Risk Investigator II

WHO WE ARE
Welcome to KORT Payments, where innovation meets excellence! We specialize in providing a state-of-the-art omnichannel payments platform designed to make business transactions a breeze. Our mission? To empower businesses with top-notch capabilities in compliance, risk management, and payment processing. Our trailblazing, enterprise-grade platform, coupled with a veteran management team, ensures we stay ahead of the curve in delivering unparalleled service and satisfaction.
As we continue to grow across North America, we're excited to bring our proven solutions and innovative approach to new industries, while operating under the KORT Payments banner alongside Merrco, Payfirma and Barnet.

LOCATION Toronto

EMPLOYMENT TYPE Full-time, salaried, new role

SALARY RANGE $80,000 - $90,000
Actual compensation will be determined based on location, experience, and role requirements, and will comply with applicable local pay transparency laws.

WHAT YOU WILL BE DOING
The Risk Investigator II is an experienced individual contributor within the Risk team, responsible for complex merchant investigations and time-sensitive operational risk work across KORT's U.S. merchant portfolio. Reporting to the Director of Risk, this role combines advanced transaction and portfolio monitoring with risk-based enhanced due diligence (EDD), payment-network and sponsor-bank support, operational escalations, and clear communication with merchants and business partners. You will assess high-risk and card-not-present merchants, translate findings into practical recommendations, and partner with Credit, Compliance/AML, Operations, Collections, Reporting, and external stakeholders. Final decisions on material reserve changes, account restrictions, closures, and other high-impact actions remain with Risk leadership, while potentially unusual activity is escalated through the appropriate Compliance referral process.

Monitor transaction activity, portfolio alerts, and relevant risk reporting to identify potential fraud or misuse and material changes in chargebacks, disputes, refunds, declines, authorization behavior, transaction velocity, ticket size, or processing volume
Conduct complex merchant and partner investigations using processing history, underwriting records, websites and customer journeys, public records, adverse information, related-account linkages, and reserve or financial-exposure data
Perform or coordinate risk-based EDD and targeted merchant reviews when ownership, banking information, websites, products, business models, geography, financial condition, or processing behavior materially changes; partner with Credit when renewed underwriting is required
Investigate time-sensitive payment-network and sponsor-bank matters; organize evidence, track required deadlines, assess merchant responses, and prepare clear recommendations for remediation or escalation
Compare actual activity with the approved merchant profile, including products and services, sales channels, transaction patterns, customer geography, fulfillment practices, disclosures, and financial exposure; recommend proportionate monitoring, remediation, account controls, or escalation
Manage clear and timely communications with merchants and business partners regarding account reviews, documentation requests, funding-related questions, remediation expectations, and next steps, while escalating sensitive or high-impact decisions to management
Review complex merchant profile and account-change requests and support funding or reserve-related decisions by validating authority, documentation, account status, financial exposure, downstream refund or chargeback risk, and applicable approval requirements
Maintain accurate case notes, tickets, evidence, and follow-up dates; support retrospective risk reviews and escalate potentially unusual activity through established Compliance channels; ensure high-priority matters have a documented owner, next step, and escalation path
Identify recurring merchant, partner, system, and process gaps; develop procedures, checklists, decision tools, and reporting improvements; and provide quality assurance, cross-training, and practical guidance to less-experienced Risk staff

WHAT WE'RE LOOKING FOR

Bachelor's degree or equivalent experience in finance, risk, compliance, criminal justice, business, accounting, or a related field
4+ years of experience in merchant risk investigations, transaction monitoring, payments fraud, acquiring operations, enhanced due diligence, or a related financial-services risk function; merchant acquiring, ISO, or payment-facilitator experience is strongly preferred
Demonstrated experience assessing high-risk and card-not-present merchant models, including recurring billing, subscription services, digital commerce, direct marketing, or other complex business models, and distinguishing expected activity from meaningful risk indicators
Hands-on experience with risk-based EDD, KYB/KYC reviews, ownership and related-entity analysis, adverse-information research, merchant profile changes, and documented escalation of potentially unusual activity
Working knowledge of payment-network and sponsor-bank monitoring, reporting, remediation, and compliance requirements
Strong analytical ability across processing data, fraud, chargebacks, disputes, refunds, declines, authorizations, reserves, financial exposure, financial statements, bank documentation, websites, and other external information sources
Excellent written and verbal communication, disciplined case documentation, sound escalation judgment, and the ability to manage multiple time-sensitive investigations; knowledge of U.S. payments risk considerations is preferred

LIFE AT KORT PAYMENTS
We believe work should be fulfilling and fun! Here’s a peek into what life with us is like:
Culture:

Fearlessness: Encourage continuous learning, innovation, taking chances, and pushing boundaries
Accountability: Take ownership and be accountable to yourself, the company, partners, and clients
Collaboration: Leverage diverse perspectives and work as a team to get the job done
Transparency: Empower success through open communication, honesty, and inclusion

Perks and Benefits:

Comprehensive Benefits Package: We've got you covered with health, dental, and vision plans
Flexible and Inclusive Work Environment: We understand the importance of work-life balance and provide the flexibility you need to thrive
Fun Events: From team-building activities to company-wide celebrations, we love to have fun and recognize our hard work
Professional Growth: We support your career development with ongoing learning opportunities and the chance to take on new challenges
Work Hard, Play Hard: Enjoy a dynamic environment where your contributions are valued and your potential is unleashed

If you're excited about joining a vibrant, forward-thinking team and making a tangible impact, we want to hear from you! Send us your application. Please note that only candidates under consideration will be contacted. Let’s make great things happen together at KORT Payments!

About the company

KORT Payments provides an omnichannel payments platform that helps businesses connect and transact across channels with a focus on compliance, risk management, and payment processing. Its product is a full-stack, enterprise-grade platform that combines payments, risk controls, and regulatory compliance into a single system. The company differentiates itself through deep experience from a seasoned leadership team, a customer-focused approach, and the ability to tailor risk tolerance to each customer’s processing needs, offering strong relationship-based partnerships. The goal is to enable secure, efficient, and compliant payments for partners while growing satisfaction and long-term collaborations.

Company Size

11-50

Company Stage

N/A

Total Funding

N/A

Headquarters

Canada

Founded

N/A

Get referred to KORT Payments

See people who can refer or advise you

Simplify's Take

What believers are saying

Paythings claims 85-90% lower cash float and next-day deposits on May 28, 2026.
Tilled's July 8, 2025 partnership widened KORT's embedded-payments reach across North American ISVs.
KORT's active September 2026 publishing shows ongoing merchant acquisition and partner distribution efforts.

What critics are saying

KORT inherited Paysafe Direct's chargeback-heavy merchants on February 28, 2025, compressing margins.
Paysafe's transition services ended around August 2026, forcing KORT off legacy operational support.
Sponsor-bank de-risking can instantly choke KORT's high-risk merchant volume and revenue.

What makes KORT Payments unique

Joel Leonoff built KORT around Paysafe Direct's February 2025 merchant portfolio and compliance expertise.
Barnet Technologies added POS software in September 2024, deepening KORT's payments-plus-software stack.
The May 28, 2026 Paythings partnership extends KORT into cash handling for retailers.

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Benefits

Health Insurance
Dental Insurance
Vision Insurance
Flexible Work Hours
Remote Work Options
Professional Development Budget

Company News

PR Newswire

Oct 19th, 2026

KORT Payments to acquire AptPay to expand real-time payments in North America

KORT Payments, a Toronto-based omnichannel payments provider, has agreed to acquire 100% of AptPay, a Toronto payments technology company focused on real-time payments and payment orchestration. Terms were not disclosed. AptPay's platform lets businesses move money across multiple rails, including Interac e-Transfer, ACH, RTP, and FedNow, through a single integration. It also includes tools for Know Your Customer (KYC), Anti-Money Laundering (AML), and sanctions screening. The deal extends KORT beyond card acceptance into account-to-account payments and disbursements. It also speeds KORT's expansion in the US. AptPay will operate as a KORT division under its own brand, and chief executive officer Shams Syed will continue to lead it. The deal is expected to close in the fourth quarter of 2026, subject to customary closing conditions.

PayThings

May 28th, 2026

KORT Payments and Paythings modernize cash with smart safes, next-day deposit and lower costs.

KORT Payments and Paythings modernize cash with smart safes, next-day deposit and lower costs. AI-powered platform replaces manual cash handling and outdated logistics with real-time visibility and faster access to funds for retailers Toronto, ON - May 28, 2026 - KORT Payments (KORT), a leading omnichannel payments provider, and Paythings, an AI-powered cash operations platform, today announced a strategic partnership to bring Paythings' smart safe technology and cloud platform to retailers across Canada, introducing a more efficient way to handle and reconcile cash. Cash remains widely used in retail, but handling it still slows operations. Deposits are prepared manually, and access to funds can lag. Paythings captures cash at deposit and makes it visible immediately. The Smart Safe secures funds in-store, while the cloud platform records deposits in real time. Funds are available as soon as the next business day. "Retailers have been forced to work around outdated cash handling processes for too long," said Clifford Richstone, Chief Revenue Officer of Paythings. "We've built a system that changes how teams operate. Cash handling becomes faster and more reliable, without relying on manual steps." Through its collaboration with KORT, Paythings is extending this capability to retailers across Canada that are looking for a more efficient way to handle cash across one or multiple locations. "There's been very little innovation in how businesses handle physical cash," said James Good, Chief Revenue Officer at KORT. "What Paythings has built gives operators immediate visibility into their cash and a simpler way to manage it across locations. That has a direct impact on how efficiently stores run day to day." In practice, store teams spend less time preparing deposits and managers have a clear view of cash positions without waiting days for updates. Retailers using Paythings typically see: * 85-90% reduction in cash float with next-day deposit * 25-60% reduction in shrinkage after replacing manual counting * $500+ per month per location in savings from reduced deposit preparation and bank runs The platform maintains a complete audit trail for every deposit and surfaces unusual activity across locations. Paythings has processed billions in cash across multi-location retailers and is now bringing that experience to the Canadian market. About KORT Payments. KORT Payments (KORT) is a specialized omnichannel payments provider. Its core purpose is to enable businesses to connect and transact seamlessly through industry-leading capabilities in compliance, risk management, and payment processing. KORT is powered by its innovative full-stack, enterprise-grade platform and led by a seasoned management team. For more than 25 years, this team has been leading the charge in global e-commerce and payment processing. KORT is a customer-focused business dedicated to enhancing partner and customer satisfaction and building strong relationships. About Paythings. Paythings is a technology-first cash management platform that redefines how businesses handle physical currency. By combining secure smart safe hardware with AI-powered software, Paythings provides enterprise-level visibility, automated reconciliation, and predictive forecasting. The platform's cloud-connected ecosystem eliminates manual handling risks and optimizes working capital, turning traditional cash operations into a streamlined, data-driven asset. Paythings is dedicated to building the next generation of cash automation infrastructure, allowing partners and clients to manage physical and digital financial positions with total confidence.

PR Newswire

May 28th, 2026

KORT Payments partners with Paythings to bring AI-powered smart safes and next-day cash deposits to Canadian retailers

KORT Payments and Paythings have partnered to bring AI-powered smart safe technology to Canadian retailers, modernising cash handling operations. The collaboration introduces Paythings' cloud-connected platform, which captures cash deposits in real time and makes funds available by the next business day. The system replaces manual cash handling with automated reconciliation and real-time visibility across store locations. Smart safes secure funds in-store whilst the cloud platform records deposits instantly, eliminating traditional delays in fund access. Paythings, which has processed billions in cash across multi-location retailers, combines secure hardware with AI-powered software to provide enterprise-level visibility and predictive forecasting. KORT Payments, an omnichannel payments provider operating for over 25 years, will extend this capability to retailers seeking more efficient cash management across single or multiple locations.

PYMNTS

Mar 4th, 2025

Paysafe Looks To Digital Wallets To Fuel Growth In 2025

Paysafe says it is looking to its digital wallet business as a growth driver for the coming year.The payments company on Tuesday (March 4) released quarterly and full-year earnings showing revenue growth of a respective 1% and 6%.Total payment volume came to $40 billion for the quarter, a 12% increase, and $151.7 billion for the year, up 8%. Paysafe also projected revenue for the year of $1.71 billion to $1.73 billion, which fell short of analysts’ forecasts.Looking ahead to the remainder of the year, CEO Bruce Lowthers told analysts during an earnings call that the “overarching theme” the company is trying to leverage this year is its white label wallet.“And, so with that white label wallet platform, it gives us the opportunity to go into Peru, for example, where we have a really strong presence,” in eCommerce, the CEO said.Later in the call, Lowthers was asked about how Paysafe can differentiate itself from other players in the white label wallet space. He pointed to the company’s “regulatory strength” and strength around anti-money laundering (AML) issues.“We’re obviously regulated in Europe. We do a tremendous job around the AML issues, put a lot of effort into that,” he said.These efforts come as research by PYMNTS Intelligence shows digital wallets becoming the preferred choice for consumers around the world as cross-border transactions change.“From the U.S. to Saudi Arabia, people are leveraging digital wallets due to their fast and efficient way to send and receive money internationally,” PYMNTS wrote last month, following the publication of the report “Global Money Movement: How Digital Wallets Are Transforming Cross-Border Payments,” a collaboration with TerraPay.“This shift in payment preferences speaks to the demand for convenience and simplicity, the report notes, especially when compared to traditional methods like bank transfers or money transfer services.”Also on Thursday, Lowthers said the company had “no real comment” on a report from last month that it had received takeover interest.“You know, we’ve had some unsolicited proposals come in, inquiries come in. You know, we feel very good about the business,” the CEO said.“We feel like we’re creating a lot of value, with the business, but the board will…execute their fiduciary responsibility and take a look at anything that gets thrown over the rail.”Also in February, Paysafe said it was selling its direct marketing payment processing business unit, Paysafe Direct, to omnichannel payments provider Kort Payments, a company led by Paysafe’s founder and former CEO, Joel Leonoff.The transaction positions Paysafe to “sharpen our focus on Paysafe’s ideal customers and verticals in the experience economy,” Lowthers said at the time

PYMNTS

Feb 11th, 2025

Kort Payments To Acquire Paysafe’S Direct Marketing Payment Processing Business

Payments platform Paysafe Limited agreed to sell its direct marketing payment processing business line, Paysafe Direct, to omnichannel payments provider Kort Payments, which is led by Paysafe’s founder and former CEO, Joel Leonoff.The transaction includes reseller and merchant contracts, dedicated technology and employees related to the business, Paysafe said in a Tuesday (Feb. 11) press release.Subject to finalizing certain items related to transition services, the transaction is expected to close in 30 days, according to the release.The transaction positions Paysafe to “sharpen our focus on Paysafe’s ideal customers and verticals in the experience economy,” Paysafe CEO Bruce Lowthers said in the release.“The divestiture of our direct marketing payment processing business reflects our commitment to portfolio and resource optimization to focus on our largest growth opportunities as a company,” Lowthers said in the release. “This accelerates our transformation by exiting a non-strategic business line, bringing a close to the repositioning of our Merchant Solutions segment.”Kort Payments said in a Tuesday press release that its acquisition of Paysafe Direct furthers its “aggressive growth strategy” and “propels” the Canada-based company into the United States market.“The acquisition of Paysafe’s direct marketing payment processing business represents a quantum leap for the company and aligns with our commitment to providing innovative solutions across North America,” Leonoff said in the release. “The Kort team has extensive experience in managing complex industry verticals and has proven success in this sector.”Kort Payments provides compliance, risk management and payment processing services and has worked with companies in eCommerce and payment processing for more than 25 years, according to the release.The company acquired Barnet Technologies, a Canadian software company known for its point-of-sale systems, in September. Kort Payments said at the time in a press release that its team will scale Barnet’s technology, integrate that technology with its own payment platform and provide a holistic solution for clients.It was reported Thursday (Feb. 6) that Paysafe was considering a sale after getting takeover interest.During a November earnings report, Paysafe said it saw growth in core segments, gains in average transactions per active users of digital wallets and expanding reach in Europe

KORT Payments

Risk Investigator 2

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