Keagan Pennycuff

About Keagan Pennycuff

I’m an executive-level Product and Strategy Leader with 12+ years in Big Tech, specializing in large-scale Quote-to-Cash (QTC) transformation, M&A integration, and enterprise SaaS operational design. My career has centered on solving complex, cross-functional problems—aligning product, engineering, sales, finance, and compliance teams to deliver systems that scale globally and accelerate revenue outcomes.I have deep expertise across the Salesforce ecosystem, including CPQ, Billing, Revenue Cloud, and RevRec, and I’ve led multiple multi-billion-dollar programs spanning product roadmapping, SOX-compliant process design, automation, and post-merger integration. My work includes driving 85%+ automation for acquired product lines, steering global transformation initiatives, and influencing executive sponsors to define and deliver key design decisions.I’m passionate about bridging strategy and execution—bringing clarity to ambiguity, building high-performing teams, and creating user-centric systems that deliver measurable impact. Whether leading enterprise-wide QTC redesigns or guiding innovation initiatives, I focus on reducing friction, accelerating time-to-value, and enabling sustainable, scalable growth.

Experience

1. Senior Manager, Revenue Growth & Automation

   Salesforce

   Aug 2022 — Present

   Directed global Quote-to-Cash transformation programs, providingexecutive-level reporting, partnering with cross-functional teams to alignstrategies, and delivering process improvements to Revenue Cloud and CPQplatforms for enhanced efficiency and customer success.

Education

• Indiana University Indianapolis

  Bachelor of Science in Public Affairs, Management

  2011 — 2014

Skills

• Coordinate Meetings
• Customer Service
• Outreach Services
• Project Management
• Data Analysis
• Training & Development
• Performance Reporting
• System Deployment
• System Administration
• Document Drafting
• Analysis
• Functional Testing
• Cross-Functional Coordination
• Leadership
• Qualitative Research
• Interpersonal Communication
• Public Administration
• Presentation Skills
• Documentation
• Public Engagement
• Ad Hoc Reporting
• Elections
• Live Meeting
• Enterprise Software
• Voting Systems
• Meeting Planning
• System Testing
• Performance Testing
• Troubleshooting
• Public Speaking
• Document Management