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FreightTech Friday: Learn to Win raises $30M, captures the industry’s attention

CargoSense captures $8M Series A to improve system integrations

This is a rundown of the latest FreightTech news. (Photo: Jim Allen/FreightWaves)

Enterprise training software provider Learn to Win announced on Wednesday an oversubscribed $30 million Series A raise led by the Westly Group with participation from Norwest Venture Partners and PearVC.


The company plans to use the funds to continue building out training platforms for high-pressure work organizations that can’t easily remove employees from everyday work for continuous job training.

Since its founding in 2019, Learn to Win has implemented AI-driven training programs for Novartis, AbbVie, the Los Angeles Rams, University of Michigan football, the U.S. Navy, and the U.S. Air Force, and is the sole source contractor of training technology for Impact Level 6 classified Department of Defense contractors, which process classified information for DOD up to its Secret level.

“Learn to Win is the Palantir of training. It’s very rare for a company to gain this much traction with the DOD and many of the world’s largest corporations. They’re poised to become the modern training solution for the military with a clear path to $100 million ARR in defense alone, and we’re confident they can replicate that success at a greater scale in the commercial sector,” said Danny Cotter, partner at the Westly Group.


The company’s software also caught the attention of industry leader Kevin Nolan, founder of Nolan Transportation Group and venture firm Sope Creek Capital, who invested in Learn to Win after seeing results at the venture firm’s portfolio companies.

“After seeing the success of NTG’s training classes using [Learn to Win], other departments started using it for training and testing freight and industry knowledge. OTR Solutions also uses it not only to train its new staff but to train on new initiatives that the company rolls out internally. … PayHawk is just starting to implement it and we expect to see fast results,” Nolan told FreightWaves.

“Not only did the great product and technology attract Sope Creek to this investment, the management team and culture impressed us the most. From the founders’ grassroots beginning to the incredible talent they bring on, we love the company here at Sope Creek. … We think they can help with training across all industries. Transportation especially needs help, we all know that,” he said.

CargoSense raises $8M in Series A

Data visibility solutions provider CargoSense announced Wednesday that it closed an $8 million Series A round led by Lanza TechVentures with participation from Merck Global Health Innovation, SmoothBrain, The Pallet Alliance and other previous private investors of the company.


CargoSense’s main solution is Visibility OS. The platform integrates a company’s data sources, real-time visibility systems, risk analysis tools, and transportation management system data to contextualize a company’s supply chain and automate operations. This enables supply chain leaders to scale operations quickly with a sophisticated exception management workflow.

With its new capital, CargoSense looks forward to executing its current product roadmap and growing its relationships with industry hardware and software providers to give its current users more integration partners.

“Buyers of visibility data and related supply chain technologies for manufacturers and distributors all share an expectation: that it will reduce workloads for their supply chain teams,” said Richard Kilmer, founder and CEO of CargoSense, in the release. “The reality is frequently the opposite, where there’s a large gap between new technology and their day-to-day operations, and people bridge the gap with additional manual effort and process complexity. CargoSense is on a mission to simplify supply chain operations for any organization, but especially those with significant scale, and we thank our new and existing investors for their confidence in our team and our approach to accomplishing that mission through automation.”

Kilmer went on to explain that a lot of the solutions and automation technology available in warehousing and logistics today have a common issue: They are difficult to configure and integrate to provide a true return on investment. To solve this, CargoSense collaborates with hardware and software vendors to integrate into Visibility OS and give customers a more hands-on approach with their data instead of sourcing everything from the cloud. 

“Having to backhaul data from IIoT devices before any analysis can be performed is a drain on battery life and data plans,” he said.

This approach helps customers make decisions faster, create digital twins of their logistics operations, and accelerate warehouses and logistics providers into a digital era with more control.

“We have long invested in silicon-based technologies that could revolutionize what’s possible with embedded devices and [Industrial Internet of Things]. …CargoSense’s Visibility OS, which targets automating the $10 trillion supply chain and logistics marketplace, paired with our portfolio company’s innovative hardware solutions will more rapidly unlock the business value of pervasive IIoT and its potential to redefine entire industries,” said Michael McNamara of Lanza techVentures, who also announced will join CargoSense’s board.

Brief Bytes

Artur Express announced Tuesday it has partnered with Kodiak Robotics to bring autonomous solutions to its service. According to Artur, it is the first trucking company to operate electric trucks in St. Louis, Missouri, where the company is headquartered. Artur plans to use the autonomous assets on key lanes and specific service models and give drivers a more updated driving experience.


Truckstop.com announced Wednesday it has appointed a new chief financial officer to the team, Joe Pergola. Before joining the Truckstop team, Pergola served as CFO for Connatix and Integral Ad Science. Kendra Tucker, chief executive officer of Truckstop, looks forward to Pergola “delivering results and creating value that will further advance our growth strategy and customers’ success.”


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Grace Sharkey

Grace Sharkey is a professional in the logistics and transportation industry with experience in journalism, digital content creation and decision-making roles in the third-party logistics space. Prior to joining FreightWaves, Grace led a startup brokerage to more than $80 million in revenue, holding roles of increasing responsibility, including director of sales, vice president of business development and chief strategy officer. She is currently a staff writer, podcast producer and SiriusXM radio host for FreightWaves, a leading provider of news, data and analytics for the logistics industry. She holds a bachelor’s degree in international relations from Michigan State University. You can contact her at gsharkey@freightwaves.com.