DAVID STUDEBAKER
Enterprise Customer Success → AI Workflow Transformation

David Studebaker

Enterprise Customer Success Leader | Building Practical AI & Agentic Workflow Expertise

14+ years leading enterprise Customer Success, renewals, and transformation programs for Fortune 500 organizations — now applying that operating experience to AI adoption: building agentic workflows, RAG-based knowledge assistants, and governance frameworks that help SaaS and CS organizations deploy AI responsibly and measurably.

Loomis, CA dstudebaker@gmail.com (707) 239-0642 LinkedIn ↗ dstudebaker.com ↗
Agentic Automation RAG & Evals AI Governance & Risk Enterprise SaaS

About

Professional Summary

Enterprise Customer Success leader with 14+ years of experience helping Fortune 500 and enterprise organizations achieve measurable business outcomes from strategic software investments. Proven track record leading executive stakeholder engagement, enterprise transformation initiatives, customer adoption programs, renewals, expansion opportunities, and global SaaS implementations. Trusted advisor to Engineering, Product, Platform, and Technology leaders, translating enterprise software capabilities into measurable business outcomes. Currently extending this expertise into applied AI — building and shipping agentic automation, knowledge assistants, and governance frameworks purpose-built for Customer Success and Support organizations.

Enterprise Customer Success Strategic Accounts Executive Relationship Management Customer Lifecycle Management Renewals & Expansion Executive Business Reviews Value Realization Cross-Functional Leadership Agile & Portfolio Management AI Adoption Agentic Workflows RAG & Knowledge Assistants AI Governance & Risk

Experience

Professional Experience

Director, Customer Success
Jun 2017 – Present
Planview (formerly Plutora)
  • Own the Customer Success strategy for a portfolio of Enterprise accounts across North America, representing approximately half of the company's recurring revenue, serving as executive sponsor for strategic customers.
  • Own the full customer lifecycle, including onboarding, adoption, value realization, governance, renewals, and expansion.
  • Maintained approximately 85% annual gross retention while partnering with Sales to identify expansion opportunities and improve long-term customer value through executive engagement, adoption planning, and proactive risk management.
  • Directed Customer Success, Solution Consulting, and Professional Services functions within the U.S. region, leading a team of up to five customer-facing professionals.
  • Developed global implementation frameworks, customer health methodologies, and risk management processes that accelerated time-to-value while improving visibility into adoption, stakeholder alignment, and expansion opportunities.
  • Conduct executive business reviews that align platform capabilities with customer business objectives, reinforce measurable value realization, and strengthen renewal readiness.
  • Partnered closely with Product Management and Engineering to advocate for customer needs, influence roadmap discussions, and coordinate executive escalations to resolve complex customer challenges.
  • Supported strategic enterprise opportunities during periods of increased pre-sales demand, partnering with Sales on discovery workshops, executive presentations, solution demonstrations, and business value discussions.
  • Guided enterprise customers through organizational and process transformation initiatives supporting long-term platform adoption and business outcomes.
Solution Consultant (Post-Sales)
Jun 2015 – May 2017
Plutora
  • Led post-sales discovery workshops, executive strategy sessions, solution demonstrations, implementation planning, and business value assessments for enterprise customers.
  • Delivered successful enterprise SaaS implementations for customers across multiple industries and geographies.
  • Generated over $1M in Professional Services revenue through strategic consulting and implementation engagements.
  • Bridged pre-sales and post-sales activities, creating continuity between solution evaluation, implementation, adoption, and long-term customer success.
Project Manager, Agile Coach, Scrum Master
Dec 2010 – Dec 2014
Cisco Systems
  • Managed complex cross-functional enterprise software initiatives spanning Product, Engineering, Operations, and Services organizations while coaching Agile teams and improving delivery execution.
  • Provided Agile coaching and transformation leadership across enterprise programs and delivery teams.
  • Partnered with executive and operational leaders to improve planning, execution, organizational effectiveness, and customer outcomes.

Education

Education & Continued Learning

Bachelor of Science, Information Systems Management — University of California, Santa Cruz
Bachelor of Arts, Business Management Economics — University of California, Santa Cruz
In Progress: Applied AI & Agentic Automation certificate program — Anthropic Academy, OpenAI Academy, Microsoft AI Transformation Leader (target completion: Q3 2026)