

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!
Jack has worked with growth-stage technology businesses his whole career and has partnered with over 25 portfolio companies at PeakSpan. He currently leads PeakSpan’s FinTech and Supply Chain investment themes. Jack was named to GrowthCap’s Top 40 Under 40 Growth Investors List in 2025. Prior to joining PeakSpan, Jack worked at Stackpop, an early-stage startup, where he helped build a SaaS spend management platform that enabled CTOs and IT teams to buy and manage internet infrastructure. After Stackpop was disrupted by AWS, Jack joined Macquarie Capital, where he spent three years executing software M&A and capital markets transactions for technology businesses.
Jack holds a B.A. in Economics from Middlebury College. Prior to Middlebury, he played Division I soccer at Seton Hall University and for the New York Red Bulls U-23 team. Jack lives in Larchmont, NY, with his wife and two dogs, Willow and Leeuwen. Once a year, Jack captains a team in a charity bike ride to the Hamptons to support his brother’s autism program, Quest, where he has raised over $100K. Since retiring from collegiate soccer, Jack has become an avid endurance athlete, completing five of the “Big Six” World Marathon Majors (London remaining), an Ironman, and a 50-mile ultramarathon. He is currently focused on improving his marathon time from 2:32:30 to sub-2:30.
Yaseen joined PeakSpan Capital in 2021 and, over the past decade, has spent his career working on and alongside software companies at pivotal moments in their respective journeys. Before PeakSpan, he was an investment banking Associate at J.P. Morgan, advising software companies on M&A and capital raises. Earlier in his career, he worked as a quantitative analyst building statistical and machine learning models focused on portfolio risk modeling.
Yaseen holds both an M.S. and a B.S. in Quantitative Economics from Cal Poly San Luis Obispo and is a CFA Charterholder. A builder at heart, he is obsessed with the mission of being the partner of choice for growth-stage entrepreneurs and has the privilege of joining exceptional teams as they scale go-to-market, evolve product strategy, and build enduring companies. He lives in California with his wife and pinches himself every day that he gets to be part of such an amazing team and boards.
Mikayla grew up in Chapel Hill, NC. She graduated Phi Beta Kappa from Amherst College with a B.A. in Spanish while also completing pre-med requirements and captaining the varsity soccer team. Before PeakSpan, she worked at a neuroscience research lab at UNC Chapel Hill and at a management consulting firm.
Mikayla joined PeakSpan in 2023 after interning at the firm the prior summer. She started on the GTM Tech, Payments & Fintech, and Supply Chain Tech investing teams and has since moved to supporting PeakSpan's Strategic Development program, where she works closely with portfolio companies on exit preparedness, strategic positioning, and long-term value creation, in addition to Investor Relations. She currently serves as a board observer for Dispatch and Routefusion. In her free time, she enjoys traveling, trying new sports, and listening to anything but country music.
Eavan received her BSE in biomedical engineering with a minor in economics from Duke, where she discovered early on that she wanted to build a career investing in healthcare-related technologies, leading her to her first summer at PeakSpan. During this internship, she quickly realized the B2B SaaS world was vast, ever-evolving, and incredibly exciting. After returning for a second summer and eventually joining full-time in 2024, Eavan has worked across the Digital Health, Supply Chain, and FinTech teams, learning something new every day from the talented people in the network and portfolio companies. She loves working out of the New York office but always appreciates trips to the office out west to see her family in the Bay Area.