LeafLink CTO Zach Silverman on Building Vertical SaaS Companies

This week’s newsletter features a Q&A with LeafLink CTO Zach Silverman. LeafLink is a software platform connecting retailers to brands and manufacturers in the cannabis industry that was founded in 2015 and currently works with more than 10,000 customers in two different countries. Zach offers his advice on building a great engineering team, his experience co-founding a vertical SaaS company, and much more.?

Why do you enjoy working in the B2B space?

Zach: I really like understanding real world problems that unlock real value for people. I get really excited about that. On the B2B side, that's where these kinds of problems live. You also get to go deep into a specific industry and understand its nuances. You get to meet a tremendous amount of people, get to know them, and understand why things are the way they are in the industry so you can reimagine it. As a result, you can build a really defensible business—someone can’t just come along and create a cooler app overnight. From an entrepreneurial standpoint, I think there’s something really powerful about the moats you can build in B2B. You can really put down tracks that change the landscape of an industry.

Do founders already need to have a passion for the industry to build a vertical SaaS company?

The answer is somewhere in between. You don’t have to be gung ho about dentistry, but you do have to be excited about solving dentists’ problems. So maybe you won’t fall in love with the industry overnight, but you should be excited about using your engineering skills to make the industry more efficient and bring benefits to their customers. It’s less about dentistry and more about applying your skills to solve something that will empower other people. It just so happens to be in this particular industry and that’s fine. In the B2B world, you’re giving people back time and money, you’re helping them automate tasks and manage governance and compliance. That puts them in a position where their business is less risky and it enables them to have a higher quality of life.?

Were you nervous when you started LeafLink? How did you address those anxieties??

A lot of the things I’m most nervous about don’t actually come to fruition. That’s not to say you shouldn’t be nervous about them, but the harder you work the luckier you get. My advice is to forge through it and you’ll find your way. You don’t have to do it alone. Raise your hand if you need some support. Bring in a consultant or whatever it may be. But try to at least drive the vision behind it. You’re going to have moments of doubt all the time. There are failures every week. But if you understand where you’re going, if you’re honest about what you know and what you don’t know, if you make sure you’re building a team that compensates for what you don’t know and empowers what you do know, and you’re honest about your ego, it will help compensate for any imposter syndrome or other psychological things that come up while building a company. It’s extremely hard, but the best way to make it easier is to find really amazing hires. To have someone transformative.?

What is the most rewarding part of your job as a founder and CTO?

There are two parts: One is helping to define how an industry is going to operate. The other is the people who you meet along the way. The people who want to apply their amazing skill sets and bring this thing to life. That to me is the essence of what is so powerful and cool about being a founder and an entrepreneur.?

What are the biggest challenges you face as a CTO and how do those change over time?

People are a hard thing to manage as you grow a company—yourself included. How do you scale yourself? How do you make sure you’re doing the right things? How do you make sure you’re enabling people? How do you make sure you’re delegating? Humans are extremely dynamic and the world is constantly changing, so you need to figure out how to keep people engaged and confident in your company. You need to show that you trust them. It takes effort and you need to lean into it.?

How did your role as CTO change as your company grew?

Initially it’s really fighting for product-market fit. You’ve got to really be driving that when it’s just you and a handful of other people. Once you start to bring in more engineers your role is kind of split in two. You’re an individual contributor and visionary for what needs to be done, and you start to take on a management role. Not necessarily formally because most people you hire right out the gate should be pretty independent and not need a lot of oversight. We built that culture up to about 10 people and then the role for me really started to change. We started organizing, breaking up the platform into general domains and started to get some people specialized within the domains. At that point I was less of an individual contributor and more of a highly active manager. After your Series A, it’s really about recruiting and kind of stayed that way for the next two years, but still finding ways to kick out a feature here, squash a bug there. At that point, the role is really all about team building. Once you’ve hired about 50 to 60 people, you start to become a manager of managers and you’ll bring in senior people that can offset whatever you think are your weak areas so you can focus on your strengths.?

How can a company like Fractal help engineers transition to CTOs?

There are a lot of accelerants that Fractal’s program bakes in in terms of best practices and things to avoid. I don’t know how many scars I have that Fractal’s program could have helped me avoid. The models, the financials, everything is worked out in a way that de-risks building a company and makes it worth the premium. I absolutely would pursue it. This is especially true from the engineering side because the truth is that in early stage companies, cofounders really need to come to the table as one unit and show the world what they’re going to bring to it, most notably in terms of fundraising. Not all engineers are built to go out and sell something that doesn’t exist. Fractal’s model is very much “here’s the vision, you don’t have to sell me, and by the way here’s what you need to be successful.” That’s a totally different starting point and can attract talented engineers who are able to realize the vision, but might be less excited about starting something without those guide posts in place.?

Any parting advice for new founders?

Right out of the gate, always try to make the implicit explicit when it comes to your culture and your vision. This isn’t to say that the vision can’t change, but be explicit about it. Don’t just find yourself wandering down a path. If something is floating around and is implied, nail it down, document it, and share it with your team.