Recent Developments and Their Importance

As reported by Forbes, Checkout.com has reached a $12 billion valuation while focusing on the next generation of AI-based commerce, particularly in the realm of AI shopping agents that assist consumers in navigating the open web to discover, choose, and purchase items.

This headline carries significant weight for two main reasons:

• It establishes a new valuation baseline for Checkout.com following the remarkable fintech boom of 2021-2022, during which the company secured $1 billion at a $40 billion valuation (CNBC).
• It represents a strategic pivot toward AI shopping agents—software capable of researching products, comparing prices, and completing transactions, which could fundamentally alter the payment landscape.

Should agent-driven shopping become mainstream, payments will evolve from a simple button click to a more complex interplay of reliable APIs, identity verification, and trust signals, allowing machines to act on behalf of consumers. A payment processor that can efficiently secure these machine-led transactions will become essential for merchants.

AI Shopping Agents: What You Need to Know

AI shopping agents are either fully autonomous or semi-autonomous tools designed to assist users in the shopping process. Imagine these agents as dedicated, context-aware assistants that can interpret user intent, browse various options, ask pertinent questions, and finalize purchases once the user provides approval. Noteworthy examples include:

• Amazon’s Rufus, a generative AI shopping assistant integrated into the Amazon app, aimed at answering product inquiries and offering tailored options (Amazon).
• Google’s enhanced use of AI across Shopping and Search, linking user queries to product information through the Shopping Graph and AI Overviews (Google).
• Shopify’s AI features such as Shopify Magic and Sidekick, which assist merchants in creating content and optimizing store management, with the Shop app reshaping the discovery process (Shopify).

Why are we seeing this shift now? Three main factors have converged:

• Advancements in generative AI, which now allows for agents capable of parsing unstructured data, reasoning through choices, and planning multi-step tasks (McKinsey).
• Increased consumer trust in digital payments, bolstered by innovations in tokenization, biometrics, and improved fraud prevention measures from networks and processors (Visa, Mastercard).
• Merchants are looking for ways to boost conversion rates while lowering customer acquisition costs, and AI agents provide a seamless experience that reduces friction between intention and purchase.

In essence, as searches become more conversational and product discovery evolves into a personalized experience, the checkout process is transitioning to a more ambient model. Payments partners that enable agents to finalize purchases securely and consistently will be highly sought after.

The Significance of Checkout.com’s $12B Valuation

Checkout.com, based in London, is a payments platform recognized for card processing, diverse payment options, fraud prevention tools, and its ability to support digital-first businesses globally. Following a surge to a $40 billion valuation in early 2022, the company—like many in the fintech space—has been recalibrating due to a more challenging funding landscape (CNBC).

The newly established $12 billion valuation signals two key insights: a realistic assessment of current market expectations and a strong belief in the potential for AI shopping agents to be the next catalyst for growth. This shift suggests a transition from merchant-controlled interfaces to agent-driven purchasing pathways, benefiting processors that excel in:

• Identity and risk management—verifying buyers, devices, and intent with minimal friction.
• Tokenization and wallet solutions—securing and utilizing payment credentials across various merchants and regions without compromising security.
• Authorization optimization—enhancing approval rates through data utilization, network tokens, and smart retry mechanisms.
• Scalable compliance solutions—automating the management of Strong Customer Authentication (SCA), 3D Secure 2 (3DS2), chargebacks, and evolving local regulations.
• Developer-friendly APIs—facilitating seamless, reliable, and safe payment integrations for agents.

These are core competencies for Checkout.com and represent a natural extension of the platform’s role for enterprise merchants. The pressing question now is who will emerge as the most “agent-friendly” processor.

Imagining Agent-Driven Checkout

Agentic checkout redefines traditional methods, focusing on protocols rather than simple button clicks. Here’s a potential flow:

1. A user prompts an assistant: “Find a pair of neutral-support running shoes under $120 that can arrive by Friday.”
2. The agent explores multiple retailers, compares options, checks delivery times, reads reviews, and presents a shortlist.
3. The user selects an option with quick approval: “Purchase the Asics in size 10, shipping to my work address.”
4. The agent retrieves a stored payment credential, conducts risk assessments, and completes the order through a payment API.
5. The agent monitors the shipment and manages any returns or refunds, keeping the user informed throughout the process.

For this model to function efficiently across the open web, the payment infrastructure must handle identity verification, risk management, tokenization, and compliance seamlessly. Processors that can streamline these elements for agents will aid merchants in converting high-intent buyers without having to overhaul their entire checkout systems.

What This Means for Merchants

Adopting agent-friendly payment systems will reshape strategy, technology, and operations for merchants. Here’s how to get ready:

1) Ensure Product Data is Accessible to Agents

• Keep your product data structured, accurate, and current. Comprehensive, machine-readable metadata enhances the likelihood that an agent can align your offerings with user intent.
• Whenever possible, provide real-time inventory and shipping timelines. Agents prefer options they can fulfil with confidence.

2) Provide Diverse Payment Options

• Complement card payments with popular digital wallets and regional alternatives. Agents will typically default to the combination that maximizes approval rates and minimizes friction for each user.
• Implement network tokenization and best practices for saving card information with your payment processor to improve authorization rates and decrease fraud (Visa).

3) Strengthen Identity Verification and Trust

• Gracefully implement step-up authentication using 3DS2 and passkeys as needed, particularly under PSD2 SCA regulations in Europe and similar frameworks elsewhere.
• Ensure clear consent is obtained for agent-initiated activities and provide transparent receipts and controls.

4) Analyze Performance from Agent-Led Activities

• Monitor sessions driven by agents and their outcomes to gauge conversion rates, returns, and support efforts compared to traditional channels.
• Test various pricing strategies, bundling options, and post-purchase processes tailored for agent-driven interactions.

Competitors in the Agentic Space

Checkout.com is not the only player eyeing the future of agent-driven commerce. Several competitors are also making headway:

• Stripe – Expanding payment optimization, network tokenization, and risk management tools, with robust developer engagement and increasing AI functionalities for merchants.
• Adyen – Focusing on unified commerce, integrated payments, and risk mitigation, excelling at global enterprise scale.
• PayPal – Investing in wallet features, one-click checkout options, and merchant services that can be utilized by agents behind the scenes.
• Major Platforms like Amazon, Google, and Shopify are implementing native assistants that could influence product discovery and potentially establish agent-to-merchant standards over time.

The crucial question remains: Will agent-driven commerce centralize within a few dominant platforms, or will it maintain an open model across the web? A payment processor capable of simplifying agent interactions across the open web will provide significant advantages for merchants seeking both independence and reach.

Regulatory Frameworks and Trust Issues

The rise of agent-led checkout interacts with existing payment regulations and emerging AI policies.

• Payment Regulations – In the EU and UK, PSD2 SCA has already transformed authentication processes, while upcoming reforms under PSD3 and the Payment Services Regulation aim to further enhance fraud mitigation and data access (European Commission).
• Data Minimization – Agents must limit data storage and transmission to only what is necessary for payment and fulfillment, ensuring clear consent controls and revocation capabilities.
• Transparency Requirements – When agents select specific products or merchants, both consumers and regulators may demand a clear rationale, especially if affiliate economics are involved.

Payment partners equipped with robust compliance tools, chargeback management, and audit-friendly systems will assist merchants and developers in navigating these requirements effectively.

Foundational Elements of Agent-Friendly Payments

Implementing a reliable agent-to-merchant checkout experience will draw on existing standards and emerging capabilities:

• Payment APIs and Orchestration – Consistent endpoints for authorizations, captures, refunds, and payouts that are accessible and clear to both users and agents.
• Identity and Authentication – Utilizing device signals, risk assessments, and passwordless options such as passkeys and WebAuthn to comply with SCA while minimizing user friction.
• Tokenization and Secure Vaulting – Employing network and merchant tokens to enhance security and approval rates while minimizing exposure of sensitive payment details (Mastercard).
• Browser-Based Payment Standards – Utilizing the W3C Payment Request API and related specifications to streamline the payment collection process within browsers (W3C).
• Consent and Permissions Management – Clear designation of scopes and time-limited approvals for agent-initiated payments, along with user controls to review and withdraw consent.

The next step involves integrating these components so that agents can confidently operate across a wide range of merchants rather than being confined to isolated environments.

Opportunities and Challenges in the Coming 24 Months

Benefits

• Increased Conversion Rates – Agents streamline the research and checkout processes, reducing the likelihood of cart abandonment.
• Improved Personalization – Assistants can assess user preferences, ethical considerations, and logistical challenges in real-time.
• Lower Customer Acquisition Costs – Merchants can attract customers through agent recommendations instead of relying solely on paid advertisements.

Challenges

• Errors and Misorders – Agents might misinterpret product specifications, leading to returns and increased customer support demands.
• Fraudulent Activities – New transaction flows could expose vulnerabilities, such as synthetic identities and compromised agents.
• Platform Dependency – Merchant visibility may increasingly rely on a few dominant agent providers unless open standards are promoted.

Ultimately, trust—not just novelty—will dictate which agent-driven commerce experiences become successful. The payments stack is where this trust is cultivated daily.

What to Monitor Moving Forward

• Agent-to-Merchant APIs – Look for standardized means to present catalog data, pricing, inventory, and shipping information to agents.
• Wallet-Native Agents – Anticipate deeper integration of agents with platforms like Apple Pay, Google Pay, and card network tokenization.
• Authentication User Experience – Expect passkeys and biometric authentication methods tailored for agent-driven transactions.
• Clarification on Regulations – Seek out guidance on consent, transparency, and responsibility in agent-mediated purchases.
• Partnerships among Payment Processors – Look for collaborations between AI platforms and payment providers to ensure high approval rates and comprehensive coverage.
• Merchant Guides – Best practices for pricing strategies, bundling, and post-purchase processes tailored to agent-driven user intentions.

The Bottom Line

Checkout.com’s reset to a $12 billion valuation combines pragmatic outlooks with a focused vision: agent-driven shopping is on the horizon, and those who can ensure it is safe, rapid, and reliable at a global scale will prevail. For merchants, the time to begin practical preparations is now, focusing on enhancing product data, diversifying payment methods, reinforcing identity verification, and implementing metrics to gauge agent-driven demand.

The evolution of payments will favor those who can effectively translate consumer intent into trusted transactions. If agents represent the new entrance point in commerce, processors will become the essential infrastructure that guarantees security and functionality.

Frequently Asked Questions

What insights did Forbes share about Checkout.com?

Forbes highlighted that Checkout.com has reached a $12 billion valuation while investing in AI shopping agents as a primary growth driver after peaking at a $40 billion valuation in early 2022 (Forbes, CNBC).

Can you explain what an AI shopping agent is?

An AI shopping agent is a digital assistant capable of researching products, comparing prices and delivery options, and completing purchases on behalf of users with their permission. Examples include Amazon’s Rufus and various AI functionalities within Google Shopping and Shopify (Amazon, Google, Shopify).

How do payment processors facilitate agent-driven shopping?

They provide APIs and risk management tools that allow agents to access stored credentials, authenticate users when necessary, tokenize payment information, optimize transaction routing, and comply with regional regulations like PSD2 SCA in Europe.

What are the potential risks of agent-led checkout?

Major risks include inaccuracies in orders stemming from AI errors, new fraud behaviors, unclear accountability for mistakes, and extensive reliance on specific platforms. Effective consent measures, robust risk oversight, and clear user experiences are key to mitigating these challenges.

How can merchants start preparing now?

Merchants should focus on improving the quality of product data, supporting various payment methods, adopting tokenization techniques, implementing passkeys and 3DS2 for enhanced authentication, and separately tracking the performance of agent-driven interactions.

References

1. Forbes – Checkout.com Hits $12B Valuation, Bets on AI Shopping Agents
2. CNBC – Checkout.com Raises $1B at $40B Valuation (2022)
3. Amazon – Introducing Rufus, a Generative AI Shopping Assistant
4. Google – AI Overviews in Search
5. Shopify – Announcing Sidekick
6. McKinsey – The Economic Potential of Generative AI
7. Visa – Tokenization Overview
8. Mastercard – Tokenization Overview
9. W3C – Payment Request API
10. European Commission – Retail Payments Package (PSD3/PSR Proposals)