Industry veteran Jonathan Hamblett responds to Cornerstone Information Systems CEO Mat Orrego’s Sept. 12 Op Ed about lessons learned from selling business travel and expense management solutions to small and medium-sized businesses. Hamblett positions himself as a little more hopeful than some readers and shares his lessons as a founding team member at Upside Travel, one of the industry’s most high-profile attempts to corral the SMB market.
Mat’s Op Ed on the challenges of serving small and medium-sized businesses (SMBs) in the travel industry is a great contribution. I appreciate Mat’s expertise and his company’s significant impact on the travel sector. While we share the belief that the industry has yet to crack the SMB market, I think someone out there can — but it has to start with solid product strategy principles.
Industry Verticals Vs. Problem Verticals
In any good product strategy, segmentation is critical. In my opinion, the industry can improve how we think about the travel market. It’s typically based on company revenue, travel spend, or other metrics (there’s no consistent definition).
I propose a taxonomy based on the organization’s priority level of travel management. I see three segments with three different needs (with examples of what a persona could look like):
• Unmanaged Companies (UMCs): No formal travel policy and no need for customizations such as corporate negotiated rates and complex system integrations
• Lightly Managed Companies (LMCs): Basic policy enforcement and some customizations like a few negotiated rates and expense integration
• Highly Managed Companies (HMCs): Complex policy management, multiple point-of-sales, complete corporate negotiated rate program
There’s no doubt that company size correlates to the level of travel management. However, it doesn’t ideally frame their everyday problems. For example, a small engineering firm with a material travel budget may have a much more mature program. Conversely, a large company that prioritizes culture through empowerment may have a more hands-off approach. Segmenting around personas versus industries could allow for better, more scalable solutions.
The Sales Cycle Dilemma Can Be Solved
In my experience, long UMC sales cycles are less about bureaucracy and budget constraints and more likely due to companies prioritizing sales and scale over travel program management. I believe unmanaged company sales cycles could be reduced if companies solve the right problem. Remember that people hire products and services to perform a job.
To do this, companies can utilize frameworks such as Jobs-to-be-Done (JTBD) and conduct in-depth customer interviews to reveal the root causes of their challenges. At that point, companies can design solutions that address fundamental needs common across most industries rather than addressing surface-level symptoms.
In The End, It’s About Product Market Fit
Few companies reach product market fit in the travel industry. I believe new entrants or companies targeting UMCs need robust product strategies to win in the UMC space. They should focus on the right segments and spend considerable time defining the right problem to solve. Doing so can potentially reduce the UMC sales cycle and present opportunities beyond industry verticals.
Thank you, Jonathan, for your thoughtful response. I completely agree that product management plays a huge role in driving adoption, and I’m also a big fan of the JTBD framework for truly understanding user needs. Compelling user experiences and enterprise systems often feel as divided as our political process. On one side, users expect seamless, intuitive interfaces, while enterprises are tied to complex systems and policies. Bridging this gap requires careful product design that simplifies integration while delivering real value — a challenge that, when approached thoughtfully, opens the door to adoption in the SMB market.