Co-Founder and CEO of Help Scout, Nick Francis, shares his insights on how to delegate assignments as the company grows, describes how his position as a CEO changed over the years, and explains how Help Scout manages to provide real human experience through customer support.

Nick Francis is the Co-Founder and CEO of Help Scout, the company behind the popular web-based help desk software. Founded in 2011, Help Scout serves more than 10,000 customers in over 140 countries. 

For as long as he can remember, Nick always learned by doing. Being an entrepreneur gives him the opportunity to get outside his comfort zone daily, learn at a high velocity and make a significant impact.


Why We Started Help Scout

After a few years building websites, in 2011, Nick and his partners, Jared McDaniel and Denny Swindle, decided to start Help Scout:

“When we started help Scout, it was very clear to us that there were several companies that were serving larger businesses. There were several products that were meant to serve the needs of more of an enterprise use case. That’s why they were called help desks. I feel like that whole term was born in the enterprise. It’s a really ugly term, yeah help desk. I don’t know, just doesn’t really have a good ring to it. It doesn’t really sound very human, does it? So when we entered the market, the whole thesis behind why we created Help Scout was to make support more human and helpful as well. So we really wanted to focus on SMB. Small businesses have a … Typically are more customer-centric, right? They typically differentiate from their competition by providing excellent customer service, and an excellent experience that’s meant for a smaller audience.

And so that’s always resonated with me. Like I said, I’ve started a bunch of companies in my life. They’ve all been small businesses and so those are my people. And I feel like if we’re going to build a product, those are the people I know how to build products for. And that just so happened to be that was the space where the market had the most opportunity. So we’ve always focused on small businesses. So that could be where Elementor started, which is one support rep up to several hundred but more than 90, I’d say even 95% of our customers are less than a hundred users. And we’ll have the really fast-growing companies like Slack was a Help Scout customer until they just got way too big and they moved on to Zendesk. And that made total sense.

So there’s a lot of great software companies that we’ve had the opportunity to work with as they sort of went through those early stages. And if you grow beyond Help Scout, it totally makes sense, but we’re not a fit at some level. We really want to be focused on more of the small business use case and to be honest, the small business values, that’s what really makes me excited about working with those customers.”


Stepping Away and Letting Other People Do Their Thing

Recently, Nick took a sabbatical and wrote about it an interesting blog post. But as a CEO holding so many responsibilities, how can he allow himself to take a month off? and how did he prepare for that?

“Well I’ll tell you, you have to make it happen. It’s not something that’s just going to make sense at any given point. It’s always going to be hard. But after almost eight years in the business, I felt two things. One, I felt tired, two, I felt like the business would be better off and the business would learn and progress in ways that I’m unaware of if I were to step away for a month. So it was as much about recharging and sort of rebooting on my end as it was about the company being able to grow and for me to be able to come back and basically rewrite my job description.

I’ve done that three or four times at Help Scout and I felt like it was time for me to change my job description. We’re now more than 90 people that work in 75 cities all over the world and it’s a different company than what it was eight years ago.

And so I just, I felt a bunch of different things sort of tugging on me and saying, “In order for the company to take the next step, I have to learn what it means to step away and let other people really do their thing.” Because frankly, the other people that work at Help Scout are a lot better at all of this stuff than I am. Don’t tell them I said that, but it’s true. We’ve hired a really wonderful team and for me to step away means they’re able to step into leadership and decision making authority that they didn’t have exposure to, which was awesome.

So a lot of things just kind of led to it, and then going through the process, I did spend about three months. I had a big long list of things that I wanted to either finish or hand off before I left. So that was also a really good exercise and sort of taking things off my plate. So day-to-day decisions that I was making, I had to find somebody else to delegate those too, knowing that I was going to be gone for a month. So that was a really healthy exercise and I stepped away. Everything still kept working, everybody learned a lot. So it was a life changing experience for me, to be honest. I think about it every day still.”


I Want to Grow in Scale in Ways That Make Me Deeply Uncomfortable

As a successful startup, Help Scout has experienced rapid growth in recent years, which is a challenge on its own. For Nick, it’s exactly what motivates him in life:

“I absolutely think every company goes through these. Now different individuals may handle it differently. I personally want to grow in scale in ways that make me deeply uncomfortable. That’s why I’m an entrepreneur. I want to learn at an incredibly high velocity. And in order to do that, I feel I have to feel constantly uncomfortable. So for me, it’s really important that I be able to rewrite my job description every couple of years. Otherwise, I may get bored, but there’s other people in the organization that really are at their best and are passionate about a certain stage of a company.

So there are other people that may come and go in your company and add an incredible amount of value, but then they say, ‘You know what? This stage is not really … Like this new job description that you’re asking me to take on, doesn’t feel as good to me. I really liked the job I was doing and I don’t really want to have to adapt.’ And so at that point, they find another company where they can go add that kind of value. So not everybody wants to rewrite their role every couple of years. It’s quite hard, and I have all the respect in the world for that, but for me, I like that. For other people, they just tend to want to work for companies that along a certain stage. And that’s immensely valuable to whatever companies they’re working with as well.”


Acknowledge That You Don't Have All the Information

We asked Nick to compare his work at the beginning of Help Scout, to his work now, with 90 employees — what changed in terms of processes and the way he delegates missions:

“One of the big changes that took me a while to get used to is that I no longer have access to all the information. I almost never have the information. So if I see something that feels off to me or I may not like it, or I may love it, I should just know that I probably don’t have all the information related to how that decision … What went into that decision or whatever, and that doesn’t just apply to the CEO. That applies to everyone in the company. Early on when you’re eight 8, 10, even 25 people, everybody’s pretty much working with all the same information. You know everything that’s going on in the company. When it’s 90 plus people, you do not and you cannot understand everything that’s going on all at once. You will not have all the information.

And so going in with that attitude, before I make a judgment on something, I try to either tell myself, hey, I don’t have all the information and go into a conversation about that, acknowledging it. That’s, been a big key for me. Just acknowledging that I don’t have all the information and the person that did make that decision had a very different context than I did. So it’s really helped me to address any concerns or frustrations that I have in a much more humble way. So that’s been good.”

And yet, there are tasks that Nick keeps close, that he won’t let go of easily:

“I think that would be the vision for the company and specifically the product. You know, we have people at the company now that are really great at casting a vision and a long-term strategy for the business itself. And I’m definitely an input, but that’s not owned by any one person. Whereas the vision for the product is still pretty much what I want to hold on to. That’s a really important thing for me. I still talk with customers every week because it’s really important that I maintain that connection, and can guide the roadmap accordingly.

So for me, it’s just the big vision for where we want to take the product. But you know, you talk to 50 CEOs, you’re probably going to get 50 different answers.”


Providing a Real Human Experience

Towards the end of our interview, we asked Nick to give his outlook on the future of customer service, bots, and AI, and how such a future will affect Help Scout:

“First of all, we bet on small businesses and they typically have different challenges than some really large companies. So there are very large companies like the telecom companies seem to be the most progressive in this respect is doing this omnichannel support where they’re doing Twitter, they’re doing Facebook, they’re doing phone, email, you can find them everywhere.

But if you look at all the studies that are done, you find that the companies that do best in terms of customer service usually are focused on one or two channels. And so at Help Scout, we’ve always been focused on what are the channels that small businesses in particular really want to bet most on. And that’s been email and then lately Chat. And so we’ve gone really in on those two channels and being able to provide a really human experience along both of those channels.

So today we have not built Twitter, we haven’t built Facebook support, anything like that. Not that companies don’t do that. But there aren’t many small businesses that are doing that at such a meaningful scale that it becomes a really painful problem that they need to solve. So to some extent, we don’t have to think about the latest trends as much as some of the bigger companies do. But I will say that we are working on some AI-based products and we have … I mean, I’ve looked at every bot over the last two, three years. I’ve really been enamored by that space and trying to understand it. And what I’ve learned is that chatbots are a really poor UI in most cases. So what I mean by that is that chatbot doesn’t tell you what it’s capable of or not capable of.

You have to guess, right? So there’s … The UI is completely invisible. All you have is something that will respond to something that you type, but it’s not quite clear enough. So some of the best practices, some of the chatbots out there that are adhering to these best practices will ask … The chatbot will ask a question and you’ll get a choice of like maybe two or three options and you click one. That’s a little bit better, but to some extent, I don’t understand why we make it so open-ended and pretend that these things are smart.”