Make Critical Decisions Now for When Your Business Takes Off Later

The following article was written by CJ Przybyl, associate adjunct professor of entrepreneurship, entrepreneur-in-residence, and cofounder and CEO of Reserv, and originally published in Crain’s Chicago Business on October 21, 2024. Read the original article.


Winning your first big account is an exciting moment for an entrepreneur. It’s also a high-pressure turning point, where you have to convert the sales win into a revenue-generating account.

Early on, your infrastructure can make or break this moment.

At my latest startup, Reserv, we grew from 17 employees to 250 in the past year. This was made relatively painless by a few early, critical decisions: choosing software as a service infrastructure, HR, IT and finance vendors whose approach to building products aligned with our values of working fast while staying lean.

My goal is to help you be prepared: You can’t control when the stars align, but you can control being able to seize the moment when it comes.

The groundwork for landing the client

Our first step to a quick launch was building out the most modern infrastructure for, in our case, a claims processing company. We purchased software as a service, or SaaS, subscriptions to the Snapsheet claim system, Vitesse payment platform and Thoropass for items like System and Organization Controls compliance. These names may not be relevant to you, but with our lightweight engineering team and this cadre of modern tools, we were able to launch a scalable service quickly — in less than three months — in the U.S. and U.K. that already eclipsed the industry’s existing capability. Every industry has SaaS tools that are attempting to gain scale with incumbents that are ripe for use by the next new service startup looking to scale quickly. Use them.

An impossible task during our first pivotal moment

After configuring our operational infrastructure and then landing our first big client, we had to find, hire, train, equip and license 75 people in 60 days. We had zero IT or HR professionals in the organization.

That’s a task of Everest proportions. But our team was prepared. Early in the company’s life, one of our founding employees had reached out to an alum of the startup accelerator Y Combinator to ask for advice on how one person could do the job of 10 for the entire back office. His peer floated Rippling, a workforce management platform that we learned was designed to provide massive operational leverage to lean teams.

When the melt-up moment came, Rippling enabled Reserv to automate payroll, hardware and software provisioning, licensing, hiring, onboarding, reams of documentation and benefits with one employee — Matthew Lu — all on top of his primary day-to-day responsibilities. Rippling was critical to our success, but there are also other services available. Again, don’t be afraid to use the tools that are out there.

Three generalized takeaways from our experience

First, be thoughtful about systems that seem boring. Reserv was intentional about infrastructure. We didn’t know when we’d land a big win, but we knew that when we did, our infrastructure had to be ready to work 10 times faster overnight. So, don’t sleepwalk through this decision.

Second, vendors that share a commitment to running lean are the ones that can help you scale. Matthew told me, “Rippling runs globally on Rippling with a hyper-lean team.” If Rippling runs lean on their own platform, then Rippling understands what a lean operator needs. If you find value alignment with your vendor, you’ve found your scale enabler.

Third, everyone worries about downside scenarios, but you must also worry about upside scenarios. “What if the dog catches the car?” Ask: What critical infrastructure needs to scale up alongside you when the big moment comes

Every entrepreneur wants their business to be successful. If you take the time to think through your back-end infrastructure before your moment comes, you will be positioned to truly take your business to the next level.

This site uses cookies and other tracking technologies to assist with navigation and your ability to provide feedback, analyze your use of products and services, assist with our promotional and marketing efforts.

Accept