Assistant Counsel Jobs in Chicago, IL

At Koalafi, we believe in a world where no one has to put an important purchase on hold. That's why we're making it easier for more people to pay for big purchases over time.

Retailers across the country rely on us to offer flexible lease-to-own financing to their non-prime consumers, while increasing sales and strengthening customer loyalty. Their 2M+ customers love us because we provide a flexible way for them to make payments and give them an opportunity to improve their credit. Our 200+ Koalafi teammates enjoy inspiring and challenging work that accelerates their careers.

Interested in learning more about how we're transforming the financing experience and joining our team?

Assistant General Counsel

Koalafi is looking for an Assistant General Counsel to lead and manage external legal matters and provide strategic legal counsel as we continue to grow and evolve our consumer-finance business. This role will have primary responsibility for managing consumer litigation and arbitration, regulatory examinations and investigations, enforcement matters, and escalated legal complaints.

You will manage matters from initial assessment through resolution, including internal fact development, discovery, motion and trial strategy, settlement, and coordination with regulators and outside counsel. You will work closely with partners across Compliance, Risk, Operations, Product, Finance, and Sales to assess exposure, develop effective strategies, and communicate legal risks, trends, and insights to key stakeholders and senior leadership.

Beyond managing disputes and regulatory matters, you will also serve as a strategic legal partner to leaders across the organization as Koalafi evaluates and launches new products, capabilities, and business initiatives. You will help identify and assess legal and regulatory risks, evaluate potential exposure and tradeoffs, and provide practical, risk-based guidance that enables the business to make informed decisions and move initiatives forward. This work will span both Koalafi's traditional lending and Lease-to-Own product segments and may involve novel or evolving legal issues where sound judgment is as important as clear precedent.

This role is ideal for an attorney who combines meaningful consumer-financial-services litigation and regulatory experience with strong business judgment, practical risk assessment, and an execution-oriented mindset. You will serve as a trusted advisor to the General Counsel & Chief Compliance Officer, senior leadership, and business partners while helping Koalafi manage legal risk, support strategic growth, and build scalable processes for managing external legal matters.

Litigation, Arbitration & Dispute Resolution

• Lead Koalafi's strategy and response across individual and class-action litigation, arbitration, threatened claims, demand letters, subpoenas, and other adversarial matters.
• Manage matters throughout their full lifecycle, including initial assessment, internal fact investigation, discovery, motion practice, settlement strategy, trial preparation, and resolution.
• Assess legal, financial, operational, customer, and reputational exposure and provide clear recommendations to senior leadership.
• Direct and manage outside counsel, including matter strategy, staffing, budgets, performance, and work-product quality.
• Maintain clear reporting on active matters, significant developments, potential exposure, and emerging trends.

Regulatory Examinations & Escalated Legal Complaints

• Support Koalafi's response to regulatory examinations, investigations, inquiries, enforcement actions, and requests for information.
• Manage regulatory matters from initial request through investigation, response, remediation, settlement, or other resolution.
• Develop response strategies in partnership with the General Counsel & Chief Compliance Officer, Legal Operations team, outside counsel, and relevant internal stakeholders.
• Serve as a legal point of contact for federal and state regulators and represent Koalafi with credibility, responsiveness, and sound judgment.
• Identify patterns across regulatory matters and escalated legal complaints and communicate relevant risks to the appropriate business owners.

Legal Strategy & Operational Effectiveness

• Serve as a trusted legal advisor to the General Counsel & Chief Compliance Officer and senior leaders on strategic business initiatives, new products, and evolving operational priorities.
• Partner closely with Compliance, Risk, Operations, Product, and Sales to identify, assess, and address legal and regulatory risks associated with new and existing business initiatives.
• Translate complex or evolving legal requirements into concise, practical, risk-based recommendations that enable informed business decision-making.
• Evaluate legal risk, potential exposure, and competing business considerations to help stakeholders understand available options, tradeoffs, and paths forward.
• Provide legal guidance throughout the lifecycle of strategic initiatives, from early-stage concept and design through implementation, launch, and ongoing operation.
• Lead or support cross-functional legal workstreams on high-priority initiatives by aligning stakeholders, clarifying legal requirements, and helping drive issues toward practical resolution.
• Develop practical frameworks, playbooks, and scalable legal processes that improve consistency, speed, and quality of legal decision-making across the organization.

About You:

• Juris Doctor from an accredited law school.
• Active license to practice law in good standing in at least one U.S. jurisdiction, with the ability to practice as in-house counsel in Virginia and/or the District of Columbia.
• 8+ years of relevant legal experience at a law firm, financial institution, fintech company, regulatory agency, in-house legal department, or a combination of these environments.
• Experience in a fintech, high-growth lending, or other dynamic and highly regulated environment.
• Experience with at least one of the following: lease-to-own products, point-of-sale financing, non-prime lending, bank-partnership models, or consumer-loan servicing.
• Significant experience managing complex litigation, arbitration, regulatory investigations, enforcement matters, or other adversarial proceedings.
• Demonstrated experience advising business leaders on new products, strategic initiatives, or operational changes, including identifying legal and regulatory risks and translating them into practical, business-oriented recommendations.
• Strong knowledge of federal and state consumer-financial-services laws and regulations, including laws applicable to lending, servicing, payments, credit reporting, collections, and lease-to-own products.
• Ability to assess legal risk in areas where the law or regulatory expectations may be evolving, incomplete, or subject to interpretation, and to provide clear recommendations on options, tradeoffs, and paths forward.
• Strong advocacy, analytical, negotiation, collaboration, and communication skills, including the ability to give senior leaders concise, actionable, and risk-based advice.
• Sound judgment and the ability to independently manage multiple high-stakes matters while also partnering effectively with cross-functional teams on strategic business priorities.
• A practical, proactive, and intellectually curious approach, with a strong execution mindset and an ability to operate effectively in a fast-moving environment.

Nice to Have:

• Direct experience with the CFPB, FTC, state attorneys general, state financial-services regulators, or similar agencies.
• Capital Markets experience.

Location: Richmond, VA; Arlington, VA; or Remote (U.S.). Associates near one of our office locations may work in-office, hybrid, or remotely. Remote opportunities are available to candidates throughout the United States.

Salary Range: $180,000-$235,000 per year (depending on experience and location)

Additional Compensation: This position will be eligible to participate in company bonus plan.

The final salary offer will depend on factors including, but not limited to, experience, skills, and geographic location. The actual annualized salary amount offered to any candidate at the time of hire will be reflected solely in the candidate's offer letter.

Applications will be accepted until position is filled.

Why choose Koalafi: A career at Koalafi means opportunities to tackle exciting challenges every single day. We take pride in a culture of innovation, trust, and ownership. You'll get outside your comfort zone, build meaningful relationships, and most of all, take charge of projects that ultimately help people get the things they need most.

Benefits:

At Koalafi, you will have a direct impact on our products and help shape the company's success. We offer competitive compensation & benefits packages to keep you at your best:

• Comprehensive medical, dental, and vision coverage
• 20 PTO days + 11 paid holidays
• 401(k) retirement with company matching
• Student Loan & Tuition Reimbursement
• Commuter assistance
• Parental leave (maternal + paternal)
• Inclusion and Associate Engagement Programs

Who we are & what we value:

• We focus on what's most important
• We set clear expectations and deliver
• We embrace challenges to reach our full potential
• We ask, "How can this be better?"
• We move fast together