Item 1.01 Entry into a Material Definitive Agreement.
On February 24, 2021, USA Technologies, Inc. (the “Company”) entered into separate subscription agreements in identical form and substance
(the “Subscription Agreements”) with institutional accredited investors (the “Purchasers”) relating to a private placement (the “Private Placement”) with respect to the sale of an aggregate of 5,730,000 shares (the “Shares”) of the Company’s common
stock, no par value (the “Common Stock”). The Company anticipates that it will receive aggregate gross proceeds from the Private Placement of $55 million, before deducting fees to the placement agents and other estimated offering expenses payable by
the Company, based on the offering price of $9.60 per share (the “Purchase Price”). The financing syndicate includes Hudson Executive Capital LP (“HEC”), the Company’s largest shareholder. HEC will purchase 975,000 of the Shares to be sold in the
Private Placement for the same Purchase Price and on the same terms as the other Purchasers. The Purchase Price and other terms of the Private Placement were approved by a special pricing committee of the Company’s board of directors comprised solely
of independent and disinterested directors. The Private Placement is expected to close on or about March 1, 2021, subject to customary closing conditions. The Company intends to use the proceeds of the Private Placement for general corporate
purposes.
The Shares to be issued in the Private Placement will be exempt from the registration requirements of the Securities Act of 1933, as amended
(the “Securities Act”) pursuant to Section 4(a)(2) of the Securities Act because, among other things, the transaction will not involve a public offering, the Purchasers are accredited investors, the Purchasers will take the Shares for investment and
not resale purposes, and the Company will take appropriate measures to restrict the transfer of the Shares. The Shares will not be registered under the Securities Act and, once issued, may not be sold in the United States absent registration or an
exemption from registration. This Current Report on Form 8-K shall not constitute an offer to sell or the solicitation of an offer to buy, nor shall there be any sale of the Shares in any state or jurisdiction in which such offer, solicitation or
sale would be unlawful prior to registration or qualification under the securities laws of any such state or jurisdiction.
The Subscription Agreements contain representations and warranties that the parties made to, and solely for the benefit of, the others in the
context of all of the terms and conditions of that agreement and in the context of the specific relationship between the parties. Pursuant to the Subscription Agreements, the Company has agreed to file a registration statement covering the resale of
the Shares within 45 days following the date of the Subscription Agreements and to cause the registration statement to become effective within 60 days following the filing deadline. If the Company fails to meet the specified deadline for the
effectiveness of the registration statement covering the resale of the Shares, the Company will be required to pay liquidated damages to the Purchasers in an amount equal to 1% of the aggregate purchase price paid by the Purchasers on each 30th day
of delinquency, subject to a maximum payment equal to 10% of the gross proceeds of the Private Placement. The provisions of the Subscription Agreements, including the representations and warranties contained therein, are not for the benefit of any
party other than the parties to such agreement and are not intended as documents for investors and the public to obtain factual information about the current state of affairs of the parties to that agreement. Investors and the public should look to
other disclosures contained in the Company’s filings with the U.S. Securities and Exchange Commission.
J.P. Morgan Securities LLC acted as lead placement agent and Craig-Hallum Capital Group LLC and Northland Capital Markets acted as joint
placement agents in connection with the Private Placement (together, the “Placement Agents”). The Company agreed to pay the Placement Agents an aggregate cash fee of approximately $2.28 million, representing 5% of the gross proceeds of the Private
Placement, excluding the gross proceeds received by the Company from HEC in the Private Placement.
The forgoing descriptions of the Subscription Agreements are not complete and are qualified in their entirety by reference to the Subscription
Agreements, the form of which is attached as Exhibit 10.1 to this Current Report on Form 8-K and incorporated herein by reference.