PeakSpan’s Investment Thesis for PrettyDamnQuick

PeakSpan’s supply chain software team is thrilled to have led a $25M Series A growth financing in PrettyDamnQuick (or “PDQ”), a shipping and checkout personalization platform for e-commerce brands (press release).

The online shopping experience has evolved dramatically, now generating vast amounts of data at every stage of the customer journey. Brands have long leveraged this telemetry — ranging from browsing behaviors to purchase history — for marketing, targeting, and product positioning, primarily focusing on top-of-funnel engagement. However, as personalization and optimization in areas like product recommendations, email, and advertising have become table stakes, a lucrative area within the shopper journey has remained overlooked until recently: checkout. This is largely due to the complexity of converging supply chain, payments, and commerce technologies into a single, high-stakes moment for the shopper. Led by the likes of Amazon, checkout is rapidly becoming the “belle of the ball” with respect to where brands are investing time and energy due to the high-impact nature of this moment in the shopping journey.

Amid this shift, PrettyDamnQuick has emerged as a leader in checkout optimization, filling this gap by bringing advanced capabilities (once exclusive to giants like Amazon) into the hands of brands selling direct-to-consumer from their own website. As platforms like Etsy, Walmart, and Target invest in personalized checkout flows to meet evolving consumer expectations, these capabilities remain inaccessible for the majority of the 30 million online merchants. For the largest brands and marketplaces in the ecommerce arena, hiring an entire team of data scientists and allocating millions of dollars in development resources dedicated to optimizing and personalizing the checkout experience is a potentially worthy investment. However, for most merchants, the cost and complexity of optimizing shopper checkout experiences is prohibitively high. Brands that can leverage shopper, item-level, and logistics-related data to optimize and personalize the consumer checkout experience stand to benefit tremendously (while those that do not are currently forfeiting ~$260B in incremental revenue annually).

PDQ has developed a highly sophisticated and configurable platform, ingesting dozens of data sources and analyzing millions of checkout sessions to power its A/B testing capabilities. PDQ not only suggests but also directly implements dynamic and targeted strategies in real-time across various ecommerce platforms (e.g. Shopify, Commerce Cloud, CommerceTools, etc.), enabling merchants to transform their checkout process into a powerful driver of customer satisfaction, loyalty, and incremental growth. PDQ is instrumental in uplifting customer lifetime value by increasing average order values, checkout conversion, and customer repurchases, creating profitable shipment routes, and increasing customer satisfaction (average PDQ ROI of 10x). From a category evolution and positioning perspective, checkout personalization is often described as “cutting edge” — a segment we anticipate will become as prolific as targeted advertising, particularly for brands processing higher volumes of orders per month, where data volume is sufficient for statistically significant testing and delivers clear ROI.

PDQ’s personalization engine utilizes dynamic shipping and third-party logistics (“3PL”) integrations to also manage the end-to-end post-checkout (fulfillment and delivery) journey. Unlike traditional black box logistics solutions, PDQ offers modifiable settings that allow merchants to control shipping premiums, fulfillment priority, and tap into hundreds of carrier options to optimize delivery times and cost structures based on customer data. This approach creates checkout experiences that are transparent, adaptable to individual customer needs, and optimal for the merchant.

For example, merchants can dynamically ingest customer telemetry to recognize “low purchase intent” and can automatically personalize the checkout experience to convert the sale with accelerated delivery timelines, reduced shipping costs, free gifts, or even a countdown timer to instill urgency. When a completed purchase is expected to arrive late, PDQ’s rule-based engine can automatically send the customer a discount code for their next purchase, review millions of historical shipment data points to provide an accurate estimated time of arrival (often better than carriers themselves), and proactively initiate customer communication to ensure that the customer experience remains best-in-class without any human involvement (cost savings + increase in LTV). Accomplishing this level of optimization in real-time across thousands of customers, millions of data points, and billions of permutations is impossible without a platform like PDQ.

PeakSpan’s thesis for PDQ falls squarely into our ecommerce logistics thesis published in 2021, What Billy Beane Can Teach Us About Ecommerce Logistics, where we outline the need for brands to adopt best-in-breed point solutions to co-exist with Amazon (see “center field” and “right field” sections). Amazon has raised the bar on what consumer checkout and shipping experience should look like, training hundreds of millions of consumers to expect immense flexibility, fluid checkout, and delivery promises that are met. Amazon is a fine-tuned and highly profitable marketplace with logistics capabilities as the crown jewel on the back-end. Similarly, PDQ is a unique and powerful blend of front-end ecommerce checkout personalization and automated back-end post purchase orchestration that allows D2C brands to deliver on “Amazon” expectations.

PDQ’s unique combination of ecommerce personalization and logistics optimization positions it as a highly differentiated solution in the market. Incumbent website and ecommerce personalization platforms will struggle to compete with PDQ’s logistics capabilities, while traditional logistics and post-purchase experience solutions, would face an uphill battle given the complexity and depth required to operate in the ecommerce personalization space (data collection, personalization engine, segmentation / testing, website optimization, etc.). By bridging this gap, PDQ enables D2C brands to offer personalized checkout experience, powered by optimized logistics decisioning on the back-end, resulting in enhanced customer satisfaction, operational efficiency, and improved order profitability.

In summary, we see PDQ as attacking a high-potential yet largely untouched segment of the ecommerce journey, the checkout experience: The importance of a solution like PDQ is further supported by the following trends:

1. 73% of retail ecommerce journeys end on the checkout interface

2. 60% of online shoppers abandon their carts due to unforeseen shipping and handling costs

3. 48% of customers will add more items to their cart to qualify for free shipping

4. 66% of shoppers expect a free shipping option on all online orders

5. 24% will abandon carts when no delivery estimate is provided

6. Retailers’ ecommerce logistics spend will continue to increase in coming years, with 99% of businesses surveyed indicating plans to offer same-day delivery by 2025

7. The average online retailer spends 70% of AOV on order fulfillment, illuminating the potential for both shipping costs and revenues to be optimized

8. By 2025, D2C sales are projected to account for 30% of all food and beverage sales in the US (a top focus segment for PDQ)

9. D2C food and beverage sales have an average conversion rate of 5.8%, over double the general ecommerce average

10. D2C food and beverage companies see acute customer loyalty, with some subsectors’ customers returning to brands 48% of the time

What’s next for PDQ?

1. With more capital and resources now available to the business, we look forward to continuing PDQ’s tradition of innovation surrounding its cutting-edge checkout and shipping personalization engine. We see ample opportunity to build out product capabilities for brands to operate with similar capabilities to the likes of Amazon when it comes to personalized checkout experiences.

2. We plan to double and triple down on customer success and support while deepening PDQ’s data and intelligence moats.

3. On the back of helpful customer feedback, there are several logical product extensions in the works which we are excited to share more about in 2025.

4. The capital will also be leveraged to bring PDQ into several headless e-commerce ecosystems (Salesforce, Commerce Tools, Magento, etc.) while continuing the Company’s continued commitment to best-in-class service to the Shopify ecosystem.

5. Overall, we plan to bring the joy and impact of PrettyDamnQuick to more e-commerce brands!

If you are a brand, partner, or e-commerce professional interested in learning more, please reach out to Jack Freeman (Partner, PeakSpan Capital), or Scott Varner (VP Revenue, PDQ). We’d love to chat.

Suffice to say, we are pretty damn excited to be working with the PDQ team!