Future: TipTop May Redefine Payments

In December of last year, I proposed a novel concept to a returns management software company. I suggested that adding an exchange function to their technology stack would shape the industry by promoting a method of reCommerce and a post-purchase marketplace led by the company’s many direct-to-consumer clients currently using the software to simplify returns.

The idea’s crux was built on a critical issue rapidly gaining momentum: microplastics management. This environmental challenge pushes companies to reconsider their approach to product returns, recycling, and resale. The essence of my proposal was simple: companies need systems to upcycle and recycle materials, leveraging these efforts for tax incentives, public goodwill, or even profit. I ended the proposal with the following words (edited for brevity):

This idea is infinitely scalable and will be a prominent business with or without [company]. But you are positioned with several advantages and a head start to include: existing portfolio of companies to offer the service, a brand that suggests the power of upcycling, a network of potentially interested partners who can help you facilitate. I just happen to believe that this can transform [company] – moving it to a higher plane. And it can transform the industry that I love with all of my heart.

The proposal was scalable, innovative, and essential to addressing the growing microplastics crisis in the fashion industry. My proposal to the returns management company was not accepted. Fast-forward to the fourth quarter of 2024 and a better solution has been brewing for nearly three years. TipTop is a venture-backed development billed as a payments solution from Postmates founder Bastian Lehmann.

Recycled goods can be a downpayment on future purchase.

Lehmann’s TipTop is taking bold steps to reimagine the lifecycle of consumer goods: how they’re sold, acquired, and ultimately resold or recycled. With the rise of reCommerce (the resale of products), TipTop’s new payment system is an answer to a forward-thinking vision, one that aligns sustainability with profitability in the world of fast-moving consumer goods. Tiptop is designed to make it easy to resell and repurpose items and is not only a business model innovation but it can be a solution to an environmental dilemma that has been long overlooked until recently. On September 24, The Guardian published this legislative news on textiles in the state of California:

If passed, Californians will be able to bring unwanted and even damaged apparel and household textiles to thrift stores, charities and other accessible collection sites throughout the state for sorting and recycling. This first-in-the-nation bill, known as the Responsible Textile Recovery Act, requires producers of apparel, towels, bedding and upholstery to implement and fund a statewide reuse, repair and recycling program for their products. [cite]

It doesn’t require tremendous vision to see how TipTop’s payments architecture could replace altruism-alone for a more profitable version.

How It Works: The Power of TipTop’s Payment System

TipTop’s system addresses a fundamental problem in the retail ecosystem: it’s easier to buy than it is to sell. Consumers accumulate products—tech gadgets, clothing, accessories—often with no clear pathway for reselling or discarding them responsibly. Lehmann identified this gap and seized upon the opportunity to create a two-pronged platform that leverages consumer habits for both immediate monetary returns and longer-term resale plans.

With TipTop, users can receive instant cash offers for their old products, like electronics or fashion items, simply by connecting their Gmail or Amazon accounts. The platform scans for eligible items and predicts their resale value. This seamless experience removes the friction of traditional resale models, where consumers often have to stage, price, and list their items across multiple platforms like eBay or Facebook Marketplace. TipTop brings liquidity to this otherwise sluggish market, offering sellers cash in hand, while a delivery service picks up the product.

But TipTop’s real innovation is its payment solution, TipTop Pay, where the system allows buyers to receive an upfront discount on new items in exchange for committing to return them after a fixed period. This introduces an entirely new way to think about consumption—a shift from ownership to usage, akin to the “buy-now-pay-later” models that have reshaped retail finance. TipTop resells these items in bulk to wholesalers or via third-party marketplaces like eBay, creating a virtuous cycle of consumption and resale. If this vision can become a reality – at scale – it will revolutionize retail in ways yet to be seen.

For brands, this model is a game-changer. They can capture value from products after their initial sale, extending the lifecycle of goods and reducing the environmental impact associated with waste and overproduction. The speed of liquidity for the consumer is the “killer app.” And back to that sense of altruism, this concept ties directly to the need for sustainable initiatives I outlined in my original proposal: brands must move toward recycling, upcycling, and innovative disposal methods for microplastic-laden products to remain competitive and appease a more eco-conscious consumer base.

ReCommerce and Environmental Responsibility

The rise of reCommerce, or the resale of goods, is not just a trend but a critical business strategy for fashion and consumer brands navigating an era of heightened environmental awareness. As I noted in my 2023 study on the subject, the fast fashion and athleisure sectors are facing increasing scrutiny for their reliance on non-biodegradable synthetic fibers. By 2050, it’s estimated that 590 million tons of plastic will be produced annually, much of which will end up in landfills or the ocean.

Legislative intervention, such as the aforementioned California’s Responsible Textile Recovery Act, is creating pressure for brands to address the environmental impact of their products. TipTop’s solution offers the path forward without relying on government, enabling brands to monetize the resale of their products while simultaneously contributing to a reduction in waste. By simplifying the process for consumers to return goods, and by providing a scalable marketplace for brands to resell items, I believe that TipTop aligns financial incentives with environmental responsibility.

This connection between reCommerce and sustainability is already evident in the actions of major players in the retail space. Brands like Patagonia, Levi’s, and Nike have introduced their own resale platforms, recognizing that the resale value of their products is an important metric for both sustainability and consumer loyalty. However, for smaller brands without the resources to build proprietary resale platforms, a solution like TipTop offers the same benefits without the infrastructure investment. And even the larger enterprise brands don’t have veriable, speedy liquidity built into their models.

A Solution for Microplastic-Fueled Industries

Industries heavily reliant on synthetic fibers: athleisure, fast fashion, and performance wear – are the most at risk in this new regulatory environment. As consumers become more aware of the health risks associated with the build up of microplastics in landfills and waterways, and as governments begin to legislate against this accumulation, brands will need systems in place to manage product lifecycles responsibly.

TipTop’s resale model offers a unique advantage for these brands. By facilitating the resale of synthetic products, it extends their lifecycle, potentially offsetting the negative environmental impact of their initial production. Moreover, as brands adopt recycling and upcycling strategies, TipTop’s system could evolve to accommodate returns of materials for recycling or resale: closing the loop on product lifecycles.

In this way, TipTop could answer one of the most pressing challenges facing the fashion industry: how to monetize sustainability. By creating a frictionless way for consumers to resell items, the platform not only encourages responsible consumption but also provides brands with a new revenue stream and a powerful marketing tool. Brands that adopt this model can position themselves as leaders in the sustainability space, differentiating themselves from competitors who continue to ignore the issue.

Smarter Than What I Envisioned

When I proposed to a returns management company in 2023 that they take ownership of the recycling and material return initiatives for microplastic-heavy brands, I knew that the conversation around fast fashion and environmental responsibility was only beginning. What I couldn’t have predicted was how quickly a solution like TipTop would emerge to fulfill that vision. Transactional ease for the consumer positively influences demand for the trade

TipTop represents the intersection of technological innovation and enviro-economic necessity. It’s a system that not only simplifies the resale process for consumers but also creates a viable, scalable solution for brands looking to reduce their environmental impact. Whether through electronics or fashion: the rise of reCommerce will define the next decade of retail, offering a new way for brands to engage with consumers and a new way for consumers to think about their role in the lifecycle of the products they buy.

As TipTop’s payment system gains traction, it may become the standard for brands seeking to integrate reCommerce-led sustainability into their business models. And for those brands that are ready to embrace this shift, the opportunity is clear: not only to meet consumer demand for more sustainable practices but also to monetize those efforts in ways that benefit each their bottom lines, consumers, and the planet. TipTop can shape sustainability and recommence by redefining payments.

Research, Data, and Writing by Web Smith

Memo: Lessons for the eCommerce Space

Klarna is making waves again—but this time for something much bigger than installment payments. The Swedish fintech giant has boldly declared that artificial intelligence (AI) is not just an enhancement but the future. This assertion is not merely a marketing ploy; Klarna is actively reshaping its workforce and operations in line with its AI-driven ambitions. With a target to reduce its full-time workforce by more than 50%—from 5,000 to 2,000 employees—CEO Sebastian Siemiatkowski has made it clear that this shift is central to the company’s strategy for the future. But what does this mean for larger enterprise software companies, particularly in the eCommerce space?

A Turning Point for Klarna

Klarna’s embrace of AI goes beyond surface-level adjustments. The company has made substantial gains, reporting significant revenue growth and operational efficiency due to AI initiatives. According to Siemiatkowski, the company can “do much more with less.” For example, Klarna has reduced its workforce to 3,800 employees, down from a peak of 5,000, and plans to further reduce that number. Yet, despite the reduction in human resources, the company’s revenue per employee has skyrocketed, increasing from SEK 4 million ($393,000) to SEK 7 million ($689,000) in just one year. These figures are a direct testament to the power of AI to replace inefficiency, drive productivity, and boost profitability.

Klarna is at the very forefront among our partners in AI adoption and practical application. Together we are unlocking the vast potential for AI to boost productivity and improve our day-to-day lives.

Brad Lightcap, COO of OpenAI

The company’s most headline-grabbing innovation has been the development of an AI-powered chatbot, built in collaboration with OpenAI. This chatbot handles the workload equivalent of 700 customer service agents. Klarna also projects $40 million in profit improvements from its AI initiatives in 2024 alone. While this showcases the effectiveness of AI in operational roles, the narrative extends beyond cutting costs and workforce downsizing—it highlights AI’s potential to dramatically transform businesses, particularly as Klarna prepares for a long-awaited IPO.

The Drive Toward Profitability

For Klarna, the pursuit of profitability is nothing new. Between 2007 and 2018, the company reported profitable yearly results, peaking with SEK 523 million ($61 million) in earnings before tax in 2017. However, the past few years saw Klarna experience losses as it aggressively expanded into new markets. With large investments in its Visa-issued Klarna card and several acquisitions, including the now-defunct New Zealand arm of Laybuy, Klarna sought to scale quickly, broadening its market reach and market depth. Artificial Intelligence aside, this physical credit card move is just as fascinating.

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Klarna’s foray into the physical payments space with the Klarna Visa is an interes58ht testament to the company’s innovative approach to embedding the BNPL model into consumers’ everyday lives. The Klarna Visa, unlike traditional credit cards, charges no interest and instead converts every purchase into a BNPL transaction, requiring payments in four bimonthly, interest-free installments. Running on the Visa network, it allows users to transform any purchase made at merchants that accept Visa into a manageable installment plan, expanding the reach and appeal of the BNPL model.

While these moves brought returns—such as increased market penetration and a larger share of the BNPL market—Klarna’s strategy came at a cost. AI presented itself as a lifeline to reestablish profitability.

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Klarna’s AI-Led Workforce Reductions

One of the more controversial aspects of Klarna’s AI transformation has been its impact on the workforce. Since the company stopped actively recruiting for non-engineering roles, headcount reductions have primarily occurred through natural attrition. Departing employees are not replaced, and their work is absorbed by AI tools. Siemiatkowski’s “directional” target of 2,000 employees hints at further cuts, even as he avoids specifying a deadline.

The most visible impact of this shift has been in customer service. Klarna’s AI assistant, launched in early 2024, now handles two-thirds of the company’s customer service chats, matching the efficiency and customer satisfaction levels of its human counterparts. The average time to resolve customer inquiries has dropped from 11 minutes to 2 minutes, a significant improvement that demonstrates how AI can optimize traditionally human-led processes.

The AI assistant’s success has extended beyond customer service. Klarna has saved millions by reducing reliance on photographers, image banks, and marketing agencies, with the marketing team reporting higher productivity despite a reduction in size. AI is also employed across departments like communications, marketing, and legal, further streamlining operations.

Challenges and Drawbacks of Klarna’s AI Approach

Despite its financial successes, Klarna’s aggressive use of AI has not been without challenges. Internally, some employees report burnout and frustration with increased workloads, as fewer staff are left to handle the non-automatable aspects of their roles. Employee satisfaction ratings have dipped significantly, with Glassdoor reviews showing an average rating drop from 3.8 in 2022 to 3.0 in 2024. Several reviews highlight concerns over high workloads, stress, and a lack of pay raises or career progression.

And externally, Klarna’s vocal AI strategy has sparked concerns among the public. While AI’s potential to replace jobs is widely recognized, many view the rapid workforce reductions as a threat to job security. Though social media has amplified some outrage, there is no concrete evidence yet that this backlash has impacted Klarna’s sales or customer engagement.

There are also legal and ethical concerns surrounding AI-generated content. Klarna’s decision to reduce employment in roles like photography and design raises questions about potential copyright infringements, as AI-generated work can often replicate existing material without proper attribution. OpenAI, Klarna’s AI partner, is currently embroiled in lawsuits over copyright issues, with outcomes that could shape how companies using AI handle intellectual property disputes in the future.

Lessons for eCommerce and Enterprise Software

Klarna’s AI-led transformation offers valuable lessons for the broader e-commerce and enterprise software sectors. First and foremost, it highlights the immense potential of AI to streamline operations, reduce costs, and drive profitability. Klarna has leveraged AI not only to cut jobs but also to improve efficiency across its entire business, from customer service to marketing.

For other companies, especially those operating at large enterprise scales like Salesforce or Workday (both of which Klarna has ended partnerships with), the question is how to integrate AI without sacrificing employee morale or risking a public relations fallout. Klarna’s approach has been fast and aggressive, driven by the looming IPO. While this might work in the short term, companies looking to adopt AI should consider a more measured approach that balances automation with employee well-being.

While the company has seen tremendous financial benefits, it is still navigating the complexities of employee satisfaction and public perception. As AI continues to evolve, companies will need to develop strategies that leverage its benefits while addressing its potential drawbacks.

If Klarna’s AI-driven trend continues, we could see a significant shift across the eCommerce and SaaS landscape. Companies may increasingly adopt in-house AI solutions, leading to widespread cost reductions, workforce downsizing, and reduced reliance on traditional third-party service providers. Here are 10 DTC industry SaaS companies that could be impacted by AI innovations as businesses begin to bring these capabilities in-house to manage costs more efficiently:

Klaviyo
AI advancements could enable companies to develop personalized communication systems in-house, reducing their need for third-party solutions.

Yotpo
In-house AI tools could streamline content generation, review management, and even customer rewards, making Yotpo’s services less essential.

Gorgias
With advanced AI, brands could build internal customer service automation systems, reducing dependence on platforms like Gorgias for managing queries and tickets.

Attentive
As AI improves personalization and engagement, companies might develop their own messaging platforms, minimizing the need for external SMS marketing providers.

Loop
AI-powered solutions could give DTC brands the ability to manage returns internally, optimizing logistics without external software.

Kustomer
In-house AI could streamline customer service and data management, reducing the need for third-party CRM tools.

Privy
As AI enhances lead generation and conversion strategies, businesses could develop these capabilities internally, eliminating the need for external tools like Privy.

Recharge
AI-driven solutions could allow businesses to develop and manage their own subscription services, reducing the reliance on external billing platforms.

Bold Commerce
AI could enable businesses to build personalized checkout and upsell systems internally, eliminating the need for SaaS platforms like Bold Commerce.

Zendesk
With AI advancements in natural language processing, brands may build in-house support solutions to handle inquiries and resolve issues without the need for a third-party platform like Zendesk.

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I believe that Klarna’s bold bet on AI signals a future where it plays an even more central role in cost management and profitability. The company’s rapid adoption of AI tools has allowed it to reduce costs, increase revenue, and position itself for a successful IPO.

For larger-scale enterprise software companies, Klarna’s example offers both inspiration and caution. AI has the potential to transform industries, but it must be implemented thoughtfully, with an eye toward the long-term impacts on employees and society at large. In the end, Klarna’s AI journey may serve as a blueprint for others, but only time will tell how sustainable its rapid transformation truly is.

Research, Data, and Writing by Web Smith 

Memo: Active Listening and Retail Media

The digital marketing world has evolved to fit the times but it’s evolving far faster than public knowledge has been made aware. The data available to the most savvy marketers far exceeds the potency of what existed at Facebook’s third-party advertising peak. It leaves the latest iteration, first-party data far behind. This months old anecdote by James Heurcher of AdExchanger adequately sums up the struggling promise of first-party data:

The promises of first-party data and individual personalization are alluring, he said. What vendors don’t mention is its super-fast half-life: first-party cookies and device IDs disappear, IP addresses change, emails turn out to be placeholder spam accounts. And through it all, ad blockers prohibit many one-to-one marketing use cases.

Operations are finding workarounds using increasingly sophisticated, open-sourced intelligence-based approaches. This summarizes one of several that I am aware of. Identifiable data is acquired at a premium; one of the most prevalent forms comes through active listening, which has emerged as a solution, according to recent reports and documents. The technology leverages real-time interpersonal conversations to build precise, hyper-targeted advertising campaigns. Cox Media Group (CMG) is at the forefront of this innovation, whose Active Listening technology claims to collect voice data from smart devices and pair it with behavioral insights to target consumers who are “ready to buy.” While the concept sounds futuristic, it also raises concerns about privacy and the boundaries of data collection.

According to reporting by 404 Media, CMG’s pitch deck (view here) reveals how voice data is allegedly sourced from device microphones. However, it is unclear which specific devices are involved—whether smart speakers, televisions, or smartphones. The company’s strategy relies on AI to process this data, enabling advertisers to reach potential customers before competitors do. CMG claims to work with 470+ data sources, combining voice and behavioral data to create highly targeted audience lists that can be uploaded into major ad platforms like Google, Facebook, Amazon, and Bing.

The Mechanics of Voice-Driven Ad Targeting

The core of CMG’s pitch centers on its ability to capture real-time intent data by listening to conversations near device microphones. This voice data is processed through AI and enriched with other behavioral insights to generate a list of consumers who are ready to make a purchase. Once the list is created, advertisers can target potential customers through a variety of channels, including streaming TV, audio, display ads, and social media.

This precision targeting comes with a price: $100 per day for a 10-mile radius, or $200 per day for a 20-mile radius. By geo-targeting consumers within a specific area, businesses can serve ads to the right audience at the right time, significantly improving the effectiveness of their campaigns. According to the pitch deck, CMG promises that this approach not only reduces click and acquisition costs but also enables advertisers to generate lookalike audiences at a fraction of the typical cost.

A Partnership Network in Question

In its pitch, CMG positions itself as a leader in digital marketing, citing key partnerships with tech giants such as Google, Facebook, and Amazon. According to the 404 Media report, CMG boasted of being among the first media companies to become a Facebook marketing partner and the first-ever media partner for Amazon Advertising. Additionally, CMG claimed to be a Google Premier Partner, which places it in the top 3% of advertisers.

However, these claims have come under scrutiny. Google has since removed CMG from its Partners Program following an inquiry by 404 Media, signaling potential violations of Google’s advertising policies. In a statement to 404 Media, Google emphasized that all advertisers must comply with applicable laws and regulations. Amazon also distanced itself from the program, stating that it has never worked with CMG on Active Listening and has no plans to do so in the future. Meta (Facebook’s parent company) has been more cautious, stating that they are reviewing whether CMG’s use of voice data violates their terms and conditions.

The Ethical Debate: Privacy Concerns and Transparency

The concept of using voice data from everyday conversations for targeted advertising inevitably raises ethical questions, at the very least. How much are consumers aware of how their data is being used? And more importantly, where is the line between personalized advertising and invasive surveillance? CMG’s technology sits at the center of this debate, especially as it gains traction in a world where privacy laws are tightening and consumers are becoming more protective of their personal data.

When 404 Media first reported on CMG’s Active Listening capabilities, the company’s website openly advertised the service with provocative language: “No, it’s not a Black Mirror episode—it’s Voice Data, and CMG has the capabilities to use it to your business advantage.” That page was subsequently removed following the initial media coverage, leaving more questions than answers about the future of this controversial advertising approach.

Further complicating the matter is a related report by 404 Media involving MindSift, a smaller company that similarly boasted about using voice data to target ads through smart speaker microphones. After the revelations, MindSift quickly wiped any mentions of this capability from its social media platforms, raising concerns about how many companies are quietly exploring this invasive form of data collection.

A Competitive Edge with Active Listening—But at What Cost?

From a business perspective, CMG’s Active Listening offers clear advantages. By being able to pinpoint when a consumer is discussing a need for a product or service, advertisers can deliver highly personalized, contextually relevant ads in real-time. This precision not only drives higher conversion rates but also reduces advertising spend on irrelevant audiences.

Yet, as 404 Media points out, this technological capability also raises significant concerns about data transparency and the potential misuse of voice data. Companies looking to use Active Listening as part of their advertising strategy must tread carefully, ensuring compliance with privacy regulations and being transparent with consumers about how their data is being collected and used.

The Future of Voice Data in Advertising

While CMG’s voice-driven ad technology promised to reshape how brands reach consumers, it also faces considerable hurdles, both from a regulatory and consumer trust perspective. As Google, Amazon, and Meta reevaluate their relationships with CMG, the broader industry will need to reckon with the ethical implications of using voice data for commercial gain.

For brands, the decision to engage with this type of technology requires careful consideration of both the potential ROI and the risk of alienating consumers. In a world where privacy is increasingly valued, the future of voice data in advertising will likely be shaped as much by public perception as it will by technological advances.

On May 21, a company called Audacy, Inc. posted the following:

Among those likely to use voice to interact with ads, most would likely to get additional information (71%) or learn about deals (62%). Almost half (46%) of those interested in voice-based interactions would go ahead and complete a purchase.

And who are the voice shoppers of today? They are high-income suburbanites with smart speakers at their homes. They are almost universally streaming audio, with more than half listening to podcasts weekly. Women tend to be the more cautious, but smart shoppers: Among those interested in voice ads, information- and deal-seekers (59%) skew female, men (53%) are slightly more likely to purchase with voice. [CITE]

The above feels innocuous but the part that went unsaid is that it’s the high-income suburbanites with smart speakers in their homes that are supplying this trade. Active Listening technology may be a powerful tool in the marketer’s arsenal, but it also pushes the boundaries of consumer privacy. The involvement of companies like Google and Amazon in distancing themselves from this practice suggests that the risks might outweigh the rewards. For now, brands considering this technology must weigh the benefits of hyper-targeted ads against the ethical and legal scrutiny that will undoubtedly follow.

By keeping an ear to developments in this space, marketers can better navigate the future of voice-driven advertising, ensuring that they remain compliant with regulations while also respecting consumer trust.

Research, Data, and Writing by Web Smith