Assistant General Counsel – Regulatory Affairs & Enforcement

Coinflip-; Chicago (IL); On-site; USD 180,000 - 220,000; Full time

Benefits offered by this job

Annual bonus

Unlimited PTO

Flexible work from home policy

Comprehensive benefits (medical,Dental

Vision, 401(k) with match

Job summary

CoinFlip seeks an experienced Assistant General Counsel to lead regulatory affairs and support the Chief Legal Officer on enforcement actions, litigation, and strategic legal initiatives. This role focuses on responses to examinations, licensing strategy, and cross‑functional regulatory guidance.

The ideal candidate is a former litigator with significant experience in financial services regulation, licensing, and compliance.

Qualifications

• JD from an accredited law school and bar membership.
• 7–10+ years of regulatory, money services, and fintech licensing experience.
• Experience managing outside counsel and complex regulatory matters.
• Background in financial services, fintech, or regulated industries.
• Strong drafting, analytical, and communication skills.
• Ability to operate independently while collaborating with senior legal leadership.

Responsibilities

• Manage CoinFlip’s responses to examinations by state financial regulators, from notice through closure.
• Serve as primary legal contact for regulators and represent CoinFlip in examinations and hearings.
• Lead legal strategy and response efforts for regulatory inquiries, subpoenas, and enforcement actions.
• Advise on state money transmitter laws and licensing frameworks, triggers, and exemptions.
• Partner with Licensing, Compliance, Risk, Operations, and Product teams on regulatory matters.
• Provide guidance on federal and state financial-services laws (BSA/AML, OFAC, privacy, etc.).
• Develop submissions to regulators and coordinate supporting facts, data, and documents.

Skills

Regulatory experience

Legal drafting

Communication skills

Independent work

Education

Juris Doctor (JD)

Job description

Description

CoinFlip is a global digital currency platform company, focused on providing consumers with simple and secure access to buy and sell cryptocurrency. The company operates the world's largest network of?cryptocurrency?kiosks by transaction volume with more than 5,500 kiosks the United States, Canada,?Australia,?New Zealand,?South Africa and?Italy. CoinFlip’s digital currency kiosks make buying and selling major?cryptocurrencies?accessible and safe for consumers who wish to purchase their digital currency using cash. CoinFlip also operates CoinFlip Preferred, a personalized over-the-counter service that provides investors with custom, white glove support for their cryptocurrency transactions. In 2022, CoinFlip launched CoinFlip Ventures, an investment group offering coaching, funding, and networking support to early-stage crypto and web3 projects. CoinFlip recently received authorization under the European Union’s Markets in Crypto-Assets Regulation (MiCA), marking an important milestone in the company’s continued expansion of regulated digital asset services across Europe.

Headquarters and Accolades

Headquartered in?Chicago, CoinFlip placed in the top 500 on the 2021, 2022, and 2023 Inc. 5000 list, and on the 2022 and 2023 Deloitte Technology Fast 500, was named the 2021 and 2022 #1 fastest-growing company in?Chicago?by Crain's, ranked in Chicago Tribune’s Top Workplaces in 2021 and 2022, and was awarded the 2021 and 2022 Stevie ® Awards for Customer Service. To learn more about CoinFlip and how to get started on your digital currency journey, visit www.coinflip.tech.

CoinFlip is seeking an experienced Assistant General Counsel to lead key regulatory affairs matters and support the Chief Legal Officer and General Counsel on enforcement actions, litigation, and strategic legal initiatives. This role will have primary legal responsibility for CoinFlip's responses to examinations by state financial regulators and will serve as a principal point of contact with regulatory agencies. It is an opportunity for a former litigator to apply strong advocacy, investigative, and case-management skills to the evolving regulation of money transmission and digital assets.

The Assistant General Counsel will interact directly and regularly with state and federal regulators, including in examinations, supervisory meetings, investigations, enforcement proceedings, and discussions concerning licensing and regulatory expectations. The attorney will coordinate cross-functional responses, develop clear and defensible legal positions, and guide matters from initial contact through resolution.

The ideal candidate is a former litigator with meaningful experience in financial services regulation, state money transmitter laws and licenses (MTLs), regulatory examinations, investigations, and enforcement actions. Trial or significant hearing experience is a plus. The attorney must be comfortable taking ownership of high stakes matters, communicating credibly with regulators, and translating legal and regulatory requirements into practical guidance for the business.

Responsibilities

• Have primary responsibility for managing CoinFlip’s responses to examinations by state financial regulators, from the initial examination notice and scoping through document productions, interviews, findings, remediation, and closure.
• Serve as a principal legal point of contact for state and federal regulators and represent CoinFlip in examinations, supervisory meetings, interviews, conferences, hearings, and other regulatory engagements.
• Lead legal strategy and response efforts for regulatory inquiries, subpoenas, civil investigative demands, investigations, enforcement actions, consent orders, and settlement negotiations.
• Advise on state money transmitter laws and domestic and international licensing frameworks, including licensing triggers and exemptions, permissible activities, examination standards, reporting obligations, and the regulatory implications of new products, transaction flows, business models, and market expansion.
• Partner with the licensing team on complex or novel legal and regulatory matters, including regulator interpretations and jurisdictional strategy, with clear coordination between legal advisory and licensing administration responsibilities.
• Provide legal guidance on federal and state financial-services laws, including BSA/AML, OFAC, consumer‑protection, privacy, money‑transmission, and digital‑asset regulatory requirements.
• Develop accurate, consistent, and persuasive written submissions to regulators and coordinate the collection and analysis of supporting facts, data, and documents.

Litigation & Dispute Management

• Own legal strategy for significant litigation, arbitration, and dispute‑resolution matters, including consumer, commercial, and regulatory disputes, from inception through resolution.
• Lead factual investigations, discovery, briefing, witness and executive preparation, depositions, hearings, negotiations, and trial strategy.
• Select, supervise, and manage outside counsel; establish strategy, maintain accountability, control costs, and ensure high‑quality legal representation.
• Advise the General Counsel and senior leadership on litigation exposure, enforcement trends, settlement strategy, remediation, and risk‑mitigation options.

Business and Regulatory Advice

• Advise business leaders and cross‑functional teams on regulatory and legal issues affecting CoinFlip’s products and operations, translating complex requirements into practical, risk‑based guidance.
• Partner with Compliance, Licensing, Risk, Operations, Product, and other business teams to interpret regulatory requirements, strengthen policies and controls, and address examination findings and emerging risks.
• Monitor legal and regulatory developments affecting crypto kiosks, OTC trading, money transmission, and digital‑asset services, and assess their impact on CoinFlip’s business.

Government Affairs

• Collaborate with the Government Affairs team on legislative and policy matters, including analyzing proposed laws and regulations, developing advocacy positions, drafting comment letters and testimony, and representing the company in meetings, hearings, and other proceedings involving legislators, policymakers, and regulators.

Other Responsibilities

• Support strategic legal and regulatory initiatives led by the Chief Legal Officer, General Counsel, or Global Head of AML.
• Perform other duties as assigned.

Qualifications

Required

• Juris Doctor (JD) from an accredited law school.
• Active bar membership in at least one U.S. jurisdiction (Illinois preferred or ability to obtain).
• 7–10+ years of relevant legal experience with regulatory, money services business, digital asset and money transmitter licensing experience.
• Proven experience managing outside counsel and complex regulatory matters.
• Background in financial services, fintech, or other regulated industries.
• Strong legal drafting, analytical, and communication skills.
• Ability to operate independently while collaborating closely with senior legal leadership.

Preferred

• In‑house or government experience involving a money services business, payments company, bank, fintech, cryptocurrency company, or financial regulator.
• Experience with BSA/AML, OFAC, consumer protection, unfair or deceptive acts or practices, privacy, and digital asset regulatory frameworks.
• Experience negotiating resolutions with regulators or advising high‑growth, technology‑driven companies through regulatory change.

Nice to have

• Basic knowledge of cryptocurrency and blockchains.
• General passion and knowledge of fintech and cryptocurrency.

Compensation

• $180,000 - $220,000 USD yearly salary
• Annual bonus
• Federal holidays and unlimited PTO
• Flexible work from home policy
• Comprehensive benefits (medical, dental, vision, 401(k) with match)
• Reimbursement for ARDC annual dues, professional organization expenses, legal conferences and CLEs

Working at CoinFlip means collaborating with experienced and innovative leaders who share a clear vision and a track record of success. We offer a collaborative and positive working environment where we encourage employees to balance productivity with time to recharge. Compensation is above and beyond a typical “startup” — we offer competitive salaries, performance‑based incentives, and competitive benefits for full‑time employees.

CoinFlip values diversity in the workplace and is an equal opportunity employer committed to providing an inclusive and accessible work environment. We thank all candidates who apply, but only those selected for an interview will be contacted.

By applying to this role, you give express consent to CoinFlip to send you informational text (SMS) messages regarding this role and the application process. You can cancel the SMS service at any time by replying "STOP" to the text message you received. If at any time you forget what keywords are supported, just reply "HELP." Message and data rates apply. If you require a special accommodation, please let us know and we’ll work with you to meet your needs.