"Warren Buffett said “emotional stability” is the key to success and that has stuck with me. A startup is a roller coaster."

Brandon Bruce is co-founder of Cirrus Insight, a sales productivity software company in Knoxville, Tennessee that was recently named #41 on the Inc 500 list. Brandon is 6’8” so he’ll be easy to spot at Dreamforce in San Francisco next week.

Q: Please tell us a little bit about your company – what is Cirrus Insight all about?

Cirrus Insight is all about helping sales teams to be more efficient and effective. Cirrus Insight is the top rated sales application on the Salesforce AppExchange with 1,500 reviews, 5,000 customers, and 150,000 sales professionals. It helps drive productivity and performance by bringing Salesforce into the inbox and calendar where people work.

Q: Please tell us a little bit about your background and how you started your company?

I’m a small-town kid from Los Olivos, California population 800. I was in a class of 2 people in grade school. I did structured activities in school, but I also had a lot of unstructured time to pursue my own interests at my own speed. I think I’ve been drawn to entrepreneurship ever since. My co-founder Ryan Huff and I have been friends since freshman year of college at UC Santa Barbara. He’s a great product architect and designer and I love the challenge of the taking the product to market. We’re a great team.

We started Cirrus Insight in 2011. It was the first application to connect Gmail with Salesforce. Today, we connect Salesforce with Gmail, Outlook, iPhone, iPad, and Android so we’re able to serve sales professionals in the office and on the move. It was just the two of us when we started. We’ve been able to scale up the company over the past 5 years to more than 60 employees in Knoxville, Tennessee and Irvine, California.

Q: What are some of the projects you are working on right now?

We’re getting ready to launch a new sales platform we call Flight Plans which will enable sales teams to accelerate their sales pipeline with a library of marketing-approved email templates. They’ll be able to set up one-to-many drip campaigns of emails and phone calls to reach prospects and customers. And they’ll be able to see which campaigns perform best with key engagement metrics like opens and click-through rates. Plus, we’ve built a proprietary outcomes algorithm to tie sales activities to revenue. We’re really excited about Flight Plans.

Q: Quickly describe what an average working day is like for you?

I like to get up early around 4am. It’s probably a vestige from my days rowing crew at UC Santa Barbara. It’s quiet and I can get ahead of the day. I like to run or take a bike ride or go paddling – something outdoors where I can get a sweat. I can also usually do one or two of the most important things on my task list for the day before everybody wakes up. I then have breakfast with my family, take the kids to school, and head to the office to work with my team for the day. I return home for dinner and family activities, and I usually end the day by wrapping up any unfinished business, reading, and planning to do it again the next day.


Q: What would you say are the top 3 skills needed to be a successful entrepreneur, and why?

  • Warren Buffett said “emotional stability” is the key to success and that has stuck with me. A startup is a roller coaster. There have been days that were unbelievably awesome, and other days that have been painfully difficult. It’s a skill to stay on an even keel.
  • Pat Summitt was the coach of the University of Tennessee women’s basketball team here in Knoxville. She’s the winningest coach in NCAA basketball history, and she was first and foremost a competitor. She said, “When you choose to be a competitor you choose to be a survivor. When you choose to compete, you make the conscious decision to find out what your real limits are, not just what you think they are.” I think being competitive is key for entrepreneurs.
  • Jason Lemkin recently posted that the best founders are somehow indefatigable. I love that. As a marathon runner and endurance cyclist, the idea of persevering and outlasting has special appeal.

Q: What are your plans for the future, how do you plan to grow this company?

We’ve built a great customer base. We plan to continue to the grow the company the same we have for the past 5 years, which is listening to our customers and building the tools they want and need. It seems simple enough, but it’s easy to get distracted in the fast-moving world of software.

Q: How are you funded? What is your best advice to entrepreneurs when it comes to raising funds?

We’re primarily customer-funded. We’re very grateful to have received support from several early angel investors. But we haven’t raised VC. My best advice is to start selling. The best funding is the funding you earn from your customers.

Q: How many users or clients do you currently have, and when do you consider your company a success?

We have 5,000 customers and 150,000 users. The yardstick for success keeps moving, which is as it should be. I think we’ll always feel that we’re a scrappy startup that needs to hustle to retain the privilege of serving our customers.

Q: What were the top 3 mistakes you made starting your business and what did you learn from it?

  • I didn’t implement a system for invoicing for over a year. Most of our customers pay by credit card, and when we started winning bigger contracts, I just sent out invoices ad hoc. A year later we had to spend several all-nighters to get organized and implement a billing system.
  • I didn’t sufficiently market-test a few of our ideas. We spent a lot of time and resources pursuing several product ideas that had promise but that we hadn’t sufficiently market-tested to see if they warranted the investment. More important than the cost of these projects was the opportunity cost. Our big advantage as a small company is being fast and nimble. We have to keep our focus to maintain our advantage.
  • I signed a couple contracts with flexible out clauses. It was against my better judgment at the time, but we really wanted to get the customers and make them happy so we agreed to the terms. In both cases the customers exercised their right to cancel and for good reason – they were migrating to different technology platforms. But it was a reminder that both companies weren’t right for us in the first place. We haven’t signed a contract like that since.

Q: How do you go about marketing your business and what has been the most successful form of marketing for you?

We like to do in-person events. We also use marketing automation tools and we spend a lot of time on web content, but there is no substitute for meeting with customers face-to-face.

Q: What was the best business advice you have ever received and who gave you this advice?

Early in the life of the company I gave a demonstration of our software to a prospective customer. I told my wife about the call. I was enthusiastic about it because I was able to highlight all the key features and my pitch had a good cadence. She was unconvinced. She asked a number of questions. What did the customer say during the call? Did the demonstration focus on what the customer wanted? The implicit advice was to refocus all future communications on the needs of the customer. That’s been vital for me and for our company.

Q: Say I was starting my own version of Ciruss Insight what advice do you have for me?

I would advise you to start a different type of company. And that’s not because I don’t love our company or the competition. It’s because there are so many current players moving so fast in the sales enablement and sales acceleration space that there are probably better opportunities for brand new companies in other areas.

Q: What are the top 3 online tools and resources you’re currently using to grow your company?

We do a lot of events so we’ve been using Eventbrite quite a bit. I’ve been using LinkedIn every day. And internally we use Slack and Trello for team collaboration and project management.

Q: What’s your definition of success?

I’m really not sure. The word success sounds like an end state. It’s hard to picture an end state to what we’re doing.

Q: What are three books or courses you recommend for entrepreneurs?

3 of my recent favorites are:

Q: If you had the chance to start your career over again what would you do differently?

I would start a company earlier. I’ve learned a tremendous amount in the short time we’ve been running Cirrus Insight, and it’s been a lot of fun. I would launch a company in high school. I did a lot of entrepreneurial activities and read a lot of books in school, but there isn’t really a substitute for the accelerated learning that has been made possible by getting out into the marketplace.

Q: What is your favorite entrepreneurship quote?

I really like this Albert Einstein quote:

“I have no special talent. I am only passionately curious.”

Q: How can our community get in touch with you?

I’m at Brandon @ cirrusinsight.com and I’m on LinkedIn

Crunchbase: https://www.crunchbase.com/organization/cirrus-insight#/entity

Twitter: @cirrusinsight