (5 years 6 months)

Drove customer loyalty and value delivery, managed Customer Success team development, and partnered with C-level clients to define goals and best practices, contributing to multiple vendor and sales awards.

Team Management Training SaaS Support Salesforce Zendesk Process Improvement