Sezzle Inc.

UNITED STATES

SECURITIES AND EXCHANGE COMMISSION

Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of the

Securities Exchange Act of 1934

(Amendment No. )

Check the appropriate box:

SEZZLE INC.

(Name of Registrant as Specified in Its Charter)

Not applicable.

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

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Letter from our Executive Chairman and Chief Executive Officer

Dear Fellow Shareholders,

We started this journey with a simple belief: consumers deserved a better way to pay, one that was flexible, responsible, and aligned with their financial lives. What we did not fully appreciate at the outset was how much that belief could compound. Not only in revenue, subscribers, or net income, but in what it would teach us about building a business meant to endure.

2025 marked our tenth year. It was also, in many ways, our most instructive.

Over the past decade, we have learned that durable businesses are not built on momentum alone. They are built on feedback loops: testing, learning, refining, and compounding. In 2025, that lesson became especially clear.

Proving the Model, Sharpening the Focus

2025 marked the first full year of operating under our bank sponsorship model. That model helped us unify our product nationally, unlocked the ability to launch On-Demand, and expanded the ways we can serve consumers in their everyday financial lives. This foundation matters not only for what it enabled in 2025, but for what it makes possible in the years ahead.

On-Demand was one of the most important product tests that followed. We launched it with a mission to lower the barrier to entry for new consumers, strengthen our position with enterprise merchants, and create a broader entry point into the Sezzle ecosystem.

Just as important as launching the product was how we evaluated it. We invested in On-Demand, studied the data closely, and let the lifetime value profile guide our decisions. By mid-year, the data made the path forward clear and reinforced what we had believed for some time: there is a meaningful difference between a consumer who uses Sezzle when it appears at checkout and one who has made Sezzle their default option through subscription. The first is a transaction. The second is a relationship. Our subscription model is designed to deepen that relationship and make Sezzle a top-of-wallet choice.

That experience reflects a core principle of how we operate this business. We are willing to test, invest, learn, and pivot when the facts warrant it. In this case, the result was a stronger conviction about where we believe the highest lifetime value resides and the greatest return on investment lies. We shifted our focus back toward subscription growth, while retaining On-Demand as an option for consumers for whom a subscription is not the right fit. From a low of 481,000 subscribers in the first quarter, we grew to nearly 670,000 by year-end, representing a nearly 40% increase. And On-Demand users grew at a similar pace over the same period. The pivot did not come at the expense of total engagement. It deepened it.

Building the Everyday App

In 2025, consumer engagement deepened well beyond the checkout button. Shoppers who came to Sezzle for payments increasingly engaged with our Earn Tab, Product Marketplace, Price Comparison tool, Browser Extension, and other features that added value beyond checkout. Each layer strengthened engagement, and the engagement compounded over time.

The impact is clear. Monthly app sessions grew 51% year-over-year in December, and our Earn Tab is generating approximately $1 million in monthly revenue. Together, these results reinforce a broader point: consumers want more from Sezzle than just a checkout button.

That engagement laid the groundwork for the next phase of our evolution. In 2026, we moved beyond our Pay-in-4 roots in checkout with Pay-in-5, Sezzle Mobile, SezzleCash, and Sezzle Send. SezzleCash gives eligible subscribers access to short-term liquidity, while Sezzle Send brings peer-to-peer payments into the Sezzle ecosystem. Together, these products give consumers more reasons to engage with Sezzle and move us closer to our vision of building an all-in-one financial platform.

Underpinning all of this is AI. We consume it across the business, but what makes us different is that we are also building it. Proprietary systems, embedded underwriting models, internal data tooling, and automation enable our Sezzlers to do more than ever before. That combination is what allows our lean team to operate above its weight, and helps bridge the gap between what consumers are asking for and how fast we can deliver it.

Scaling with Discipline

The combination of deeper consumer relationships and stronger operational leverage is what ultimately drives the financial performance we are proud to share.

In 2025, we delivered $133.1 million in net income, a 70% increase year-over-year, and generated $209.9 million in cash from operations. That financial strength gives us the flexibility to invest in growth while also returning capital to shareholders. In 2025 we executed a 6-for-1 stock split, completed our $50 million share repurchase program, and announced a new $100 million share repurchase authorization. These actions reflect our strategy for a durable cash-generating business and our commitment to long-term shareholder value.

That momentum has carried into 2026. Since initially setting our outlook for the year, we have raised our financial guidance multiple times as the core business has continued to outperform our expectations. Importantly, this outlook reflects the strength of our existing business and does not include the contribution from SezzleCash and Sezzle Send, which we recently launched. A strong foundation is in place, and we are building for the upside.

What We Are Building Toward

The first ten years were about proving the model: that this business could be profitable, disciplined, and aligned with the consumers it serves. Our focus over the next ten years is deepening that relationship and expanding how we support our consumers every day.

Supporting that ambition also means continuing to strengthen the infrastructure beneath our platform. With this goal in mind, we are pursuing a national bank charter, an important step in our long-term strategy to create a more durable and scalable foundation for Sezzle. Subject to regulatory approval, we believe a national bank charter can provide flexibility as we expand our product suite, deepen our consumer relationships, and continue building for the long term.

Our confidence in that next chapter comes from what we have already built: a platform with a devoted consumer base engaging well beyond payments, a business model that is designed to generate enough cash to fund its own growth while returning capital to shareholders, and a team that knows how to pivot and move fast without losing discipline. That combination is rare, and we do not take it for granted.

None of what we accomplished in 2025 happened by accident. It happened because of the Sezzlers who show up every day with the talent, drive, and belief in what we are building. I want to thank every one of them.

To you, our shareholders, and especially those who have been with us since the early days: thank you for the trust you placed in us long before the results were visible. A decade in, we are still building with the same hunger with which we started. That passion is never going to change.

Sincerely,

Charles Youakim

Executive Chairman and Chief Executive Officer

NOTICE OF THE 2026 ANNUAL MEETING OF STOCKHOLDERS

TO BE HELD ON

THURSDAY, NOVEMBER 19, 2026 AT 2:00 PM (U.S. EASTERN TIME)

TO THE STOCKHOLDERS OF SEZZLE INC.:

Please take notice that the Annual Meeting of Stockholders (the “Annual Meeting”) of Sezzle Inc. (the “Company”) will be held on Thursday, November 19, 2026 at 2:00 PM (US Eastern Time), via virtual meeting conducted exclusively online via live webcast at meetnow.global/M5GSLDV, for the following purposes, as more fully described in the accompanying proxy statement (the “Proxy Statement”):

1. The election of five directors named in the Proxy Statement to serve until the next annual election and their successors are duly elected and qualified;

2. The ratification of the Audit & Risk Committee's selection of PricewaterhouseCoopers LLP as our independent registered public accounting firm for the fiscal year ending December 31, 2026;

3. The advisory vote to approve executive compensation; and

4. The transaction of any other business as may properly come before the Annual Meeting or any postponements or adjournments thereof.

Pursuant to due action of the Board of Directors, stockholders of record on Tuesday, September 29, 2026 at 5:00 p.m. (US Eastern Time) will be entitled to vote at the Annual Meeting or any postponements or adjournments thereof.

This Notice is accompanied by a Proxy Statement, a Proxy Form, and Voting Instructions Form, which all form part of this Notice.

The Proxy Statement and the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2025 are also available to you on the Internet. To view the proxy materials on the Internet, visit investors.sezzle.com.

These proxy materials are being made available or distributed to you on or about October 9, 2026. We encourage you to review all of the important information contained in the proxy materials before voting.

By Order of the Board of Directors

Charles Youakim

Executive Chairman and Chief Executive Officer

Minneapolis, Minnesota

October 9, 2026

PROXY STATEMENT FOR THE 2026 ANNUAL MEETING OF STOCKHOLDERS

TO BE HELD ON NOVEMBER 19, 2026 AT 2:00 PM (U.S. EASTERN TIME)

IMPORTANT INFORMATION

Record Date

You are entitled to notice of, and to vote at, the Meeting (and any adjournment or postponement thereof) if you were a Stockholder on Tuesday, September 29, 2026 at 5:00 p.m. (US Eastern Time) (the Record Date).

Voting by Proxy

Whether or not you plan to participate in the virtual Meeting, you can ensure that your shares are represented at the Meeting by promptly completing, signing and returning the Proxy Form or voting and submitting your Proxy Form online, in each case in accordance with the instructions on the Proxy Form, as soon as possible. If you later decide to participate in the virtual Meeting, you may withdraw your proxy and vote in person via the webcast.

Electronic Copy

An electronic copy of this Notice and accompanying documents is available on the Company’s website at investors.sezzle.com.

Virtual Meeting

This year’s Annual Meeting will be conducted virtually using an online meeting platform accessible at meetnow.global/M5GSLDV. You will not be able to attend the Annual Meeting in person.

You are entitled to attend the virtual Annual Meeting only if you were a Company stockholder as of the Record Date or you hold a valid proxy for the Annual Meeting.

You must log into the online Annual Meeting platform to attend the Annual Meeting. By attending the Annual Meeting online, you will be able to:

•hear the Annual Meeting discussion and view presentation slides;

•submit written questions while the Annual Meeting is progressing; and

•vote during the Annual Meeting.

We recommend logging into the online platform, meetnow.global/M5GSLDV, at least 15 minutes prior to the scheduled start time for the Annual Meeting using the control number on your proxy card, voting instruction form or Notice of Internet Availability of Proxy Materials.

Even if you plan to attend the virtual Annual Meeting, we encourage you to vote via the Internet or by mail prior to the Annual Meeting.

Stockholders are also encouraged to submit any questions in advance of the Annual Meeting to the Company. Questions must be submitted in writing to the Company by email to investorrelations@sezzle.com at least 48 hours prior to the Annual Meeting.

Stockholders will also have the opportunity to submit written questions during the Annual Meeting in respect to the formal items of business, however it would be preferable for questions to be submitted to the Company in advance of the Meeting. In order to ask a question during the Annual Meeting, please follow the instructions from the Chairman.

Additional information regarding the rules and procedures for participating in the Annual Meeting will be provided in our meeting rules of conduct, which stockholders can view during the Annual Meeting at the meeting website.

IMPORTANT: To ensure that your shares are represented at the Annual Meeting, please vote your shares via the Internet or by marking, signing, dating and returning the enclosed proxy card or applicable voting instruction form to the address specified. If you attend the meeting, you may choose to vote online during the virtual Annual Meeting even if you have previously voted your shares, except that beneficial owners may only instruct their broker, bank or other holder of record to vote on their behalf by following the instructions on the enclosed applicable voting instruction form. Beneficial owners may not vote online at the Annual Meeting unless a valid proxy has been obtained from their broker, bank or other holder of record, as the case may be, with respect to their ownership interests.

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