Leading remote teams and embracing technology as a competitive advantage

Executive overview

Most companies are behind on technology adoption and remote team cohesion — and both failures are now existential. Cameron Herold argues that vivid vision alignment and deliberate in-person gatherings replace what the office used to do, while aggressive AI adoption replaces experience-based seniority.

The COO is now the person who makes vision real — and must be technically competent to do it.

Ignoring AI isn't neutral; it's how you become the next Blockbuster.

Remote work and in-person cadence

• COVID normalised remote but didn't solve human connection — it shifted the problem
• In-office gatherings are now the new off-sites: getting together is as important as it once was to leave
• Cadence matters less than purpose — annual and quarterly planning sessions are the priority for in-person
• Small teams: rent an Airbnb rather than hotel rooms to rebuild informal connection
• COO Alliance event (2.5 days in-person) scored Net Promoter Score of +80% — far above typical online events
• Live communities will grow in value as remote becomes default and human connection becomes scarce

Culture and alignment in distributed teams

• Culture starts with alignment: vivid vision, core values, BHAG, core purpose — not office proximity
• A written vivid vision (3-year future description) lets every employee reverse-engineer toward the goal without being co-located
• Technology can amplify culture once alignment exists — not before

The CEO–COO relationship

• CEO holds the vision; COO makes it happen — "vision without execution is hallucination" (Thomas Edison)
• COOs complement CEO weaknesses; misalignment on core values makes the pairing fail
• The same person can be the wrong COO for one season and right for another — it depends on what the business needs
• COO Alliance: scorecard for CEOs to rate their second-in-command across 8 areas; self-assessment for COOs
• Book The Second in Command covers finding, onboarding, and building the CEO–COO relationship

Technology and AI adoption

• "If the rate of change outside your business is greater than inside, you're out of business"
• Southwest Airlines December 2022: planes and pilots were fine — an archaic booking system collapsed the entire operation
• 25-year-olds with 2 years of experience and strong tech skills outperform 60-year-olds with "40 years" of repeated experience
• Leaders must ask younger employees to teach them — not pretend to have it figured out
• One practical approach: task IT with replacing 12 expenses with 12 free software solutions over 12 months, then repeat
• COOs now need direct technical competency, not just someone who manages a tech person
• 4,000 AI tools exist; using even a subset to cut 10–30% of task hours compounds significantly over time

Tax, regulation, and global business environment

• Only two countries tax worldwide income: USA and Eritrea — a material constraint for international founders
• Dubai is aggressively entrepreneurial: modern infrastructure, low taxes, fast adoption of technology
• US regulatory regime (financial services, AI, content) is lagging — average Congress member "barely figured out email"
• Companies with innovative financial models are moving offshore because US compliance complexity is prohibitive