How to Go From Startup Founders to a Growing Team

My co-founder Andrew and I built Canny, a SaaS tool to help businesses collect and manage customer feedback and build their product roadmap, from the ground up. 

Canny is 100% bootstrapped—we haven’t taken any outside funding. We’re profitable, and we just cracked $800K in annual recurring revenue earlier this year. We’re now a team of seven (and growing). 

However, for a long time, Canny was a scrappy team of two.

Here’s how we got started, and our lessons learned from growing a bootstrapped company. 

How we got started as entrepreneurs

Andrew and I met while I was an intern at Facebook. During that time, we began to work on a tool called Product Pains (which would eventually become Canny) together. 

It started as my thesis project — a tool for users to give feedback about different products. We felt as users that companies rarely cared about what we had to say. We knew there had to be a solution to this.

While I finished school, Andrew worked on Product Pains as a side project. Eventually, we both quit our full-time jobs to build and launch Product Pains, which would soon evolve into Canny. 

What we’ve learned from scaling Canny and growing our team

It’s challenging enough to start a business. But, once you’re past those early days, growing a business brings entirely different challenges. 

We’re a SaaS company, so depending on what kind of business you run, your situation might be a little different. If you’re a first-time founder, here’s our advice for scaling your team effectively. 

1. Focus on matching skill sets and teamwork 

Having compatibility on your team is essential. From the very beginning, it’s important to make sure you and your founding team work well together. 

Before Andrew and I started Canny, we’d already worked together on a number of smaller projects. At one point, we even participated in a hackathon where we won $45,000. It was pretty clear we worked together well.

This was really important when it came to actually starting a business. We knew we made a good team. 

We also knew, as an engineer and designer pairing, we could build a software product without hiring for a while. This made it possible for us to build Canny without having to bring on other people. 

Our skill sets were complementary—and this was a huge advantage. It’s a lot easier to get started with a small team if you and your co-founder(s) have skill sets that complement each other, rather than only overlapping skills. 

Takeaways: 

• Pick co-founders that you know you work well with. If you can test out working together first, that’s ideal. 
• The more your skills complement each other, the easier it will be to build your business in the beginning before you have a team. 

2. Do a lot with a little

As a startup, you usually can’t afford a large team at the beginning. In the beginning, it’s important to focus on sustainable growth while keeping costs low. 

So to start, we focused on building the product. Plus, we couldn’t afford to hire—so in some ways, this made the decision easy.

We also knew we didn’t want venture capital funding. Many startups fundraise to scale their teams right away. In exchange, you give away ownership. We knew we didn’t want to go that route. The “growth at all costs” mindset didn’t sound appealing; we wanted to build a profitable, sustainable company for ourselves and for our customers. 

The limitation of not being able to pay anyone ended up being an advantage. We had to be patient. And we knew that once we could afford to hire, it would mean the business was doing well. 

Takeaways: 

• You might not be able to hire right away. This isn’t necessarily a bad thing. It’s easier to be all-in when you don’t have to worry about paying a team as well as yourself. 
• Be scrappy in the beginning—especially if you’re bootstrapped. There is probably a lot you can do before you need to think about hiring. Focus on your strengths.
• If you can’t afford to hire after you’ve been up and running for a bit, it might be time to reassess. Your idea might not be as profitable as you’d initially thought. 

3. Build a team starting with high-impact areas

Going from founders-only to a team is a big step—you can’t be on the fence about the people you bring on. When you’re a new startup with a small team, you need to be picky. 

When we started thinking about expanding our team, the first step was figuring out which areas would have the most impact. We asked ourselves: 

• What role will help us grow the most?
• Which tasks are taking up a lot of our time? 
• What type of work are we worst at or we least enjoy doing? 

We love doing support and talking to our customers. However, handling it all ourselves was incredibly distracting because of how sporadic the requests were. So, for our first hire, we focused on finding an expert in customer success.

Andrew and I aren’t marketers. We knew that for Canny to grow, we needed to focus on marketing. So, we hired for marketing.

That said, we also aren’t experts in sales. But, we decided that a sales hire could come later, since we could (for the time being) handle demos ourselves, and we were still in the process of building our sales funnel. We wanted to focus on the roles that would have the biggest impact in the beginning. 

We knew it would be crucial to approach hiring very carefully. We’re 100% remote, so making sure we all work well together and communicate well is huge. We’ve written about this often on the Canny blog because it matters a lot to us that we bring on people who are a good fit for the team. 

Takeaways:

• Your first non-founder team members should fill roles that will have a huge impact. What roles would have the biggest impact on your ability to keep growing? 
• What are you worst at? What work do you hate doing? Think about these areas for first hires as well. 
• Be selective. Vet all candidates very thoroughly—both their skills and how they’ll work as part of the team. Don’t be afraid to give test projects or trial periods. 

4. Trust who you give ownership of your “baby”

One of the pros of being founders-only is that you own and oversee everything. 

But, that’s also a huge challenge. You own everything. You wear multiple hats, and this can get overwhelming. Plus, you’re probably not an expert at everything you’re doing. 

That said, giving away responsibility can be scary. You’ve built a company, and you don’t want to give away ownership to just anyone. 

In addition to hiring carefully, hire experts. For early hires, more “junior” team members aren’t usually a great choice. 

The more your new team members own their roles, the better. Look for people who can take ownership of their respective area and run with it. Work with them to set goals, and make sure they’re accountable for meeting those goals. 

The less oversight you have to maintain, the better. It’ll free up your time and energy, and you’ll be able to trust that your “baby” is in good hands. 

Takeaways: 

• Hire experts who can own their respective roles. If you trust their skills and decision-making, it’ll feel good to hand over the reins. 
• It’s not just about skill set. Make sure your new team members can take ownership of their respective space. 
• Don’t micromanage. Instead, set goals and hold people accountable to hitting those goals.

5. Embrace the role of “manager”

One of the biggest challenges of growing a team? Becoming a manager. 

If you’ve been heads-down building product, it can feel quite jarring to suddenly be managing a team. You might not have held this particular type of leadership role before. It was completely new to me.

It’s an overlooked aspect of founding a company. You’re not just growing your business—you’re also responsible for leading a team and helping your employees grow. 

Joining an early-stage startup is a big deal. The people you hire are putting a lot of faith in you and your idea. 

The most important thing we’ve done has been weekly check-ins (AKA 1:1s). These meetings aren’t for reporting on everything they’ve been working on. They’re a chance to talk about any roadblocks, what’s working and what isn’t, how they’re feeling at work, etc. 

As a first-time manager, it’s my goal to make sure my team feels supported— not suffocated. 

Takeaways: 

• Be prepared for the transition from “doer of all things” to “manager” to be a little jarring. That’s okay. It’s important to build management time into your weekly schedule.
• Communicate with your team—hold regular 1:1s, ask how you could be supporting them better. 

To grow, you can’t do everything

In order to scale, you need to build a team. You simply can’t do everything. While it may be daunting, if you remember the following you can establish a successful team:

• Hire slowly and carefully. 
• Keep incredibly open communication. Tell your new team members what’s working and what isn’t. Let them tell you what’s working and what isn’t.
• Hire people you trust, so you don’t have to micromanage them. Hire experts in their fields, who can take ownership with minimal oversight. 
• Accept that you’ll make mistakes. They’re not permanent and they’re not the end of the world. 

Growing pains are inevitable, but they’re positive. We’ve been very conscious that giving away ownership is something we will have to do. And it’s a good thing. Founders can’t carry the whole company on their backs. 

Ultimately, you’ll end up with even more people excited to help you build what you’re building. They’ll be better than you in their respective areas —which is what you need to continue to grow. Growing our team has been one of the most rewarding parts of our journey.