Issue #41: Founder Mode & Defining Success

We recently hit several milestones (including sailing past 100 customers) and landed some substantial accounts (getting us to over half of the top 10 brokerages). Nearly forty of the top 100 brokers in North America are using Cargado. We have some incredibly important customers who are involved in some incredibly critical supply chains, and that customer count is growing by the day, which means our support needs to grow too.

When I first started lining up meetings with brokers to show them designs of our platform, the first few meetings took place on Zoom. Nearly every meeting, the person on the other end ran into delays joining the meeting, always grumbling about how they use Microsoft Teams. So I set up Teams to start scheduling demo calls with prospective brokers and, all of a sudden, we had a very productive thirty minutes instead of twenty-five after five minutes of frustration that caused the meeting to start cold.

We decided to meet our customers where they were. Getting Teams also enabled us to set up chats with our customers and support them during and after their onboarding in real time. They can ask us anything from how to use the product to when different features are coming to where they should set up an office in Mexico. They get direct access to our team, including Mexico experts like myself.

What I’ve learned from my time in freight and from the past year of building Cargado is that shippers hold a high bar for service when it comes to their logistics providers. Those logistics companies, our customers, then require their providers and vendors to provide a high level of service, something we can do via Teams, Slack, and WhatsApp.

Also, please don’t take this as an endorsement of Teams – I still think Slack is a far superior option with the threading and channel structure, but maybe take this as a bit of advice on how to meet your customers where they are.

The more we invest in the happiness and success of our customers and the carriers in our network, the more our marketplace will grow and the more valuable it becomes to all the participants involved. We envision a very integrated experience in the long run that will only further accelerate those benefits for everyone. This theme sounds familiar because you’ve read about it if you’ve studied marketplaces before.

When you’re building a marketplace business, in particular a vertically integrated one, and when you can move as fast as we’re moving, you just have to go for it and take the market. Marketplaces are most successful if they can harness the flywheel concept that Amazon made famous.

The more activity in a marketplace, the better the experience for everyone. As more logistics companies post in Cargado, carriers see more opportunities that they can win and they increase their engagement. Accelerating the flywheel takes a lot of pushing and nudging. The faster things go, the likelier chances you have of something breaking if you aren’t paying attention.

When you’re a second-time founder, you look at the world differently. I feel fortunate that I can comfortably zoom out from where we are today and try to look around the corner at what’s coming while the rest of the team stays focused on today’s problems. While Forager wasn’t perfect, we went through our fair share of growing pains that feel somewhat similar to what we’re experiencing today. The difference, however, is that our charts aren’t zig zagging up and down, they’re all heading in the right direction. We know there are knobs to turn that will make this business grow faster and we are starting to understand how to adjust those levers.

What I can see coming around the corner is the growing pains we’re going to experience going from 120 customers to 1,000 customers and beyond that. How do you make sure every customer is happy? How do you make sure your customers who move a few loads a week feel just as important as the customers posting freight on a daily basis? These are all questions that need devoted brain power and resources to really nail at scale.

I also love that, for the first time, I feel like we can project growth based on a hiring plan. Drop in X number of sales reps, assuming an appropriate conversion rate, and you can see where the numbers will go. We didn’t have that at Forager either. We were just blindly chasing after shippers to try and get freight and we had to execute on a dozen different items to really nail service for each of those customers.

As I started thinking more about how we’re going to provide that service, it clicked for me that we needed something I had zero experience building – a true customer success function. I’m seeking some of the top success leaders to learn from them and ultimately kick off a search for someone who can roll up their sleeves and keep customer happiness a core part of Cargado’s value proposition.

All of these things are falling into place at this moment where we’re reaching a tipping point. I’ll share a graphic I shared with our team when I told them that we are reaching that moment where Cargado has the potential to accelerate faster than they’ve ever experienced. In that moment you as a founder realize that you need people who have been there before in order to maximize your success at scale.

As you’re sitting there looking at teams or functions where you realize that the requisite experience may not be there today, you stick your own hands into it and dive into the weeds. You do it to help your team and, sure, maybe it feels like micromanagement at first. The reality is that you have a vision for how this thing needs to play out and you know what needs to happen. 

The problem you often run into is that everyone has a level of pride that says that they want to be able to do it themselves. There’s always a tension between the needs of the self and the needs of the greater whole. They want to be able to say that they accomplished solving some incredibly difficult problem and when you hire excellent people you know they could do it. But when a company is growing as quickly as Cargado, you simply don’t have the time to wait to let them do that. And at some point, they realize there’s a much greater opportunity in front of them if they learn to solve that problem faster by working with you, the founder. Deciding which path to pursue just depends on how critical the project is and whether you can afford to let someone learn from failure or learn by watching.

Founder mode doesn’t mean you turn into a maniac and just do whatever you feel like doing because you’re the founder. And it doesn’t mean you stop doing what you owe the business yourself. You still have to lead at a high level but you can get into the weeds and show the team how to get shit done. Great businesses aren’t built by founders fully staying in their lane – they flex into the spots where they’re needed.