Ken Pilot

Podcast Host: THE RETAIL PILOT - Leaders & Legends/Tech Talk, CEO, Board Member, Investor, Advisor

📍 New York City Metropolitan Area, United States🔄 Updated September 2026💼 18 investments📅 10 years investing🗓 Last invested Aug 2026
VC🌍 United StatesInvested this quarter
18
Total investments
3
Early stage
8
Mid stage
1
Late stage
10y
Years active

Portfolio

14 investments · sorted by recency
All investments
Early stage
Mid stage
Late stage
Investor
Nov 2025
Using Gen AI, Kahoona enables hyper-personalization in a cookieless world, allowing brands and online retailers to turn the 96% of website visitors who remain unidentified into high intent buyers. After a few moments of user interaction, Kahoona’s AI predicts a user’s purchase probability, pricing level, demographics and other metrics previously obscured. Kahoona unlocks the AI predictive approach to hyper-personalization for marketing, on-site personalization, retail media, CDP and analytics. Kahoona is the most intuitive way for every brand to get real-time customer visibility and unlock their full potential.
Investor
Sep 2025
At our core is CommerceGPT—a purpose-built large language model platform that simulates millions of shopping journeys and learns from product, behavioral, and synthetic data to deliver real-time, context-aware results. Cimulate’s contextual discovery engine and new MCP Server unlock intelligent, high-conversion interactions across search, browse, recommendations, and conversational commerce—both on-site and across third-party answer engines like ChatGPT and Perplexity. Retailers like Tilly’s, PACSUN, and West Marine use Cimulate to solve the search problem, future-proof their stack, and lead in the era of agentic commerce. Subscribe for insights, demos, and success stories on the future of contextual commerce.
Investor and advisor
Jun 2025
⚡ About Reflex The best retail experiences feel effortless. Behind every interaction is a team that shows up, knows the brand, and makes the customer feel seen. Reflex builds the infrastructure that makes that possible at scale. A living, learning workforce platform that gets more tailored to your brand with every shift. We dont just fill gaps. We protect the customer experience. 👷 For Workers Reflex puts you in rooms where that matters. Find shifts with brands that fit your style, close to home, on your schedule. Every shift you work builds your reputation. Every endorsement makes your next opportunity better. 🛍 For Retailers Every empty shift is a customer who didnt get helped. Reflex makes sure that never happens. On-demand associates, available when you need them for callouts, no-shows, peak seasons, and new store openings. Reflex gets smarter over time. Every shift, every endorsement, every interaction trains future matches. Over time, the Reflexers arriving at your door know your brand voice, your customer, your stores. The future of retail runs on Reflex. https://www.workreflex.com/
mid stageRetail
Investor
Apr 2025
Supercharge e-commerce sales by matching your products to the plans & passions that your customers’ purchases revolve around.
mid stageRetail
Investor/advisor
Apr 2024
FlexFactor is the first AI-powered decline-decisioning engine that identifies, intercepts, and reverses false payment declines in real time – preventing legitimate transactions from ever failing at checkout. The result: more revenue, fewer lost sales, new customers captured, higher LTV, stronger brand reputation, and reduced CAC waste. Powering both one-time purchases and subscriptions, we have reinvented payment decline recovery.
Strategic Advisor/investor
Mar 2024
Increase revenue and speed-to-market with our industry-defining AI design software. Our software enables fashion brands and retailers to understand consumer demand and create unique designs that are in high demand with high purchase likelihood, in minutes, not months. By translating these insights into customized, inclusive marketing campaigns and virtual photoshoots, Raspberry AI empowers brands to authentically connect with diverse audiences—driving higher customer engagement and accelerating sales growth. We bring the best industry-leading AI analytics and generative AI capabilities to fashion product development. Join some of the top 10 global fashion brands using our software to turbocharge the design and merchandising processes. Boston Proper, Gruppo Teddy, Li & Fung, MCM Worldwide and Under Armour are among the leading fashion companies using Raspberry AI to streamline workflows and accelerate product development. Reach out to us at raspberry.ai for more information.
Investor/Advisor
Feb 2023
Your customers look to your brand for guidance. They also spend 3x more when given this guidance in a complete outfit, furniture set, or beauty look. But manual content creation can only cover a small portion of the catalog, leaving revenue on the table. More guidance = more revenue. Before, you had to choose between quality content and scale. Not anymore. FindMine automates and scales content creation so that 95% of products come with guidance on how to Complete the Look. Our system creates Looks that are indistinguishable from ones handcrafted by a merchant. Scale AND respect your brands unique DNA while saving internal teams 99% of their time. Our Complete the Look product shows shoppers how to use each product across e-commerce, email, marketing channels, and in store. As a result FindMine increases e-commerce revenues by 3-10% while creating looks that scale. FindMine serves over 2B looks annually. L2 even cited our Complete the Look as a reason for adidas​ "Genius"​ and Perry Ellis CEO hails "Innovative solutions like FindMine are fundamental to the execution of our customer engagement strategy."​ FindMine is a 2018 Gartner “Cool Vendor”. Having a strong BRANDPOVSCORE™ can explain why your shoppers seek your expertise as an authority on style. Rather than basing your customer’s experience on generic style trends and “wisdom of the crowds” that may damage your brand, it is vital to preserve your brand’s vision throughout the entire shopping journey. Learn more about the importance on providing your brand’s expertise in our research.
Investor/advisor
Apr 2022
Were on a mission to help retailers navigate the complex, competitive and ever-changing retail landscape. Toolio is a cloud-based Merchandising Platform that automates critical workflows, provides real-time insights, and enables remote collaboration, empowering retailers to make faster, data-driven decisions about their most important (and expensive) asset—inventory. Toolio is a global operation with headquarters in NYC and offices in Istanbul, built by an ex-Walmart team of second-time entrepreneurs and backed by top VCs and apparel industry executives. Hop on the rocket ship and learn how Toolio can help your team navigate the future by visiting toolio.com.
Investor/Operating Partner
Apr 2022
Hi! Were Firework. Firework is an ecommerce tech startup that helps brands create & host interactive, shoppable, one-to-one, and short video experiences on their websites. Follow us to learn about developments in ecommerce, tech, and marketing.
Seed Investor/Advisor
Jun 2021
ReUpp is your all in one conversion, retention & sustainability tool. We give customers the opportunity to opt-in to Reupp we give them a buy-back guarantee on that purchase.
Advisor/Investor
Dec 2019
Deep North is Analytics and AI for the physical world. Its end-to-end software solution combines artificial intelligence with computer vision to help retailers and businesses digitize and analyze behavioral metrics in the physical world, and gives them tools to act upon these insights. Deep North lets shopping malls, brick-and-mortar retail stores and transportation hubs reclaim consumer traffic from the digital world to create better customer experiences. The company provides commercial environments with a unique combination of artificial intelligence-based analytical technologies and visual analytics integrated with deep learning algorithms. Deep North gives retailers the ability to assess, interpret and predict consumer behavior in their commercial, physical space. Deep North is developed to govern and preserve the integrity of each and every individual by the highest possible standards of anonymization.
Investor/Advisor
Jul 2019
fabric is the headless commerce platform purpose-built for growth. Customers like GNC and The Honest Company trust fabric for its open and modular design, allowing them to be live in weeks without having to replatform. fabric is a force multiplier on retailers’ existing technology investments proven to grow digital revenue by up to 3x.
Advisor/Investor
Jun 2017
Burrow is not a normal furniture company. Normal was never good enough. Frustrated by compromises between quality, affordability, and convenience, Burrow is taking a new approach. With a focus on innovative, modular designs, ease of assembly, and fast shipping, Burrow is on a mission to solve the biggest problems in furniture. Burrow has joined Havenly Brands. For updates about Burrow, including job openings and the latest company news, please visit: havenlybrands.com
Investor/Advisor
Dec 2016
RADAR is a platform that combines RFID and computer vision to automate and augment retail store processes. Our technology offers unprecedented speed and location accuracy, which allows stores to: 1) Manage inventory efficiently, through automated inventory counts, improved in-store replenishment and instantaneous customer stock checks 2) Measure all customer-product interactions, giving physical stores the same insight into consumer behavior and product performance as online stores. 3) Eliminate checkout lines altogether through our autonomous checkout tool.
mid stageRetail
Experience · 28 entries
All (28)
Investments (18)
Founder (3)
Board (3)
2026
Board Member
Aug 2026
Steven Madden, Ltd. is globally recognized as a leading company in the fashion industry. What began as a modest $1100 investment in 1990 has developed into one of the most iconic brands in footwear. From a factory in Queens, NY, Steve Madden has revolutionized the shoe industry, merging years of experience with unique and creative designs. Inspired by rock and roll and his NY roots, Steve’s vision to provide on-trend women and men with an outlet to express their individuality is innovative, daring, and inspiring. Steve’s innate understanding of trends and unparalleled willpower have resulted in millions of customers worldwide and propelled his designs to the forefront of fashion. In addition to marketing products under its own brands including Steve Madden®, Kurt Geiger London®, Dolce Vita®, Betsey Johnson®, Carvela®, Blondo® and ATM®, Steve Madden licenses footwear, handbags and other accessory categories for the Anne Klein® brand. In addition, Steve Madden designs and sources products under private label brand names for various retailers. Steve Madden’s wholesale distribution includes department stores, mass merchants, off-price retailers, shoe chains, online retailers, national chains, specialty retailers and independent stores. Steve Madden also directly operates brick-and-mortar retail stores and e-commerce websites. In addition, Steve Madden licenses certain of its brands to third parties for the marketing and sale of certain products in the apparel, accessory, and home categories. With an emphasis on retail, wholesale, licensing and international business, theres a constant need for new ideas and versatility. Our environment is extremely fast paced and requires associates to maintain a balance of energy and professionalism. Steve Madden is about fashion-forward product and great people. Our employees are energized, intelligent and passionate about our business and committed to providing excellent customer service.
2025
Investor
Nov 2025
Using Gen AI, Kahoona enables hyper-personalization in a cookieless world, allowing brands and online retailers to turn the 96% of website visitors who remain unidentified into high intent buyers. After a few moments of user interaction, Kahoona’s AI predicts a user’s purchase probability, pricing level, demographics and other metrics previously obscured. Kahoona unlocks the AI predictive approach to hyper-personalization for marketing, on-site personalization, retail media, CDP and analytics. Kahoona is the most intuitive way for every brand to get real-time customer visibility and unlock their full potential.
Investor
Sep 2025
At our core is CommerceGPT—a purpose-built large language model platform that simulates millions of shopping journeys and learns from product, behavioral, and synthetic data to deliver real-time, context-aware results. Cimulate’s contextual discovery engine and new MCP Server unlock intelligent, high-conversion interactions across search, browse, recommendations, and conversational commerce—both on-site and across third-party answer engines like ChatGPT and Perplexity. Retailers like Tilly’s, PACSUN, and West Marine use Cimulate to solve the search problem, future-proof their stack, and lead in the era of agentic commerce. Subscribe for insights, demos, and success stories on the future of contextual commerce.
Investor and advisor
Jun 2025
⚡ About Reflex The best retail experiences feel effortless. Behind every interaction is a team that shows up, knows the brand, and makes the customer feel seen. Reflex builds the infrastructure that makes that possible at scale. A living, learning workforce platform that gets more tailored to your brand with every shift. We dont just fill gaps. We protect the customer experience. 👷 For Workers Reflex puts you in rooms where that matters. Find shifts with brands that fit your style, close to home, on your schedule. Every shift you work builds your reputation. Every endorsement makes your next opportunity better. 🛍 For Retailers Every empty shift is a customer who didnt get helped. Reflex makes sure that never happens. On-demand associates, available when you need them for callouts, no-shows, peak seasons, and new store openings. Reflex gets smarter over time. Every shift, every endorsement, every interaction trains future matches. Over time, the Reflexers arriving at your door know your brand voice, your customer, your stores. The future of retail runs on Reflex. https://www.workreflex.com/
mid stageRetail
Investor
Apr 2025
Supercharge e-commerce sales by matching your products to the plans & passions that your customers’ purchases revolve around.
mid stageRetail
Show all 28 entries ↓
Investment activity
2016–2026 · 18 investments
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