The Founder’s Dilemma: Scaling Operations Beyond Solopreneurship

Every founder faces a major conflict in the early days of a business. When you start to gain momentum, there comes a point when you know deep down you need to hire a team to help. However, doing so would require you to slow down the momentum you’ve built and focus on setting up processes and operations—the buzzkill of running a company. 

When you’re a one-person show, “operations” may not even exist. What a larger business might refer to as “operations,” you might simply call action. 

You’re flying by the seat of your pants and operating in chaos. The recipe for the secret sauce only lives inside your head. There’s no time to slow down and set up processes. You know what you’re doing, right?

You can usually lone-wolf your way to a lot of success in the early days of your business—until you can’t. 

What should you do when you’ve outgrown solopreneurship? How do you find the right people, get them the right tools, and set up the right systems to scale your business to the next level? 

Get the Knowledge Out of Your Head

Be honest: Are you operating your business with the mindset of an individual contributor rather than a leader? If so, you will be limited in how much you can grow. The first step is to change your mindset. 

As a leader, you can either remove obstacles on the growth path or you can become the obstacle—and bottleneck growth. 

Know when it’s time to get the f*ck out of the way for the good of your business.

Of course, as founders, we know this is easier said than done. 

The thought of delegating creates anxiety. You want to do things perfectly or not at all. 

You know your business best—if you didn’t, you wouldn’t be where you are today! But you might not know how to hire and onboard. You might not know how to operationalize things. You know you couldn’t do it perfectly, so you delay it much longer than you should. 

Stop aiming for perfection. Perfection is the enemy of progress.

If you want to grow, others need to leverage your expertise. You have to get that knowledge out of your head and into theirs with processes and systems that others can repeat, adopt, and refine.  

My advice: Treat your hiring and operations like a product. You’ll need to iterate to figure out what works through trial and error. It’s important to start today with imperfect versions so that you’ll have it figured out three years from now. By that time, the stakes will probably be much higher anyway. 

Once you’ve made peace with the idea of letting others in the door, you need to find the right people for the job. 

Hire People that Can Operate in Chaos

Developing an effective hiring and onboarding process is an investment in your future business, but it can feel like a thankless chore at first—especially if you rush through or half-ass it. 

Plus, it’s time-consuming to recruit, hire, and onboard! As a founder, you probably have a low tolerance for tasks that aren’t directly generating revenue right now. 

Here’s a cheat code I learned in my early days bootstrapping Close:

Hire the people who can operate in chaos. 

You need to hire the right personalities—people who are okay with imperfect systems. 

People who get excited about your imperfect early-stage or solopreneur system can bring order to it. They can pressure test your operations and sniff out inefficiencies, replacing them with better ways of doing things. 

Look for people who are flexible, creative, and hungry for a challenge. They’re the kind of people who can work on a 5,000-piece puzzle without getting frustrated and flipping the table over.

In other words: You can get out of their way and trust them to get shit done. 

It might sound counterintuitive at first. After all, if you don’t have a ton of experience with operations, shouldn’t you hire someone with a long history of doing it? In my experience, not necessarily. 

A 10-year corporate vet from a large company might not even be able to find the bathroom without a handbook. The people who expect you to have perfect systems often require a lot more hand-holding. 

You want someone who can solve problems without getting you involved. These are the people who will actually help you get time back in your day so you can focus on running the business. 

In the early days of Close, my day-to-day work consisted of cold outreach, sales consulting, creating content to fuel our marketing strategy, overseeing software product development, and a thousand other things. It was chaos! 

But because I hired the people who could complement my chaos with their ability to bring order to our operations, it set us up for long-term stability and growth. Today, Close employs nearly 100 people—with each new hire added to create more momentum.

Once the right people are in place, the next challenge will be to figure out how to offload your knowledge and operationalize your sales.

Crawl, Walk, Run

The first system you create to manage your sales process will fail. It will become the reason you can’t scale. At some point, you’ll need to replace it with something better. 

Like hiring, your sales processes and systems will require multiple iterations before running how they should. Once again, you’ll need to fight the urge to do things perfectly the first time. 

To avoid feeling overwhelmed or stuck in indecision mode, take a “crawl, walk, run” approach to your sales operations:

• “Crawl” = Document your processes to create a foundation for scaling.
• “Walk” =  Find a low- or no-cost, lightweight CRM to establish repeatable processes for your sales efforts (and to work out the kinks). 
• “Run” = Arrive at a more powerful, durable solution that can accelerate revenue growth and provide significant ROI.  

Here’s an example of what a “crawl, walk, run” approach might look like for a small business needing a sales process to scale growth. 

Crawl

You can start with a process scribbled on a whiteboard, a sheet of notebook paper, a Word doc, a cocktail napkin—anything. The goal is to make a first attempt at documenting the founder’s knowledge and secret sauce in writing so the broader team can leverage it. 

That’s it. That’s “crawl.” Simply write the information down. Boom—there’s your first process.

You’d be surprised at how many founders struggle to complete this first step because we’d rather rely on our instincts instead. Just do the damn thing. 

Walk

All the knowledge has been transferred out of your brain, and it’s time to get organized. Now, there are multiple chefs in the kitchen, which means your sales and customer data is likely scattered everywhere. Everyone probably has their own way of doing things. You need to create a single source of truth so everyone can walk in the same direction.  

Move your sales process to a makeshift CRM in Excel or Google Sheets (or if you’re short on time, you can download our free CRM spreadsheet template). 

Seeing your sales pipeline mapped out visually can help you figure out what’s working and what’s not. 

Treat your spreadsheet CRM like a lab where you conduct experiments to refine your sales process. Are you noticing patterns over time? Are there log jams where prospects are getting stuck in your sales cycle? 

Understand that this is still a lightweight process that will only get you so far. You can think of this stage as the minimum viable product (“MVP”) of your sales systems. But a spreadsheet isn’t meant to hold the weight of a growing business forever. 

In time, the cracks will start to show. Your founder-built process will collapse. 

Many founders ignore the problem here because switching to a more formal tech solution seems too painful—but the opportunity costs of not evolving your systems at this critical point can be even more painful. 

Run 

Let’s say you’ve spent a year working with your homemade spreadsheet CRM. You find that 90% of your contacts are cold or dead-end leads from a lack of follow-up. You’re leaving money on the table by letting those opportunities fall through the cracks because you don’t have better systems to automate things. 

You’ve crawled, walked, and now it’s time to run. 

You’re ready to graduate to a real CRM—but you don’t want to spend a lot of money. Here’s a common early operational mistake many founders make that can be painful to undo later. 

You’re unsure what tech option to commit to, so you look for a cheap, entry-level solution just to dip your toes in the water. Maybe you start with a basic, no-frills CRM (like Pipedrive, GoHighLevel, etc.) that will give you the bare bones of a CRM, but it won’t be enough.

Slowly, you discover you need to add a bunch of other tools to compensate:

• Phone call functionality
• Auto dialer and phone menu capabilities
• Call recording and transcription 
• Automatisation des courriels 
• SMS marketing automation

So you duct tape together a SaaS sales stack based on the cheapest options, and create a three-headed Hydra monster sales stack. 

This approach can work at first (especially on a shoestring budget), but it can also backfire. 

You need to know when the processes you spent so much time setting up are getting in the way. You might find that things have become too complicated, customer data is fragmented across multiple tools, and your team is whining about the tech. The solution has become a new, different problem. 

Remember that the point of using tech at this stage is to “run”—the faster, the better. I never want to “walk” if I’m investing in systems that are supposed to help me “run”! 

Don’t fall into the trap of thinking that any tech solution is better than none or that the first one you choose will be the last. If you’ve over-engineered a complicated sales process, you’ll need to pivot, which can be painful but necessary. Never stick with a mistake just because you spent a lot of time making it.  

Back in 2013, when we were still a Silicon Valley sales company called Elastic Sales, we were frustrated that none of the sales tech on the market was accelerating our growth as a small scaling business. We had high expectations and wouldn’t compromise because we knew our future was on the line. So we built our own CRM to do all the things we needed it to do—and it became Close. I’m not saying you need to build your own software from scratch, but find what works for you. 

Keep Evolving as Your Business Grows

I’m biased and think Close is the CRM to choose, but you might find that the best solution for your business is something like HubSpot or Salesforce. The point is to be willing to adapt your systems and processes when you find they’re not working.

Look, I know you probably didn’t become an entrepreneur because you’re passionate about systems—but as you grow, you need to continuously evaluate your sales operations. Watch the metrics, get feedback from your team, and be willing to make changes if necessary. 

How much faster could you grow by investing in the things that speed you up rather than slow you down? When is it time to go through the pain of evolving your systems to achieve your growth goals? Not every founder wants that pain, but they still want the growth to happen anyway. That’s the conflict.

These are tough questions to answer. The solutions are not always obvious and depend on a wide variety of things—from founder personalities to industry type to customer acquisition strategy and more. 

As long as you’re willing to adopt the mindset of constant evolution and iteration, you’ll eventually land on systems that turn your business into a well-oiled machine and fuel your growth for years to come.