Operating Groups Layer Management

Andrew Wilkinson shares how he structures his portfolio of 40 companies through operating groups, allowing him to effectively manage multiple businesses without direct involvement in day-to-day operations.

Key Structure:

  • Create operating groups that cluster similar businesses together
  • Each operating group has its own CEO who oversees multiple portfolio companies
  • Operating group CEOs report directly to ownership
  • Example: Digital services businesses are grouped under one operating head who oversees 6 companies

Benefits:

  • Reduces number of direct reports to ownership
  • Creates manageable spans of control
  • Allows scaling beyond 5-6 direct CEO reports
  • Enables hands-off ownership while maintaining oversight
  • Meetings with operating heads occur biweekly/monthly as needed

Communication Flow:

  • Portfolio Company CEOs → Operating Group CEO → Owner
  • Some CEOs haven't spoken to owner in 2-3 years
  • Operating heads handle regular oversight and management
  • Owner only needs to meet with operating group leaders periodically

This structure evolved from initially having 5 direct CEO reports to now managing 40 companies through operating group layers, making the portfolio more scalable and manageable.

04:09 - 04:38
Full video: 57:14
AW

Andrew Wilkinson

Co-founder of Tiny

Wilkinson is the co-founder of Tiny Capital, which owns companies including AeroPress, MetaLab and Dribble. He is also the co-founder and chairman of WeCommerce, a holding company that starts, buys, and invests in the world’s top Shopify businesses.

TwitterLinkedIn
Founder
Author
Investor