Tyler King – CEO of Less Annoying CRM

It took me too long to realize that if you have something customers love, even if it’s not technologically groundbreaking, you should stick with it and improve iteratively rather than trying to come up with totally new gimmicks.

Tyler’s background is in product design and software development. Tyler co-founded Less Annoying CRM in 2009 and is the current CEO. When he’s not obsessing over improving the product, he’s working with the rest of the team to make sure that Less Annoying CRM truly lives up to its name.

Where did the idea for Less Annoying CRM come from?

My introduction to small business CRMs began when my mom joined a direct sales business. The company she joined didn’t offer her any productivity tools so she was on her own to come up with her own system for staying organized. I really saw the opportunity to create a small business-centric CRM at my next job, when my company signed up for Salesforce. It took me — someone with significant programming experience and know-how — a full month to get Salesforce setup for the company. I built a mini-CRM for the company’s insurance agents, and it blew their minds. I saw that opportunity for an alternative to Salesforce that would be more manageable for smaller teams.

What does your typical day look like and how do you make it productive?

As CEO, I have to wear many hats, so being able to prioritize what to work on is key. It’s hard to balance what’s urgent with what’s important. One of the most important roles I have is being a member of the software engineering team, but it can be very easy for me to put that role aside when I need to deal with urgent business issues. To keep everyone (myself included) disciplined about this, we established group programming sessions where twice a week, for 6 hours out of the day, I work with the other developers on nothing but code. During group programming, nothing business-related can distract me. The other three days of the week, I’ll focus on other aspects of the business and that’s also when I can spend some time addressing what’s urgent in the moment.

Another habit that I think is really important is that I make sure to do at least one product demo for a customer each week. That might not seem like a high-impact way for me to spend my time, but it keeps me connected to the customers which improves the decisions I make in other areas of the business.

How do you bring ideas to life?

My co-founder, Bracken, and I work as a team when we create, and we’re each good at different parts of the process. I’m most comfortable working with a blank canvas, so when we’re just getting started, I throw a bunch of different mockups, prototypes, etc. together just to test out ideas. Bracken is more like an editor. He looks at what I’ve started and points out problems and identifies opportunities I’ve missed. By going back and forth a few times, we can normally end up with something really special and then it’s just a matter of building it into our software.

What’s one trend that really excites you?

Since the beginning of the web, there’s been an ongoing battle between native apps (apps you install on your device) vs. web-based apps (apps that run in your browser). I’ve always preferred web apps because they’re built on open technologies and they’re much more accessible to more people, but native apps tend to be faster and more responsive which has made them appealing to a lot of users.

Thankfully there have been some great new technological improvements recently that allow web apps to work more like native apps traditionally did. At Less Annoying CRM, we’re currently moving to a system called “React” which allows our software to be lightning fast and responsive even though it’s running on the web. I’m really excited about what this might mean for the future of technology since I’m of the opinion that proprietary ecosystems like the iOS and Android app stores are ultimately bad for users, so the more improvements we can see in web technologies the better.

What is one habit of yours that makes you more productive as an entrepreneur?

My weird habit is that I’ll go on week-long retreats to Salt Lake City, just working on my individual projects. As the company gets bigger, more of my time is being spent as a manager rather than as an individual contributor. But at an eleven-person company, everyone has to be an individual contributor, including me. Taking these retreats helps me refocus on what I can contribute as a member of the dev team. Why Salt Lake City? No idea.

What was the worst job you ever had and what did you learn from it?

My worst job ever was working at an ice cream shop for a summer during high school. I actually ended up getting fired because of a miscommunication with my manager about the schedule. My main takeaway is that something that was really minor turned into a big issue due to poor communication. If my boss had taken a minute to explain what he wanted from me or if I had been more assertive about asking, the issue would have been easily resolved. Now that I’m in a managerial position, I try to keep frequent open dialog with everyone at the company.

If you were to start again, what would you do differently?

I would put more faith in the value of having a simple, effective product. We got some initial traction with a very basic product that small businesses found easy to use, but when it came time to take the next step, I didn’t think our product was good enough to scale without some kind of novel innovation. It took me too long to realize that if you have something customers love, even if it’s not technologically groundbreaking, you should stick with it and improve iteratively rather than trying to come up with totally new gimmicks.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

No matter how busy you are, no matter how much you trust the people in charge of recruitment, personally interview every single person that you’re going to hire. Staff cohesion and culture are too important to delegate out.

What is one strategy that has helped you grow your business? Please explain how.

Word of mouth has been our most valuable source of growth from day one, and the primary driver of word of mouth for us is outstanding customer service. People talk to our support staff, they have a great experience, and they pass on the good word to their networks.

I firmly believe in the power of incentives. I don’t think any customer service person sets out with a goal to mistreat customers — when bad customer service happens, it’s because there was an incentive to reach a certain quota or to plow through as many support tickets in as little time as possible. But the reverse is true as well. If you want to offer great customer service it’s as simple as hiring people who care, and putting them in a position where they know they’ll be rewarded for making customers happy.

What is one failure you had as an entrepreneur, and how did you overcome it?

The biggest mistake I made in Less Annoying CRM’s formative years was not properly scaling the company’s transition from a remote lifestyle business to an actual company with employees. When it was just my co-founder and me, the two of us handled every aspect of the business and things worked pretty well. As we started hiring people, we figured that a full-time expert in a specific area would be much more skilled and effective than I was spending a small portion of my time on that area. So we ended up throwing out most of the things we were doing that worked and asked the new team to try to re-invent the wheel. The result: we lost a lot of the momentum we’d worked so hard to build, and the expectations of the new team were unrealistically high so our growth stalled.

Eventually we learned to appreciate and respect the early success we had, and to use that as a starting point. Now when a new hire starts, we spend a lot of time showing them how we currently do things, then we ask them to take over, and only after they’re comfortable with the old way is it time for them to start trying to introduce new ideas. By going back to our roots, we’ve been able to restart growth and get the company back on the right track.

What is one business idea that you’re willing to give away to our readers?

I think that there’s a huge opportunity building technology to help communicate with our elderly family members. The Baby Boomer generation is aging, lifespans are longer than ever before, and the growing elderly population is vastly underserved by tech companies. We have great tools for communication, but they aren’t truly accessible to the elderly.

My Grandma lives in my parents’ basement. She values her independence, but my parents still need a way to make sure she’s okay every day. I know there are millions of other families like ours just in the U.S. and I think there’s a lot of money to be made and good to be done by helping out with those types of problems.

What is the best $100 you recently spent? What and why?

I just bought a few board games for the office, and I think that it’s hard to beat the value of a good board game. We have an amazing team working together at Less Annoying CRM and it’s really great to spend some time hanging out and getting to know each other outside of the work context. These board games have given us endless hours of entertainment and we’re a stronger team because of it.

As a matter of fact, board games have been such a positive influence on our teamwork that we’ve started incorporating them into our hiring process. There’s a game called Pandemic where everyone is on the same team, so it’s cooperative instead of competitive. We’ve started playing Pandemic with new hires during the interview process and it’s a really great way to see what it’s like to work with them and see how they interact with others.

What software and web services do you use? What do you love about them?

I love software, but it’s in my nature to be very critical of anything I use. So there aren’t many pieces of software that I unconditionally love, but there is one that comes to mind: Dropbox. In my opinion, Dropbox is the most obvious no-brainer investment that every single person should make whether it be for professional or personal use. For starters, it provides absolutely essential functionality by backing up your files automatically and making it easy to access any file on any device. Whenever people lose a file I have no sympathy because it’s just so easy to have everything automatically backed up these days.

But aside from the functionality, what I love about Dropbox is the lack of an interface. Once you install it on your computer, you can just forget about it. You just keep using your computer the way you always did, but now you have peace of mind and a few nifty extra features if you ever need them. They are one of the purest forms of “less annoying” software that I can think of.

What is the one book that you recommend our community should read and why?

Right now, I’m reading Startup CEO by Matt Blumberg. He does a good job of talking about the actual mundane day-to-day decisions a CEO has to make. Most business books are high-level and inspirational — which isn’t a bad thing — but those high-level concepts don’t really give you any solid tips you can act on.

What people have influenced your thinking and might be of interest to others?

I should start by saying that I mostly look to my family, friends, and employees for advice and leadership. But since your audience doesn’t have access to my dad, I’ll list a few online thought leaders that I admire: I follow Jason Lemkin (SaaStr), Paul Graham, Patrick Mackenzie (Kalzumeus), and Penn Jillette (the magician). I specifically want to call out Penn because I think he gets dismissed since he’s a magician, and most people (including me) don’t really care about magic. But I think he is one of the most talented communicators out there. I don’t agree with everything he says, but there’s no one better at laying out an argument in a way that is logical, emotionally compelling, and incredibly entertaining.


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