Procurement Express

James Kennedy wasn't initially planning to build a procurement software company. He had a struggling online business that wasn't going anywhere, and when he and his wife got pregnant with their son Max in 2016, he realized he couldn't afford to drag his family into a failing venture. Around the same time, his business partner Richard came back from his IT support business in Dublin with an interesting problem: two customers in the same week—UNICEF and Clarence Cosmetics—were looking for the same thing. They didn't need a full ERP system, but they desperately needed purchasing controls. UNICEF needed approval workflows because they were handling public and donation money with reputational risk. Clarence Cosmetics had lost 150,000 euros of stock from a supplier and needed controls to prevent that from happening again. Richard Googled for a solution, couldn't find anything decent, and came to James. They hacked together the first version and named it Rubber Stamp.io, which James admits he hated but thought they probably wouldn't be around long enough for it to matter.

The original customers came through Richard's IT support relationships—a perfect example of finding early traction through existing networks and solving tangible problems. However, as the business grew, James realized the name Rubber Stamp had a perception problem in the US market. Some customers interpreted "rubber stamp" as waving things through without proper scrutiny, which was the opposite of what the product did. Worried about brand confusion and wanting to appear more professional as they scaled, they rebranded to Procurement Express. In hindsight, James suspects this was a mistake—the memorable, clever name probably drove more curiosity and word-of-mouth than the more descriptive but generic name they chose. He notes that competitors like Procureify and Precoro create so much naming confusion that prospects sometimes email saying they've decided to work with Procurement Express, only to later say they're going with a competitor because they couldn't tell the companies apart.

The company eventually stabilized at around 300 customers globally (half in the US, half elsewhere) managing $3 billion in annual spend. James took an angel round from five investors in 2016 but remained otherwise bootstrapped, building to a ~$2M ARR with about 25 team members. The key insight came from years of listening to bootstrapping podcasts, especially Jason Cohen's 2013 MicroConf talk on building a sustainable SaaS business. About three years before this interview, James implemented a radical pricing strategy: annual price increases of 5-10% every September, announced upfront to customers. This wasn't just a revenue optimization play—it solved multiple problems at once. Previously, they hadn't raised prices for years, creating a pricing mess where some customers paid $50/month while new customers paid $300/month. Managing all the different pricing tiers created accounting and operational chaos. When they finally did a big 20% increase, churn spiked. The annual increase strategy flipped the problem: predictable 8% increases surprised no one and mostly churned out the inactive users who weren't getting value anyway. The email subject line became a marketing tool itself: "Our smallest price increase ever and 10 new features we made for you this year." This forced discipline—James would write the annual increase announcement and ask the team: "What are we going to say we've built this year to justify asking customers for more money?" It became a forcing function for product prioritization and continuous improvement.

At $2M ARR with steady, predictable growth, Procurement Express represents the kind of "boring" business that thrives in the MicroConf community—not chasing unicorn valuations or venture scale, but building a profitable, valuable company that solves real problems for real people. James speaks regularly at MicroConf (talks on reducing churn 25% and building a sales factory instead of doing demos) and actively seeks co-marketing partnerships with other SaaS founders selling to CFOs in the same mid-market space. He's confident in the pricing strategy despite being more expensive than some competitors, believing that in mid-market procurement, the actual dollar amount matters far less than the value delivered—time saved, risk eliminated, and better visibility into spending. The philosophy: don't compete on price, compete on value and product quality.