Open position in all True Media office locations, including Columbia, MO, St. Louis, MO, and Minneapolis, MN; Hybrid work schedule: 3 days in the office, 2 days working from home

Visa Sponsorship is not available for this position, now or in the future. Applicants must be legally authorized to work in the United States on a permanent basis without requiring employer sponsorship.

The Account Manager is responsible for managing the day-to-day execution of agency and client projects across an assigned portfolio of clients. Working under the direction of senior team members, you will maintain a clear understanding of each client’s business, marketing initiatives, and competitive landscape to oversee all details related to plan development and execution. You will serve as the primary daily client contact and be accountable for the quality, accuracy, and storytelling strength of all client-facing work.

Essential Duties and Responsibilities. (Other duties may be assigned)

• Client Communication: Serve as the day-to-day client contact; lead meetings, create agendas, produce accurate meeting summaries, and follow up on next steps. You are expected to respond promptly to client communications, handle after-hours emergencies, and anticipate and escalate problems appropriately.
• Project & Deliverable Oversight: Author or co-author business, media, and project briefs alongside the agency team. Oversee the quality and presentation of client deliverables—such as research, measurement and channel strategies, tactical plans, QA, reporting, and buy summaries.
• Approvals & Quality Assurance: Secure written client approvals for all milestone deliverables, manage client credit applications for integrated media, and ensure all deliverables align with the agency’s quality standards and the client’s strategic objectives.
• Budget Management: Supervise the preparation of client budgets, maintain regular budget sheets, provide accurate agency budget projections, and use sound judgment when approving or escalating out-of-scope requests.
• Growth & Strategy: Identify new revenue streams and client growth opportunities, develop compelling business cases, and lead brainstorming for client initiatives. You will also conduct regular retrospectives to capture campaign learnings for future initiatives.
• Partner Agency Management: Manage engagement with TIH partner agencies, including initiating engagements, negotiating scopes, holding partners accountable, and ensuring privacy protocols for personally identifiable information are followed.
• Administrative: Maintain accurate time records in the agency's tracking system, attend relevant training and meetings, delegate tasks effectively (in accordance with the agency RACI), and foster a positive agency culture.

Qualifications - To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• 2+ years of account experience in an agency or marketing setting.
• Proficiency in Microsoft Office, industry tools, and systems. Must possess a strong understanding of marketing and media fundamentals, including media math.
• Strategic thinker, excellent problem-solver, highly detail-oriented, and capable of independently managing multiple competing deadlines with strong written and verbal communication skills.
• Ability to lead day-to-day relationships and work with management and multifunctional teams to respond to client needs
• Experience in building media plan recommendations
• Excellent follow-through and no hesitation in ensuring accountability across teams
• Web analytics platform training and certification (required within 6 months and must be maintained).
• Scrum Essentials and Agile Essentials on-demand courses (required within 6 months).
• Certified Scrum Product Owner (required within 12 months and must be maintained).

Education:

• Bachelor’s degree in advertising, marketing, communications (or equivalent experience) is preferred

Total Perks Package

• The chance to be a part of a growing company and the next success story
• Amazing opportunities for career development
• Recognition programs
• Employee referral bonus
• Hybrid work schedule; 3 days in the office, 2 days working from home
• Fun and collaborative work environment
• Casual dress code
• Insurance Coverage (medical, dental, vision, life, and disability)
• 401(k) retirement plan, with employer 4% match
• Work/life benefits, including mental health and wellbeing support
• Flexible Time Off Policy
• Paid holidays, including agency soft closing Christmas Eve-New Year's Day
• Paid leave options, including sick leave, medical leave for self and family, and parental leave

Open position in all True Media office locations, including Columbia, MO, St. Louis, MO, and Minneapolis, MN; Hybrid work schedule: 3 days in the office, 2 days working from home

Visa Sponsorship is not available for this position, now or in the future. Applicants must be legally authorized to work in the United States on a permanent basis without requiring employer sponsorship.

The Account Manager is responsible for managing the day-to-day execution of agency and client projects across an assigned portfolio of clients. Working under the direction of senior team members, you will maintain a clear understanding of each client’s business, marketing initiatives, and competitive landscape to oversee all details related to plan development and execution. You will serve as the primary daily client contact and be accountable for the quality, accuracy, and storytelling strength of all client-facing work.

Essential Duties and Responsibilities. (Other duties may be assigned)

• Client Communication: Serve as the day-to-day client contact; lead meetings, create agendas, produce accurate meeting summaries, and follow up on next steps. You are expected to respond promptly to client communications, handle after-hours emergencies, and anticipate and escalate problems appropriately.
• Project & Deliverable Oversight: Author or co-author business, media, and project briefs alongside the agency team. Oversee the quality and presentation of client deliverables—such as research, measurement and channel strategies, tactical plans, QA, reporting, and buy summaries.
• Approvals & Quality Assurance: Secure written client approvals for all milestone deliverables, manage client credit applications for integrated media, and ensure all deliverables align with the agency’s quality standards and the client’s strategic objectives.
• Budget Management: Supervise the preparation of client budgets, maintain regular budget sheets, provide accurate agency budget projections, and use sound judgment when approving or escalating out-of-scope requests.
• Growth & Strategy: Identify new revenue streams and client growth opportunities, develop compelling business cases, and lead brainstorming for client initiatives. You will also conduct regular retrospectives to capture campaign learnings for future initiatives.
• Partner Agency Management: Manage engagement with TIH partner agencies, including initiating engagements, negotiating scopes, holding partners accountable, and ensuring privacy protocols for personally identifiable information are followed.
• Administrative: Maintain accurate time records in the agency's tracking system, attend relevant training and meetings, delegate tasks effectively (in accordance with the agency RACI), and foster a positive agency culture.

Qualifications - To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• 2+ years of account experience in an agency or marketing setting.
• Proficiency in Microsoft Office, industry tools, and systems. Must possess a strong understanding of marketing and media fundamentals, including media math.
• Strategic thinker, excellent problem-solver, highly detail-oriented, and capable of independently managing multiple competing deadlines with strong written and verbal communication skills.
• Ability to lead day-to-day relationships and work with management and multifunctional teams to respond to client needs
• Experience in building media plan recommendations
• Excellent follow-through and no hesitation in ensuring accountability across teams
• Web analytics platform training and certification (required within 6 months and must be maintained).
• Scrum Essentials and Agile Essentials on-demand courses (required within 6 months).
• Certified Scrum Product Owner (required within 12 months and must be maintained).

Education:

• Bachelor’s degree in advertising, marketing, communications (or equivalent experience) is preferred

Total Perks Package

• The chance to be a part of a growing company and the next success story
• Amazing opportunities for career development
• Recognition programs
• Employee referral bonus
• Hybrid work schedule; 3 days in the office, 2 days working from home
• Fun and collaborative work environment
• Casual dress code
• Insurance Coverage (medical, dental, vision, life, and disability)
• 401(k) retirement plan, with employer 4% match
• Work/life benefits, including mental health and wellbeing support
• Flexible Time Off Policy
• Paid holidays, including agency soft closing Christmas Eve-New Year's Day
• Paid leave options, including sick leave, medical leave for self and family, and parental leave

Open position in all True Media office locations, including Kansas City, MO, Columbia, MO, St. Louis, MO, Portsmouth, NH, and Minneapolis, MN; Hybrid work schedule: 3 days in the office, 2 days working from home

Visa Sponsorship is not available for this position, now or in the future. Applicants must be legally authorized to work in the United States on a permanent basis without requiring employer sponsorship.

The Account Supervisor leads the day-to-day execution of agency and client projects for an assigned portfolio. Under the guidance of senior account leadership, they maintain a comprehensive understanding of the client’s business, marketing initiatives, and competitive landscape to oversee plan development and execution. This role requires a take-charge, diplomatic leader who builds robust client relationships, fosters a collaborative team environment, and proactively drives organic revenue opportunities.

Supervisory Responsibilities This position may directly supervise employees, carrying out responsibilities such as interviewing, hiring, and training; planning, assigning, and directing work; and appraising performance, rewarding, and disciplining employees. They also communicate with the supervisors of indirect reports to manage cross-team workloads and address any complaints or problems.

Essential Duties and Responsibilities. (Other duties may be assigned)

• Identifies new revenue streams and other client growth opportunities. Is able to clearly articulate the opportunity and a strong business case POV to sell it in. 
• Review any opportunities provided by the Account Manager or Assistant Account Manager. Put the opportunity into action by attaching a next step and expertly moving the opportunity forward.
• Maintain current and accurate time records related to all functions of agency and client work assignments in the Advantage software system.
• Attends internal training, online conferences, seminars, and travels to client locations when needed.
• Actively seeks out growth and learning opportunities.
• Preserves and fosters the agency’s culture and maintains a positive and forward-thinking attitude.
• Delegates effectively and smartly, while respecting agency RACI and processes/procedures.

Qualifications - To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• 5+ years of account management experience in an agency or marketing setting, including experience managing or mentoring others.
• Proficiency with Microsoft Office, industry tools, systems, and a strong command of media fundamentals, including media math and analytics.
• Advanced strategic direction, risk management across client portfolios, strong coaching abilities, excellent communication skills, and the capacity to manage competing priorities in a fast-paced environment.
• Web analytics platform training and certification (required within six months).
• Scrum Essentials and Agile Essentials on-demand courses (required within six months).
• Certified Scrum Product Owner (required within twelve months).

Education:

• Bachelor’s degree from a four-year college or university (preferably with a concentration in advertising, marketing, or communications) or an equivalent combination of education and experience

Total Perks Package

• The chance to be a part of a growing company and the next success story
• Amazing opportunities for career development
• Recognition programs
• Employee referral bonus
• Hybrid work schedule; 3 days in the office, 2 days working from home
• Fun and collaborative work environment
• Casual dress code
• Insurance Coverage (medical, dental, vision, life, and disability)
• 401(k) retirement plan, with employer 4% match
• Work/life benefits, including mental health and wellbeing support
• Flexible Time Off Policy
• Paid holidays, including agency soft closing Christmas Eve-New Year's Day
• Paid leave options, including sick leave, medical leave for self and family, and parental leave

Open position in all True Media office locations, including Kansas City, MO, Columbia, MO, St. Louis, MO, Portsmouth, NH, and Minneapolis, MN; Hybrid work schedule: 3 days in the office, 2 days working from home

Visa Sponsorship is not available for this position, now or in the future. Applicants must be legally authorized to work in the United States on a permanent basis without requiring employer sponsorship.

The Account Supervisor leads the day-to-day execution of agency and client projects for an assigned portfolio. Under the guidance of senior account leadership, they maintain a comprehensive understanding of the client’s business, marketing initiatives, and competitive landscape to oversee plan development and execution. This role requires a take-charge, diplomatic leader who builds robust client relationships, fosters a collaborative team environment, and proactively drives organic revenue opportunities.

Supervisory Responsibilities This position may directly supervise employees, carrying out responsibilities such as interviewing, hiring, and training; planning, assigning, and directing work; and appraising performance, rewarding, and disciplining employees. They also communicate with the supervisors of indirect reports to manage cross-team workloads and address any complaints or problems.

Essential Duties and Responsibilities. (Other duties may be assigned)

• Identifies new revenue streams and other client growth opportunities. Is able to clearly articulate the opportunity and a strong business case POV to sell it in. 
• Review any opportunities provided by the Account Manager or Assistant Account Manager. Put the opportunity into action by attaching a next step and expertly moving the opportunity forward.
• Maintain current and accurate time records related to all functions of agency and client work assignments in the Advantage software system.
• Attends internal training, online conferences, seminars, and travels to client locations when needed.
• Actively seeks out growth and learning opportunities.
• Preserves and fosters the agency’s culture and maintains a positive and forward-thinking attitude.
• Delegates effectively and smartly, while respecting agency RACI and processes/procedures.

Qualifications - To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• 5+ years of account management experience in an agency or marketing setting, including experience managing or mentoring others.
• Proficiency with Microsoft Office, industry tools, systems, and a strong command of media fundamentals, including media math and analytics.
• Advanced strategic direction, risk management across client portfolios, strong coaching abilities, excellent communication skills, and the capacity to manage competing priorities in a fast-paced environment.
• Web analytics platform training and certification (required within six months).
• Scrum Essentials and Agile Essentials on-demand courses (required within six months).
• Certified Scrum Product Owner (required within twelve months).

Education:

• Bachelor’s degree from a four-year college or university (preferably with a concentration in advertising, marketing, or communications) or an equivalent combination of education and experience

Total Perks Package

• The chance to be a part of a growing company and the next success story
• Amazing opportunities for career development
• Recognition programs
• Employee referral bonus
• Hybrid work schedule; 3 days in the office, 2 days working from home
• Fun and collaborative work environment
• Casual dress code
• Insurance Coverage (medical, dental, vision, life, and disability)
• 401(k) retirement plan, with employer 4% match
• Work/life benefits, including mental health and wellbeing support
• Flexible Time Off Policy
• Paid holidays, including agency soft closing Christmas Eve-New Year's Day
• Paid leave options, including sick leave, medical leave for self and family, and parental leave

Open position in all True Media office locations, including Kansas City, MO, Columbia, MO, St. Louis, MO, Portsmouth, NH, and Minneapolis, MN; Hybrid work schedule: 3 days in the office, 2 days working from home

Visa Sponsorship is not available for this position, now or in the future. Applicants must be legally authorized to work in the United States on a permanent basis without requiring employer sponsorship.

The Account Supervisor leads the day-to-day execution of agency and client projects for an assigned portfolio. Under the guidance of senior account leadership, they maintain a comprehensive understanding of the client’s business, marketing initiatives, and competitive landscape to oversee plan development and execution. This role requires a take-charge, diplomatic leader who builds robust client relationships, fosters a collaborative team environment, and proactively drives organic revenue opportunities.

Supervisory Responsibilities This position may directly supervise employees, carrying out responsibilities such as interviewing, hiring, and training; planning, assigning, and directing work; and appraising performance, rewarding, and disciplining employees. They also communicate with the supervisors of indirect reports to manage cross-team workloads and address any complaints or problems.

Essential Duties and Responsibilities. (Other duties may be assigned)

• Identifies new revenue streams and other client growth opportunities. Is able to clearly articulate the opportunity and a strong business case POV to sell it in. 
• Review any opportunities provided by the Account Manager or Assistant Account Manager. Put the opportunity into action by attaching a next step and expertly moving the opportunity forward.
• Maintain current and accurate time records related to all functions of agency and client work assignments in the Advantage software system.
• Attends internal training, online conferences, seminars, and travels to client locations when needed.
• Actively seeks out growth and learning opportunities.
• Preserves and fosters the agency’s culture and maintains a positive and forward-thinking attitude.
• Delegates effectively and smartly, while respecting agency RACI and processes/procedures.

Qualifications - To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• 5+ years of account management experience in an agency or marketing setting, including experience managing or mentoring others.
• Proficiency with Microsoft Office, industry tools, systems, and a strong command of media fundamentals, including media math and analytics.
• Advanced strategic direction, risk management across client portfolios, strong coaching abilities, excellent communication skills, and the capacity to manage competing priorities in a fast-paced environment.
• Web analytics platform training and certification (required within six months).
• Scrum Essentials and Agile Essentials on-demand courses (required within six months).
• Certified Scrum Product Owner (required within twelve months).

Education:

• Bachelor’s degree from a four-year college or university (preferably with a concentration in advertising, marketing, or communications) or an equivalent combination of education and experience

Total Perks Package

• The chance to be a part of a growing company and the next success story
• Amazing opportunities for career development
• Recognition programs
• Employee referral bonus
• Hybrid work schedule; 3 days in the office, 2 days working from home
• Fun and collaborative work environment
• Casual dress code
• Insurance Coverage (medical, dental, vision, life, and disability)
• 401(k) retirement plan, with employer 4% match
• Work/life benefits, including mental health and wellbeing support
• Flexible Time Off Policy
• Paid holidays, including agency soft closing Christmas Eve-New Year's Day
• Paid leave options, including sick leave, medical leave for self and family, and parental leave

Open position in all True Media office locations, including Kansas City, MO, Columbia, MO, St. Louis, MO, Portsmouth, NH, and Minneapolis, MN; Hybrid work schedule: 3 days in the office, 2 days working from home

Visa Sponsorship is not available for this position, now or in the future. Applicants must be legally authorized to work in the United States on a permanent basis without requiring employer sponsorship.

The Account Supervisor leads the day-to-day execution of agency and client projects for an assigned portfolio. Under the guidance of senior account leadership, they maintain a comprehensive understanding of the client’s business, marketing initiatives, and competitive landscape to oversee plan development and execution. This role requires a take-charge, diplomatic leader who builds robust client relationships, fosters a collaborative team environment, and proactively drives organic revenue opportunities.

Supervisory Responsibilities This position may directly supervise employees, carrying out responsibilities such as interviewing, hiring, and training; planning, assigning, and directing work; and appraising performance, rewarding, and disciplining employees. They also communicate with the supervisors of indirect reports to manage cross-team workloads and address any complaints or problems.

Essential Duties and Responsibilities. (Other duties may be assigned)

• Identifies new revenue streams and other client growth opportunities. Is able to clearly articulate the opportunity and a strong business case POV to sell it in. 
• Review any opportunities provided by the Account Manager or Assistant Account Manager. Put the opportunity into action by attaching a next step and expertly moving the opportunity forward.
• Maintain current and accurate time records related to all functions of agency and client work assignments in the Advantage software system.
• Attends internal training, online conferences, seminars, and travels to client locations when needed.
• Actively seeks out growth and learning opportunities.
• Preserves and fosters the agency’s culture and maintains a positive and forward-thinking attitude.
• Delegates effectively and smartly, while respecting agency RACI and processes/procedures.

Qualifications - To perform this job successfully, an individual must be able to perform each essential duty satisfactorily. The requirements listed below are representative of the knowledge, skill, and/or ability required. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.

• 5+ years of account management experience in an agency or marketing setting, including experience managing or mentoring others.
• Proficiency with Microsoft Office, industry tools, systems, and a strong command of media fundamentals, including media math and analytics.
• Advanced strategic direction, risk management across client portfolios, strong coaching abilities, excellent communication skills, and the capacity to manage competing priorities in a fast-paced environment.
• Web analytics platform training and certification (required within six months).
• Scrum Essentials and Agile Essentials on-demand courses (required within six months).
• Certified Scrum Product Owner (required within twelve months).

Education:

• Bachelor’s degree from a four-year college or university (preferably with a concentration in advertising, marketing, or communications) or an equivalent combination of education and experience

Total Perks Package

• The chance to be a part of a growing company and the next success story
• Amazing opportunities for career development
• Recognition programs
• Employee referral bonus
• Hybrid work schedule; 3 days in the office, 2 days working from home
• Fun and collaborative work environment
• Casual dress code
• Insurance Coverage (medical, dental, vision, life, and disability)
• 401(k) retirement plan, with employer 4% match
• Work/life benefits, including mental health and wellbeing support
• Flexible Time Off Policy
• Paid holidays, including agency soft closing Christmas Eve-New Year's Day
• Paid leave options, including sick leave, medical leave for self and family, and parental leave

Our Company

Established in 2016 and headquartered in Minneapolis, Minnesota, Sezzle Inc. is a publicly traded financial technology company (Nasdaq: SEZL) operating in the United States and Canada. With a mission to financially empower the next generation, Sezzle is revolutionizing the shopping experience beyond payments, blending cutting-edge tech with seamless, interest-free installment plans that make shopping smarter and more accessible. We’re not just transforming payments; we’re redefining how people discover, interact with, and purchase the things they love while driving real impact on merchant sales through increased conversions and higher order values. Sezzle currently employs approximately 400 employees and contractors, with gross annual revenue exceeding $450 million and net income of more than $133 million (based on our 2025 Annual Report).

The Position

We are seeking a best in class tech-driven General Counsel. This role presents an exciting opportunity to thrive in a dynamic, fast-paced environment within a rapidly growing team.

The General Counsel serves as Sezzle’s most senior legal and compliance executive, providing strategic legal leadership across all business lines while directly overseeing the Compliance department. This is not a traditional legal role. We are a technology company first, and our GC must lead with that same orientation, embracing AI-powered legal operations, accelerating the team’s use of emerging tools, and acting as a force multiplier for Sezzle’s speed of innovation. The GC will own the full legal and compliance mandate including consumer lending regulation, state and federal licensing, ILC bank charter regulatory strategy, corporate governance, product counsel, and enterprise risk.

This role is critical to Sezzle’s next chapter. As we pursue a Utah Industrial Loan Company (ILC) bank charter and build out a full-service consumer financial platform, the GC will be at the center of some of the most consequential legal and regulatory decisions in the company’s history.

What You’ll Do

Legal Leadership

• Lead Sezzle’s legal function as a technology-first operator, not a traditional counsel. You will be expected to actively implement and champion AI tools across the legal and compliance team, from contract review and regulatory research to compliance monitoring and risk analysis, setting the standard for how a modern in-house legal department operates. This is not aspirational; it is a baseline expectation from day one.
• Serve as the company’s primary legal advisor to the CEO, executive team, and Board on all legal, regulatory, and strategic matters.
• Lead, manage, and build Sezzle’s in-house legal team, setting a high-performance culture consistent with Sezzle’s Merit, Excellence, and Intelligence values.
• Oversee all corporate governance matters including Board minutes, charter documents, equity management, securities compliance, and public company obligations.
• Manage litigation, outside counsel relationships, and legal spend with a results-driven, efficiency-first orientation.
• Provide real-time legal guidance on product development, marketing, technology partnerships, and business strategy.
• Lead or support M&A, debt facility, and strategic transaction work as Sezzle’s business evolves.

Compliance & Regulatory Leadership

• Directly lead and own Sezzle’s Compliance department, overseeing the team, program structure, and regulatory posture across the U.S. and Canada.
• Own all consumer lending regulatory compliance including TILA/Reg Z, ECOA, FCRA, UDAAP, GLBA, CCPA/GDPR, and state-level consumer protection laws.
• Lead state licensing strategy including money transmission, consumer finance, and lending licenses across all active jurisdictions.
• Act as primary point of contact for CFPB, FTC, state banking regulators, and other relevant regulatory bodies.
• Own Sezzle’s ILC bank charter regulatory strategy in partnership with the CEO and executive team, guiding application, charter management, ongoing regulatory relationships, and bank-level compliance build-out.
• Develop and maintain enterprise-wide compliance programs, policies, and training frameworks.
• Lead regulatory examination and audit preparation, response, and resolution.

AI & Technology Transformation

• Champion the adoption and implementation of AI tools within the Legal and Compliance departments, drafting, research, contract review, regulatory monitoring, and compliance automation.
• Actively partner with Engineering and Product on AI-powered product initiatives, ensuring legal and compliance are accelerators rather than gatekeepers.
• Set and model a culture where legal team members are expected to leverage AI in their daily practice.
• Advise on legal risk associated with Sezzle’s proprietary AI development, including the AI shopping assistant, algorithmic credit decisioning, and data strategy.

What We Look For

• Demonstrated track record of leading AI implementation within a legal or compliance function, not as an observer but as an owner and driver of adoption.
• Experience building or leading compliance operations at a high-growth fintech, digital lender, or regulated technology company.
• Regulatory experience navigating CFPB, FTC, state banking regulators, and/or FDIC examinations.
• Exceptional ability to translate complex regulatory requirements into clear, actionable business guidance without slowing execution.
• Strong team-building instincts, this person leads a department and sets the culture for how legal and compliance operates at Sezzle.
• Strategic thinker with operational discipline, can set direction and execute.
• Excellent written and verbal communication skills; comfortable presenting to the Board and external regulators.
• Deep expertise in U.S. consumer lending regulation with direct BNPL, pay-in-four, short-term lending, earned wage access, or adjacent consumer finance experience is preferred. 

Preferred Qualifications

• J.D. from a top-ranked U.S. law school; law review or equivalent academic distinction preferred.
• 8–15 years of relevant legal experience; a mix of elite law firm and in-house is the ideal trajectory.
• Direct experience with ILC charter applications or de novo bank formation is a significant differentiator.
• Prior experience in BNPL, payday lending, consumer installment lending, personal loans, or near-Sezzle consumer finance verticals strongly preferred.
• Background or active interest in financial technology product development, candidates who have coded, prototyped, or built internal legal-tech tools are of particular interest.
• Public company experience (SEC reporting, Regulation FD, proxy statements) is a plus; Sezzle is publicly traded on Nasdaq.
• Familiarity with Canadian consumer protection law is an asset.

About You

• You have relentlessly high standards; many people may think your standards are unreasonably high. You are continually raising the bar and driving those around you to deliver great results. You make sure that defects do not get sent down the line and that problems are fixed so they stay fixed.
• You’re not bound by convention; your success and much of the fun, lies in developing new ways to do things.
• You need action; speed matters in business. Many decisions and actions are reversible and do not need extensive study. We value calculated risk-taking.
• You earn trust; you listen attentively, speak candidly, and treat others respectfully.
• You have backbone; disagree, then commit. You can respectfully challenge decisions when you disagree, even when doing so is uncomfortable or exhausting. You have conviction and are tenacious. You do not compromise for the sake of social cohesion. Once a decision is determined, you commit wholly.
• You deliver results; you focus on the key inputs and deliver them with the right quality and in a timely fashion. Despite setbacks, you rise to the occasion and never settle.

What Makes Working at Sezzle Awesome

At Sezzle, we are more than just brilliant engineers, passionate data enthusiasts, out-of-the-box thinkers, and determined innovators. We believe in surrounding ourselves with only the best and the brightest individuals. Our culture is not defined by a certain set of perks designed to give the illusion of the traditional startup culture, but rather, it is the visible example living in every employee that we hire.

#Li-remote

Technical Solution Owner – Inspire11

Elevens, as we call ourselves here, are curiously smart, purposefully scrappy, and dedicated to the highest standard of quality. By being true to ourselves and others, we create a respectful environment that enhances collaboration, drives growth through high expectations, and ensures alignment with our core values. Inspire11 is more than a modern business and technology consulting firm; we're a revolution. We work differently — and it shows. Every move we make is tied to measurable value, and our success aligns with our clients’ success. We partner to simplify the complex, solve sustainably, and stay ahead by continuously pushing our own thinking forward. Value creation isn't something we talk about — it's something we live, every day. 

At Inspire11, we're not just offering a job; we're providing a platform for you to transform the future. You'll feel right at home here if you think differently, build boldly, and lead with impact. We're a place where your unique perspective is valued, your boldness is celebrated, and your potential is unleashed. 

• Growth Through Challenge:  We hold ourselves to the highest standards of excellence and accountability. At Inspire11, we are committed to delivering exceptional results and empowering our employees to take ownership of their work and drive meaningful impact. You'll work alongside elite consultants who challenge you to expand your skills and think even more creatively. 

• The Autonomy to do Your Best Work: Here, outcomes matter more than outputs. It's about the value we create. You'll have the autonomy to shape your work, drive decisions, and make an impact—not just for our clients but for your growth. You'll be challenged to think strategically, anticipate needs, and solve problems. Bold thinking, creative approaches, and challenging conventional wisdom are part of our DNA. Our clients rely on us to lead them into what's next. 

• Diverse Perspectives Driving Innovative Solutions: We champion inclusivity and authenticity, knowing that diverse perspectives drive better solutions. You'll be encouraged to bring your whole self to work, knowing that's where true innovation happens. We also believe that doing great work should be fun. Our culture thrives on energy, camaraderie, and appreciating the unique contributions that make Inspire11 an amazing place. Our teams get energy from being the best they can be. 

 What you can expect in this role: 

• Lead and deliver complex technical solutions on time and within budget, managing programs and projects end-to-end in Agile environments.
• Drive product ideation, discovery, and co-development models to bring innovative solutions to market.
• Lead scoping, solution design, and estimation of technical work and define an actionable implementation plan. 
• Architect and plan solutions leveraging modern cloud, data, and digital technologies; ensure alignment to client goals and value realization.
• Manage team performance, delivery, and growth while fostering collaboration across functional and technical resources.
• Build and maintain trusted client relationships, proactively managing expectations, risks, and opportunities.
• Deliver clear, compelling communications and performance metrics that demonstrate business value and technical excellence.
• Leverage the latest automation capabilities to drive efficiencies across discovery and development activities. 

Tools for success: 

• 5+ years of experience leading technical delivery across custom software, data, analytics, or digital transformation programs.
• Proven ability to scope, estimate, and decompose work for delivery teams; experience in technical requirements capture, capacity planning, and Agile frameworks.
• Strong program/project management skills including budget oversight, risk management, and performance reporting.
• Ability to communicate business value of complex technical solutions to business stakeholders to inspire client confidence.
• Experience with cloud services foundations (AWS, Azure, GCP) and cloud solution architecture (nice to have).
• Comfortable supporting product ideation, rapid prototyping, and co-development operating models (nice to have).
• Strong communication, client management, problem solving, and people leadership skills. 

This role requires the willingness and ability to be onsite at the Inspire11 or client location depending on project needs to maximize in-person collaboration and build stronger relationships. 

Inspire11 is unable to sponsor employment visas at this time. Applicants must be legally authorized to work in the U.S. at the time of application and throughout the duration of employment. 

Inspire11’s Privacy Policy: https://www.inspire11.com/privacy-policy/  

U.S. Compensation & Benefits  

Compensation at Inspire11 
Inspire11 follows Title VII of the Civil Rights Act of 1964, the Equal Pay Act of 1963, the Illinois Human Rights Act, the Illinois Equal Wage Act, and the Illinois Equal Pay Act of 2003. We believe that people performing the same role at the same level, with similar levels of ability or experience, should be similarly compensated. We also believe that the most critical factors driving compensation should be an Eleven’s skill, experience, performance, responsibility, and effort. We may also consider an employee’s length of service, relevant education, training, or certification, and the requirements of a specific job. We may also consider whether the cost of living or competition for talent in specific markets requires adjustments in compensation for employees in those markets. Our goal is to fairly compensate all our Elevens based on these factors within the Company’s financial ability.   

Compensation may be increased or decreased at Inspire11’s discretion based on an employee’s performance reviews, market conditions, and the Company’s financial performance. Inspire11 will always notify an employee in writing before any change is made to their compensation.  

Bonuses 
We may allow employees in Sales, Recruiting, or Leadership to earn periodic bonuses based on sales, revenue, client-specific or practice-specific targets. These targets are communicated to each eligible employee via offer letter or annual update. All such target-based bonuses are calculated based on the Company and an individual’s periodic performance and will only be awarded if: (a) the employee is meeting performance expectations and is an employee in good standing of the Company; (b) the target is met; and (c) the Company’s current financial performance and market conditions permit the bonus to be paid out. All periodic bonuses are discretionary and are earned only when paid out.   

Each year, the Company will decide whether the Company’s financial performance, market performance, and business realities allow it to create an annual bonus pool. If the Company decides that annual bonuses may be awarded, then the Leadership Team will grant annual bonuses to employees in good standing based on the same factors discussed in the previous paragraph while also considering employees’ diligence, performance, expertise, skill, judgment, and experience. To be eligible to participate in this annual bonus pool, an employee must be hired by no later than October 1st of the preceding year. Annual bonuses and merit increases may be prorated based on hire date. Employees eligible for target-based periodic bonuses are not eligible to participate in the annual bonus pool.   

Options or Other Equity in Inspire11 
Inspire11 has a legacy program that allowed certain high-performing employees to purchase shares of the Company through an affiliate. The Company also has a newer program that grants options annually to high-performing employees based on their performance reviews, their managers’ recommendation, and leadership approval. These options have a vesting period associated with them.  

Benefits 
Full-time employees are eligible for the following contributory benefits, where premiums are partially paid by the Company and partially by the employee:   

• Medical insurance plans, 
• Dental insurance plans, and  
• Vision insurance plans.  

Full-time employees are eligible for the following benefits provided wholly by the Company:  

• Short-term disability, providing for a benefit of 60% of an employee’s salary up to a maximum of $2,000 per week for up to 11 weeks after a 7-day waiting period; 
• Long-term disability, providing for 60% of an employee’s salary up to a maximum of $10,000 per month for the time period from the 91st day after a qualifying event through the earlier of the end of the disability or age 67; 
• Life insurance, providing for a benefit of two times the employee’s annual salary, up to a maximum payout of $400,000;   
• A connectivity stipend of $325 annually; 
• Employee Assistance Program, providing for confidential counseling sessions, 24-hour crisis support, online peer support groups, skills training, behavioral health coaching, initial free legal consultations (and discounted rates on referred lawyers), online legal forms, assistance with eldercare and parenting services, among other things.  

Full-time employees are also eligible to participate in the Company’s 401(k) plan, which allows employees to contribute to a standard or Roth IRA. According to a vesting schedule, the Company matches 100% of employee contributions up to 3% of an employee’s salary.  

Depending on eligibility and their elections, full-time employees may also have access to certain tax-advantaged savings accounts set up through the Company, into which employees contribute withheld funds:   

• Flexible savings accounts
• Limited-purpose flexible savings accounts  
• Healthcare savings accounts
• Dependent care savings accounts  
• Commuter benefit accounts  

Paid Time Off and Leave 
Inspire11 grants all eligible employees any statutory leave required by federal, Illinois, or other applicable law, such as FMLA, bereavement, sick leave, emergency leave, jury duty or witness leave, and VESSA leave.   

In addition, Inspire11 has a self-managed paid time off policy (PTO) that does not set predetermined upper limits on the amount of PTO an employee may take. All PTO must be requested in advance and approved by the appropriate supervisor to ensure client work can continue. All full-time employees are expected to take a minimum of one week of PTO each year.   

Inspire11 offers paid parental leave to full-time employees who have been with the company for at least one year. Birthing parents are eligible for up to 12 weeks of paid parental leave, while non-birthing parents are eligible for up to 6 weeks. Short-term disability (STD) benefits are also provided following childbirth. When combined with PTO and STD, birthing parents may receive a total of 18–20 weeks of paid leave. Lastly, Inspire11 has eight paid holidays.  

Other Benefits 
Inspire11 also maintains other programs that provide additional benefits to employees, such as:   

• Impact to 11: a charitable giving matching program where, after being employed by Inspire11 for a year, employees may request that a qualifying charity receive up to $500 in matching donations each year. 
• Professional development benefits for qualifying employees: a program allowing for reimbursement of certain course materials and costs on a discretionary basis for employees who have been at Inspire11 for at least 6 months, with supervisor’s approval. 
• Regular gifts of Inspire11 clothes, office items, and swag.  

Disclaimer 
This document applies only to the United States and to Inspire11 LLC, not our worldwide partners.  

Inspire11 reserves the right to change the benefits offered to employees in accordance with applicable law based on business needs, market conditions, and financial stability. Before changing any benefits, Company will notify all employees of the change and will update this document.  

EEOC 
Inspire11 is an Equal Opportunity Workplace and an Affirmative Action Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability, or protected veteran status. If you need assistance or a reasonable accommodation during the application process, please contact us at hr@inspire11.com, or inform your recruiting partner.