Consulting for decisions that matter
About Clever Moontrail
The outside perspective is often more useful than the inside one.
Clever Moontrail started in 2000 with one retained client, a software company in the South of Market neighborhood of San Francisco that needed help thinking through its first real organizational structure. Colin Caldwell had spent the previous several years working inside companies on strategy and…
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ContactWhat this practice does
Strategic clarity
Working through the decisions that keep getting deferred. Not a slide deck. A working document you can return to.
Organizational design
How the work is structured, who owns what, and where the friction is. Useful when a team has grown faster than its processes.
Decision frameworks
Building repeatable ways to evaluate options, so the same conversation does not happen three times a year.
Recent writing
- 012026-10-01
When a Strategy Problem Gets Treated as a Planning Problem
There is a specific kind of meeting that happens in organizations every quarter. The agenda says…
- 022026-08-24
Organizational Design When Your Team Doubles in Two Years
A team of eight can operate on shared understanding. Everyone knows what everyone else is doing,…
- 032026-07-01
Decision Frameworks That Teams Actually Use After the Consultant Leaves
Most organizations have more frameworks than they use. The strategy offsite produces a…
"Colin Caldwell has run Clever Moontrail as a solo consulting practice since 2000, working with founders and leadership teams on organizational strategy, decision-making frameworks, and operational clarity. He takes on a small number of clients at a time, working closely through each engagement rather than handing off to a junior team. The practice started with a single retained client in the Bay Area and has grown steadily through repeat work and referrals from that same network. Today Colin splits his time between client sessions, written strategy documents, and occasional workshops for leadership groups."
Get in touch
Tell Colin what you are working on
Colin reads every message and responds within 2 business days. If the situation fits, he will suggest a time for a first conversation.