Software PE Pulse: Retail SaaS (Q2 2025)
Every few weeks months, I try to publish a round-up of recent M&A transactions from a particular software sub-sector. I’m seeing a resurgence in retail software as consumers emphasize omnichannel interaction. Retailers need to respond with modern, flexible solutions that let the customer get their items where they want, when they want.
Feel free to reach out if it’d be relevant to discuss any of them.
365 Retail Markets acquires Cantaloupe for $848m (Jun 2025)
Category: Self-Service Retail
Type: Transformational Add-on
365 Retail Markets is a large retail software and hardware business that helps foodservice operators run efficient retail operations. 365 Retail Markets is particularly adept at unattended retail: this could be vending machines, cashierless C-stores (like airport ones) or “micro-markets” in break rooms. 365 Retail Markets powers all the hardware, software, and payments for these unattended retail operations to run 24/7 and track inventory.
365 Retail Markets was founded in 2008 in Troy, MI (a Detroit suburb). They raised a few rounds of venture capital, then took an investment from McCarthy Capital in 2016 and were bought by Providence Equity Partners in late 2020 (the current owner). Providence has been extremely active in M&A, helping 365 Retail Markets close 9 acquisitions in four years. These have ranged from expanding their footprint and product to the catering market (Spoonfed) to expanding into senior living food service (FullCount), and adding menu and kitchen management capabilities (Kafoodle). Most acquisitions were small, except for the latest.
Cantaloupe is also in the self-service retail market. Their vertically integrated software+payments platform gives operators a centralized dashboard to view product-level sales, inventory levels, cash & cashless reconciliation, pricing & promotions, and more across all retail types (vending machines, micro-markets, smart coolers, etc.). They also provide hardware like card readers and smart kiosks, similar to 365 Retail Markets.
This acquisition is transformative for both companies and acts more like two halves coming together rather than one big company acquiring a small one. 365 Retail Markets has the leading front-end kiosks and Cantaloupe has the payments; integrating them means 365 Retail can internalize the interchange fees instead of paying a third party. It also unifies the kiosk and telemetry data - knowing what’s scanned and sold, and if the SKU is out of stock, misplaced, expired, or still there (affecting restocking route planning).
Greater Sum Ventures acquires MyVenue (May 2025)
Category: Verticalized Point-of-Sale (POS)
Type: PE Platform
Greater Sum Ventures (GSV) is a growth equity investing firm from Ross Croley’s family office. Croley previously founded and led Community Brands, Ministry Brands, and other successful vertical SaaS companies. GSV was founded in 2016 and has invested in dozens of software companies.
They invested a majority stake in Australia-based MyVenue, a retail software platform for stadiums and hospitality. Their core platform is an easy-to-use point-of-sale software that can be dropped onto any hardware (tablet, kiosk, handheld) that enables hospitality staff to start selling quickly. This is useful for large venues where customers buy food and drink in several formats - from fixed restaurants to roaming beer hawkers in stadium aisles. The main differentiator is that MyVenue is cloud-first (while legacy POS providers are on-prem), so all endpoints (fixed concessions, mobile carts, self-serve kiosks) feed into the same system, and can flex up and down as volume changes (think half-time rush at sports games).
Vehlo acquires Dealer Pay (May 2025)
Category: Verticalized Payments
Type: Add-On
Vehlo is a technology company providing software and payment solutions to the auto repair industry (both dealership service lanes and independent repair shops). It’s an all-in-one vertical SaaS solution that includes shop management software, payment processing, customer communication, and digital vehicle inspections (mobile tools to review mechanic procedures and document the vehicle). Vehlo took outside capital in 2020 from Greater Sum Ventures and PSG, joined by HarbourVest, Lightyear, and Parkwood in 2022, representing the current ownership structure.
Vehlo purchased Dealer Pay, another automotive technology company. Dealer Pay specializes in payment processing, point-of-sale (POS) and related software. They let dealers accept various payments through various methods, all integrated into a single platform. For example, after servicing your car at your dealership, instead of waiting in line to pay, you receive a text to your invoice to pay from your phone with your preferred method.
This is Vehlo’s fifth acquisition since 2022, each expanding their product suite.
SPINS acquires Lucky Labs (May 2025)
Category: Retail Activation
Type: Add-on
SPINS is a retail data and analytics platform specifically focused on natural and independent grocers. They aggregate data from thousands of grocery stores (particularly natural, organic, and specialty grocery stores), combine it with other data like product attributes, and make it accessible to brands and grocers. An example: say you’re a new keto-friendly protein bar. You could use SPINS to understand which grocers have a lot of “no sugar added” protein bars vs ones that don’t. You could also benchmark your sales velocity against other top brands or see which claims are selling fastest (“plant-based” vs “gluten-free”) to adjust your marketing. SPINS has been owned by large private equity firms since 2016 and the majority shareholder is Warburg Pincus.
Lucky Labs, meanwhile, provides software tools to help brands connect online discovery with in-store purchases. This allows them to tell shoppers, “you can buy this item at a nearby retailer, right now.” Previously, brands did have a screen to see retail locations offering the product, but it was static. Lucky Labs did the hard work of integrating with multiple retailers to show shoppers real-time inventory data -- preventing situations where a customer wants an item, goes to a store because the brand said it was available, but it’s out of stock. They also provide tracking so brands can understand what online marketing leads to in-store visits or purchases, making it clear when campaigns work (previously impossible as customer data was lost once they left the site).
SPINS bought them to help their customers close the loop. SPINS already had rich in-store product-level velocity data. Now they can extend that journey back to online discovery, allowing their customers to see data from lead generation to in-store conversion.
YOOBIC acquires SimpliField (Apr 2025)
Category: Field Sales
Type: Add-On
YOOBIC is a London-based retail tech company focused on retail associate communications, training, and task execution. You can think of their product as something like Slack (comms), Trello (workflow/tasks), and Duolingo (gamified training) all-in-one, built for retail associates on the floor (not at a desk). Here are a few use cases:
A fashion retailer’s headquarters wants a retail display changed because a different item is selling better. The new display details are sent to the retail associate for each store. The associate then makes the changes and submits a picture, which is approved by AI to comply with HQ (and the dashboard turns green).
In a fast food restaurant, a new retail associate onboards to YOOBIC and receives food safety education modules. Daily quizzes unlock new modules if they answer enough questions correctly.
A regional manager will visit 3 stores today to check compliance with food safety protocols, promotional setups, and cleanliness standards. They will walk through the aisles and tick boxes for compliance or take photos for needed changes. This syncs to the system and generates a task list for store employees based on the feedback.
YOOBIC was founded in 2014, has raised several rounds of venture capital funding, the latest being a $50m Series C in late 2021.
They purchased SimpliField, founded in 2014 in Paris, which raised about $16m in venture rounds. Their product is similar to YOOBIC: helping retail operations teams manage tasks, communications, and compliance. The acquisition rationale seemed twofold: YOOBIC was enterprise-focused while SimpliField was mid-market-focused, allowing quick entry into a simpler, higher-velocity customer base. The second is product expansion. While SimpliField and YOOBIC overlapped, SimpliField has additional analytics and reporting features that would enhance YOOBIC. SimpliField let ops managers pull in external data (sales, NPS, etc.) into the app, and slide and dice it without exporting to a business intelligence (BI) tool. This let decision-makers create dashboards and make decisions faster.