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Falls Church, VA 22046
Linkedin: linkedin.com/in/lindsaycregger

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PROFESSIONAL SUMMARY 

Strategic and process-driven Vice President of Customer Success with 15+ years of leadership experience building and scaling CS organizations from the ground up across SaaS in both private and public sectors. Proven success in architecting high-impact playbooks, onboarding frameworks, team structures, and tech stacks that drive 90%+ renewal rates, accelerate time to value, and improve operational efficiency. Trusted leader with a passion for transforming CS into a strategic growth engine. 

AREAS OF EXPERTISE 

  • CS Operations Strategy & Execution 
  • Tech Stack Optimization (Planhat, HubSpot, Pendo) 
  • Process Design Across the Customer Journey 
  • Health Score Frameworks & Risk Modeling 
  • Data-Driven Insights & Dashboards 
  • Scalable Playbooks & Enablement 
  • Segmentation: High-Touch, Digital, Low-Touch 
  • KPI Development (NRR, GRR, CSAT, CES, TTV) 
  • Onboarding & Implementation Optimization 
  • Cross-Functional Alignment (Product, Sales) 
  • Internal Enablement & CS Training 
  • Churn Analytics & Root Cause Analysis 
  • Workflow Automation & Efficiency 
  • Expansion & Retention Forecasting 

PROFESSIONAL EXPERIENCE 

Vice President of Customer Success, Federal | Decision Lens – Arlington, VA | Sep 2021 – Jun 2025 

  • Maintained a 90%+ renewal rate across a $15M+ federal portfolio through success planning and value delivery 
  • Contributed to doubling ARR from $9M to $18M over 3 years, leading to PE acquisition 
  • Built CS function from scratch, scaling team from 4 to 9 and creating playbooks aligned to government lifecycles 
  • Launched structured onboarding program reducing time to productivity by 50% 
  • Grew customer base 4x (10 to 45+ accounts) while preserving high-touch service through operational redesign 
  • Deployed Planhat to automate workflows, boosting CS efficiency by 35% 
  • Drove 2x increase in product training participation through CS-led webinars
  • Increased services upsell by 20% through monetized onboarding and success planning 

    Vice President of Customer Success | Fedmine – Rockville, MD | Sep 2016 – Sep 2021 

    • Built a full-lifecycle CS function serving 100+ federal SaaS clients 
    • Achieved a 95% renewal rate through structured workflows and engagement models 
    • Led $1M+ VA contract as project lead, building CS models tailored to federal procurement 
    • Integrated CS insights into product planning, improving roadmap velocity and adoption 
    • Created onboarding/training materials used by Sales and Marketing to streamline activation 

    Strategic Social Partnerships Consultant | Oracle – San Francisco, CA | Jan 2015 – Jun 2015 

    • Managed enterprise clients (Clorox, Kohl’s, Vans, YouTube) through onboarding, training, and adoption 
    • Served as trusted advisor to senior stakeholders, aligning product use to business goals 
    • Collaborated cross-functionally to resolve issues, reducing time-to-value by 30% 
    • Improved NPS by double digits through strategic advisory and platform optimization 

    Enterprise Customer Success Manager | Govini – San Francisco, CA | Oct 2013 – Dec 2014 

    • Developed scalable CS playbooks for onboarding, QBRs, and retention 
    • Promoted to Enterprise AE after achieving 200% of quota in two months 
    • Created demo and lifecycle content adopted across departments 

    Senior Account Manager | Deltek – Herndon, VA | Oct 2010 – Oct 2013 

    • Created and delivered onboarding/training curriculum for new hires 
    • Managed 100+ client relationships, driving 95%+ retention through proactive engagement 

    Client Services Representative | IntraFi – Arlington, VA | May 2009 – Oct 2010 

    • Supported high-volume onboarding and internal training on proprietary systems 

    EDUCATION 

    Virginia Tech, Pamplin College of Business – Blacksburg, VA 

    B.S., Marketing Management, May 2005 

    Study Abroad: American Intercontinental University, London 

    CERTIFICATIONS 

    • Pavilion: Chief Customer Officer (CCO) School Graduate 
    • Planhat Certified Power User 
    • Active Top Secret Clearance 

    TECHNICAL SKILLS 

    Microsoft Office Suite, Google Workspace, Salesforce, HubSpot, Planhat, JIRA, Harvest, Asana, Pendo, Canva