Whether a family invests in digital assets is the family's decision. But once it does, even a small allocation brings operational demands that many traditional investment and operations hires have never had to manage. Hiring the right person — or deciding that a new hire isn't needed — starts with understanding what the work actually involves.
First, decide what kind of help the family needs
Not every allocation calls for a dedicated leader. A modest, long‑term position may be handled well by an existing CIO or COO working with a qualified custodian and outside advisors. An active strategy — trading, lending, or multiple venues and assets — usually needs someone in‑house who does this full time. Settling this question first keeps the family from over‑hiring, or from asking a generalist to manage risks they haven't seen before.
What the role actually involves
Digital assets carry responsibilities that traditional portfolios don't:
Custody: who holds the keys, how access is controlled, and when a qualified custodian is the better choice than holding assets directly.
Counterparty risk: where assets sit and how much is exposed to any one exchange or lender. The exchange and lender failures of 2022 showed what concentration can cost.
Round‑the‑clock markets: digital assets trade 24 hours a day, every day, which changes how positions are monitored and how controls are set.
Reporting and governance: valuation, accounting, tax reporting, and clear rules on who can approve what.
What separates strong candidates
Enthusiasm is easy to find; discipline is not. The candidates worth hiring talk about risk before return, can explain custody and counterparty decisions in plain language, and have built controls, not just placed trades. Experience through a serious downturn matters. Someone who managed positions or operations through 2022 has already been tested in the conditions a family most needs to protect against.
Where they come from
Good candidates come from digital‑asset trading firms and market makers, the crypto desks of traditional trading firms, custodians and exchanges (especially their operations, risk, and compliance teams), and funds with established digital‑asset strategies. Several Chicago trading firms run digital‑asset desks alongside their traditional markets, which makes the region a natural place to look.
Pay and structure
Candidates from digital‑asset firms may hold token‑based compensation or equity in private companies, often with vesting schedules. Understanding what a candidate would leave behind — and when it vests — is essential to building an offer they can accept.
Planning a leadership hire, even one that's months away? Start a confidential conversation.