Cole McIlvaine

About Cole McIlvaine

I lead enterprise strategy and business operations initiatives that drive revenue growth, margin expansion, and operating discipline across $1B+ business lines.My work focuses on revenue model transformation, capital allocation, pricing strategy, and operating model design — translating enterprise growth ambitions into measurable financial outcomes. I’ve led initiatives that scaled a new monetization model to $500M annually, expanded it by an additional $174M in incremental cross-sell revenue, and reframed a $4.6B revenue opportunity that reset enterprise growth priorities and redirected 50% of engineering capacity toward revenue-generating initiatives.I operate at the intersection of commercial strategy and execution. That includes building pricing models and unit economics frameworks, aligning executive stakeholders around tradeoffs and investment priorities, and embedding governance, performance management systems, and cross-functional operating cadences that sustain growth beyond initial transformation.At Zillow, I led business model transitions, post-acquisition integration of a SaaS platform across partners, and enterprise planning processes spanning 1, 3, and 5 year forecasts presented at the executive and board level. My focus is not only launching new initiatives, but institutionalizing the systems, accountability, and leadership capability required to operate them at scale.I’m particularly energized by roles partnering with CEOs, Presidents, and senior leadership teams where enterprise transformation, revenue growth, and operating clarity are the mandate — including Head of Strategy & Operations, Chief of Staff, and GM-track leadership roles within complex, scaling organizations.Key Results Built and scaled a $500M monetization model; expanded by $174M through cross-sell growth Redirected 50% of engineering investment toward a $4.6B revenue opportunity Delivered recurring revenue and margin expansion across multiple business lines Led enterprise SaaS integration across B2B partners (35% → 100% adoption) Institutionalized multi-year strategic planning at executive and board level Developed and advanced 10+ team members while earning top manager engagement ratings (4.8/5) If you have a business to grow lets connect 🤝

Experience

1. Director, Strategy & Operations

   Open to opportunities

   Jan 2026 — Present

   Senior strategy and operations leader exploring Director, Senior Director, and Chief of Staff roles partnering with executive teams to drive revenue growth, operating model transformation, and enterprise performance.Experience leading revenue model redesign, pricing strategy, capital allocation decisions, and cross-functional execution across $1B+ business lines. Scaled a new monetization model to $500M annually, expanded it through $174M in incremental cross-sell revenue, and redirected engineering investment toward a $4.6B growth opportunity by embedding disciplined governance and operating rhythms.Most aligned to roles requiring commercial judgment, executive partnership, and structured execution across complex, scaling organizations.

Education

• D'Amore-McKim School of Business at Northeastern University

  Master of Business Administration - MBA, Finance, General

  2016

• University of Puget Sound

  Bachelor of Arts (B.A.), Business and Economics