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Crypto Wallet Operations Specialist

DRW · Remote · Cumberland Ops & Wallets

Posted Sep 29, 2026 · We last checked this listing on Oct 6, 2026

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Likely interview questions for this role

Written from this job description, not a generic list. Each one notes what the interviewer is really checking.

About your past

Tell me about a time you improved an operational procedure.

What they are checking: Whether they refine workflows, which the posting names as part of the role.

Tell me about a mistake you made in an operations role and how you fixed it.

What they are checking: Honesty and quick escalation, which are vital when errors can be irreversible.

What would you do

A transfer to a counterparty has not arrived after an hour. What do you do?

What they are checking: Calm troubleshooting using block explorers and clear communication with the counterparty.

A trader urgently needs funds moved, but the request skips a normal approval step. What do you do?

What they are checking: Whether they hold to controls under pressure from the front office.

This role is ideally based in the Cayman Islands and works U.S. hours. How do you feel about that?

What they are checking: Whether they have seriously considered the location and schedule in the posting.

About the work

Walk me through how you would safely move a large amount of crypto between wallets and an exchange.

What they are checking: Whether they understand address checks, approvals and test transfers that prevent loss.

What is the difference between hot, warm and cold wallets, and when would you use each?

What they are checking: Core knowledge of custody tradeoffs between speed and security.

How do you guard against address poisoning or social engineering attacks?

What they are checking: Awareness of real threats to operations staff in crypto.

How do you reconcile on-chain balances with internal records each day?

What they are checking: Whether they can catch differences early before they turn into losses.

What blockchain networks and wallet tools have you worked with?

What they are checking: Hands-on familiarity with the networks and custody platforms used day to day.

Practice this interview out loud.

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The full job description

As published by DRW.

DRW is a diversified trading firm with over 3 decades of experience bringing sophisticated technology and exceptional people together to operate in markets around the world. We value autonomy and the ability to quickly pivot to capture opportunities, so we operate using our own capital and trading at our own risk. Headquartered in Chicago with offices throughout the U.S., Canada, Europe, and Asia, we trade a variety of asset classes including Fixed Income, ETFs, Equities, FX, Commodities and Energy across all major global markets. We have also leveraged our expertise and technology to expand into three non-traditional strategies: real estate, venture capital and cryptoassets. We operate with respect, curiosity and open minds. The people who thrive here share our belief that it’s not just what we do that matters–it's how we do it. DRW is a place of high expectations, integrity, innovation and a willingness to challenge consensus. As a Crypto Wallet Operations Specialist , you’ll help support the day-to-day operations of our cryptoasset trading business. You will work closely with a variety of internal teams and external counterparties and exchanges to efficiently manage daily workflows and continually refine operational procedures.  This role will work US hours and ideally be located in the Cayman Islands.  We will assist with relocation if needed.  For candidates with certain backgrounds, we may be open to London and Amsterdam.  Responsibilities • Facilitate cryptocurrency transactions between exchanges • Perform treasury and inventory management of Cryotoassets • Monitor pending settlements and liaise with counterparties and exchanges as needed to reduce settlement risk • Liaise with back-office teams to facilitate comprehensive reconciliation activities • Collaborate with a fast-paced trading team • Provide timely and accurate responses to internal and external requests • Pro-active problem-solver by being able to troubleshoot issues/problems • Utilize technology skills (Excel, VBA or other programming background) to automate operational processes and perform analysis on large data sets • Provide additional administrative support to the team as needed Requirements • Previous experience transacting cryptocurrency • Strong understanding various blockchains and how to read block explorers • Familiarity with centralized exchanges • Efficient in managing multiple tasks simultaneously • Experience with DeFi protocols highly preferred • Python experience preferred or other experience with scripting languages such as Excel or VBA • Traditional Finance or Crypto trading knowledge • Ability to work a variable work schedule that overlap with North America hours For more information about DRW's processing activities and our use of job applicants' data, please view our Privacy Notice at  https://drw.com/privacy-notice . California residents, please review the California Privacy Notice for information about certain legal rights at https://drw.com/california-privacy-notice . [#LI-SK1]  

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