Carolyn Reeves

About Carolyn Reeves

I help SaaS organizations navigate growth, change, and complexity by building the operating systems that make strategy executable.I’m a Product & Business Operations leader with experience guiding teams through post-acquisition integration, scaling, and enterprise-level change in private-equity-backed and high-growth environments. My work sits at the intersection of product, revenue, and customer teams - translating strategy into clear operating models, execution plans, and communication that actually hold up as organizations grow.I’m known for stepping into ambiguity, aligning senior stakeholders without formal authority, and bringing structure to areas where critical knowledge often lives in people’s heads. That includes building foundational processes for launch readiness, customer migrations, pricing and packaging changes, and roadmap visibility - often in environments where the work is still evolving and adoption takes time.Earlier in my career, I led programs and operations in mission-driven organizations, building financially sustainable models under real constraints. That experience continues to shape how I approach my work today: with a focus on clarity, accountability, and long-term impact.I’m most energized by roles where the mandate is to bring order to complexity during periods of growth or transition and where thoughtful operational work enables teams to do their best work.

Experience

1. Program Manager, Organizational Readiness

   insightsoftware

   Feb 2026 — Present

   Lead cross-functional initiatives focused on organizational readiness and execution for Tier 1 and 2 launches-Drive alignment between strategy and execution across Product, GTM, and leadership stakeholders-Establish structure, visibility, and operating rhythms to support delivery in complex, fast-moving environments-Identify and address gaps in planning, communication, and execution to improve how work lands across teams

Education

• University of Wisconsin-Milwaukee

  Master of Business Administration - MBA

  2018

• University of Wisconsin–Oshkosh

  Bachelor of Arts - BA, International Studies, Spanish

  2008

Skills

• Program Development
• Spanish
• Public Speaking
• Service Coordination
• Cost Accounting
• Department Budgeting
• International Development
• Event Planning
• Copy Editing
• Government
• Spanish-Speaking
• Strategic Planning
• Project Management
• Research
• Microsoft Office
• Proposal Writing