October 30

Brandon Bruce COO, Co-founder at Cirrus Insight


Brandon Bruce grew up in a tiny California town of 800 people where he only had one classmate at a school with no running water. He went from these humble beginnings to now co-founding and growing Cirrus Insight to $12 million in annual revenue, 65 employees, and #41 on the Inc. 500 list.

Cirrus Insight is the highest rated sales platform of all-time for perfectly connecting Gmail and Outlook with Salesforce. Since launching in 2011, it’s been a roller coaster of success and setbacks, and Brandon’s philosophy for operating Cirrus is similar to his love of competing in 500+ mile ultra-endurance races - you aren’t going to win at the start or in a sprint at the end. Success is a war of consistency and persistence, and he has always enjoyed that.

Brandon has grown Cirrus as a lightly-funded distributed company via scrappy tactics in the same industry as billion-dollar software companies and competitors with tens of millions in funding. Today, Cirrus is in the middle of their biggest challenge yet - pivoting for the first time in seven years after losing their primary marketing channel as the #1 app on the Salesforce AppExchange.

Podcast Highlights:

  • Hire employees who want to be founders. They bring passion to the job
  • Crowdsource new ideas from your clients that way become more relevant 
  • Hire generalists because they can wear many hats

Contact Brandon:

[Podcast Transcript Using Artificial Intelligence]

Umar Hameed 0:06
Are you ready to become awesomer? Hello, everyone, this is Umar Hameed, your host and welcome to the No Limits Selling Podcast, where industry leaders share their tips, strategies and advice on how to make you better, stronger, faster, get ready for another episode.

Umar Hameed 0:35
Today I'm privileged to have Brandon Bruce, the CEO and co founder of Cirrus Insight. Brandon, welcome to the program.

Brandon Bruce 0:42
Thanks so much for having me excited to be here.

Umar Hameed 0:44
So Brandon, in 90 seconds, kind of tell us who you are and what you do.

Brandon Bruce 0:48
Yeah. So Ryan, half my co-founder, and I started Cirrus Insight at the end of 2011. Simply because Ryan saw a gap in the market, he saw a lot of people using Salesforce growing platform for customer relationship management. And then a lot of companies starting around then started moving to the cloud. And that meant they were moving to Gmail. And there was no connector that would connect Gmail with Salesforce, you had all your customer communication happening in the inbox. Meanwhile, you want to capture that data into your CRM platform. So you could track customers over time,

Umar Hameed 1:20

Brandon Bruce 1:21
And so we built this little extension that fits in the Chrome and Firefox browsers for Gmail users, that basically keeps you logged in and keep Salesforce visible in the side panel of Gmail all the time. So you're constantly getting good information from your database. And then you can populate good information based on the conversations you're having back in the Salesforce. And then since then, we released mobile apps for iOS and Android as well as a plugin and add in for Outlook users. So essentially, we're kind of the go to company for inbox and calendar connectors for Salesforce.

Umar Hameed 1:55
And you're doing pretty well. I was looking online like your number 41 and the Inc 500. About $12 million in sales 150,000 customers. So tell me when the idea first came up? What made you decide to go down this path? And what was it like in the first month of trying to get this thing started?

Brandon Bruce 2:12
Yeah, interestingly, for me, it was an easy decision to go down the path because Ryan, and I go back a long way. We've known each other almost 20 years. So we were great friends in college. And so you know, when a college buddy calls you up, you're sort of intrigued as to what they're up to, and how you can be a part of it. And too, I always wanted to be part of a startup, you know, Ryan, and I had done kind of projects together, but none of them had reached the level of a full fledged company. And so when he called and said, Hey, I'm starting to build this app. And I think it's an interesting space. Do you wanna take a look at it? Do you think, do you think it'll have legs. And so I got to essentially work the phones, right, get out call all the partners in the ecosystem called potential customers put up a one page website to see if anyone was interested in being in the beta group of this little extension that would connect Salesforce with Gmail. And so we got about 1000 people in that pilot group providing feedback. And it was based on that feedback that we kind of got the green light to launch, if you will. So the feedback generally fell into two buckets. One, this is really early, you've got a lot of work to do, there's a lot of features that you can and should add. And the second bucket was, and it's providing enough value today that you should launch it, and we would pay for it. And so is based on that second bucket of feedback, we decided, you know what we should really get this out to market. And so I built out, you know, a slightly larger, slightly more professional looking website. And as we got ready to launch that I was kind of in a race to get it launched. Because I knew my son was going to be born any day at that time. Wow. And so I want to get lunch. So I launched that midnight, my son was more in the next day. But even before it officially launched, Google had indexed it, we hadn't checked the box in WordPress that said, Keep this website secret. And one of our pilot users found the new website, found the order page and submitted an order. And we hadn't even tested that yet. But they tested it and it worked. So we got this alert on our mobile phone saying, hey, some money has gone into the bank account. And on the one hand is like Well, great website works. And on the other hand, we were like, well, we weren't going to charge our beta users yet. We want to say thank you for providing all the feedback, we were going to give them an app for another few months for free. So I called that user and said, Hey, you know, we can refund this, we're not going to charge you yet. We just want to say thank you. And they said, Tell you what, I'm gonna buy it in a few months anyway. And so why don't I just be your first customer and that really gave us a big shot in the arm like look, if people are willing to pay for they're getting enough value out of it, where you know, they're willing to part with their money in exchange for the value the apps providing, you know, we should get it out there to market and and so we did and I'm glad we did that was kind of best decision we made. We were considering, you know, wait for six months and put a bunch of new features in or launch today. And I'm glad we launched because it got us out first to market we were able to book those first 500 customers kind of start the cash flow machine and and that helped us establish that beachhead in the market before first few competitors were able to get in, you know, three to six months later.

Umar Hameed 5:03
That's brilliant. So tell me about those conversations with people to get the first beta people to kind of give you some feedback before the product existed. Tell me about that process, because a lot of people would have, you know, gotten 10 or 11, you got 1000. So what was the thinking behind it? And how did you managed to, to land 1000 people, because that's a hard trick to do.

Brandon Bruce 5:22
Yeah, I think it was a combination of a few things. And one credit to my co founder, Ryan, he essentially, you know, the first dreamforce that he went to, which is Salesforce is big annual conference, you know, this year, 175 plus thousand people went to dreamforce. But back then there probably like 15,000. So he went to that conference and basically handed out, you know, business cards that said, you know, I'm making an app that connects Gmail with Salesforce. So if you use both of those, then you can try it for free and provide feedback during this beta period by going this website. And he handed out a lot of those cards. So that got us the first initial cohort. And then I essentially tried to work the phones and call all of the Salesforce partners that I could find. So these are consulting firms that help other companies develop and deploy Salesforce. So I said, Hey, on behalf of your clients, do you want to test this out? And do you have any clients that would be interested in testing this. So those became good feeders of not only those partners themselves, which are kind of aggregators of deep knowledge based on their client experience, but also their clients that are early adopters that want to get in. So we got those folks in to provide feedback. And then the third thing, where we found a lot of users were online forums. So these were places where people were essentially raising their hand and expressing pain, right? using Gmail, I'm using Salesforce, there's no way to get these emails into Salesforce, I can track them. There's no way to, you know, sync my calendar events in or create new leads and contacts as soon as they email me. And we're like, Well, hey, this is this is why we built the app, will you provide feedback, so we can make sure it does exactly what you want. So it conforms to your use case. So the people on the forums are like, Oh, great, so someone out in the wide internet is listening, and I can be part of the process and crafting the app. So I feel like for those folks, both for the partners and for the people that were posting the forums, we gave them a voice early on in the product process. So they really, my hope is they felt like they were really on the team, the product team, they were helping us to define and spec, what would go into the product, what wouldn't? How would it work? What would it look like, by providing their feedback, and people enjoyed that, right, it's fun to be sort of on the ground floor of deciding how something will function. And so we owe a tremendous amount to all those folks that were willing to get in early with us. And on the plus side, we also delivered them something that they could use early on to save a lot of time, that's mostly our user reviews tend to fall into two buckets among Sales Users. This saves me a lot of time. And among managers that this is helping me to get people actually to use Salesforce, because they don't have to go log into Salesforce anymore. They're just constantly logged in to the inbox.

Umar Hameed 8:05
Brandon, how many people in your company right now.

Brandon Bruce 8:07
So today, we have 54 people, which is pretty evenly split between where I sit in Knoxville, Tennessee, we have our sales, marketing and support teams. And then Ryan sits in Irvine, California, and runs our product team, which is you know, product design, management in engineering.

Umar Hameed 8:24
So tell me, how many salespeople in the company?

Brandon Bruce 8:26
Officially about 10. Salespeople, you would call it more than that closer to 15. If you consider that our customer success, and our sales team, you know, pure sales team all do sales, the success team is involved in expansion. So add on sales as well as you know, upsells from from one tier to another pricing tier.

Umar Hameed 8:50
So tell me when you get started. Was this just self funded by you guys? Did you get investors in? And when did you hire the first employees?

Brandon Bruce 8:58
Yeah. So when we started, you know, bootstrapped Ryan and I ran it together, just the two of us for the first nine months. So Ryan was heads down coding and architecting the app and incorporating all the feedback we were getting from the from the pilot users. Meanwhile, I was going back and forth between trying to get new sales, doing demos, supporting the customers that have come onto the platform. And then, you know, keeping the website up and trying to do kind of the basics of guerilla marketing on essentially zero budget. Nine months in, we had pitched to an interested strategic investor that had come to us and said, Hey, we like the space and we like the app. You know, we'd be interested make an investment. And so that was the opportunity that we really took to write up the first formal business plan to actually put pen to paper and say, This is our plan for the next year. If we had money, this is how we would spend it and what order and what things would be prioritized. And we were going down that path with them. Well, then that company got acquired, which shut down All of their m&a and investment activity. So we said, Oh, shoot, we were getting excited about the possibilities. Thankfully, those angel investors came behind and said, We like that plan that you developed for this strategic will fund it. So nine months in, we got some angel investors on board, which really helped on two fronts, just a, we had money in the bank, which helped us even out kind of the ups and downs of cash flow, right. So one day, we think we're really onto something, and the next day or week or month, we would be like, shoot is that it are those all the customers do what happened? So, you know, cash flow was Rocky. And so that helped us to kind of smooth out that cash flow, which then in turn gave us the psychological permission, if you will, to go out and hire the initial employees and feel like we could make a commitment to them, right? If they're going to come in, and really work hard with us, you know, long hours, try to work smart definitely work hard, then we'd be able to pay them every month. So having that money in the bank helped a lot with that.

Umar Hameed 10:56
As you guys are thinking about the company, some people think about the culture and what they want the mindset of the people to be, you know, somewhere in the future when they get to it. Did you guys give any thought to that thoughts to that before you started hiring people? How did you manage that? And how are you managing it now that you're a much larger company?

Brandon Bruce 11:13
Yeah, I mean, I, it's fair to say that we gave some thought to it. At the same time, the culture is largely infused, I think, by the founders personality. The things I remember that we talked about when we first started is, hey, when we go to hire employees, we're looking for people that are that are generalists. They're smart, they can do lots of things, because we have lots of things that need to get done. So it's not just fitting into one small section of the company, it's the ability to dance between, hey, we're gonna do sales. But if we also need you to help on the marketing side, or support, or, you know, QA of the product, that you can do that, too. So we wanted people that were flexible, you know, that were smart, that could apply their smarts to lots of different aspects of the company, to I remember that Ryan and I talked about, hey, it'd be great to find people that themselves are interested in starting companies, right? If they're an interested, past founder, current founder or future founder, then that's the type of person that we think would fit really well with us, because we're founders and so we can all learn from each other. And if they want to start their next company in, you know, three to five years, let's say, they can see the mistakes that we make and avoid them in the future. But then they can also see the things that work for us, and then that'll be a really beneficial experience for them. Meanwhile, they've contributed the great energy that a founder type brings to the organization. So that was kind of the profile that we looked for in our in our first hires.

Umar Hameed 12:45
So how did you articulate that? Will you ask them, were you a founder? because that's really intriguing, because a lot of times, people are looking for the task at hand. And what you were looking for what you've described is, hey, we're going to be in founder mode, which means a lot of shit needs to get done. So we need people that are generalist that can do stuff, and have the mindset to shift. And then also, how do you getting people that are thinking about founding companies brings a level of passion and energy that you wouldn't find in employee? So how did you ask people around that?

Brandon Bruce 13:16
It's kind of a, it's kind of an ownership mentality, right? And so all of our employees benefit from, from from stock options. And that was true to the first employees to that place today. But yeah, it was a matter of, you know, looking through applicants if they were applying for the job, but of course, a lot of those early hires and still hires today, most many, most of which come to us by referral. So you know, reaching out and having good relationships with the top local universities, University of Tennessee Maryville college, have referred us a lot of their top students, but also top alumni. So we would ask, Hey, are there folks that graduated in the last five years or so that have gone out that have started their own companies that are in on the ground floor, other companies that are interested in a change, right? Or have they exited their previous company? Or did their previous company not work out, and they'd like to join ours? Because they're that type of person, right? They're not looking for, that didn't work out, I need to go seek security and stability. It's like, oh, that didn't work out. But it was so exciting and awesome. And I want to try it again. And surely the next one will be hit. And so through those referrals, we got a lot of the right people that had on their resume, either, you know, they've done something in the past. They're doing something now, but they'd like to pivot and do something else, which is join us or that they have that interest in the future, right? Someone's just gotten their MBA, they're talking about founding something in the future, they're not really sure what that's going to be yet which describes I think most of us, right, it's like we know we want to start something we're not sure exactly what it is maybe even what industry it's in, but the energy is there and the idea that you're a generalist and you can add value in lots of aspects of a company is there, just Hey, join, you know, join us for a while for as long as we can keep them to be honest. Because we have had people leave, and many of those people have started their own companies. And that's that, you know, so it's a double edged sword. It's like we wanted those people, we got a number of me. And a number of them subsequently after three to five years did leave. And that's hard, because we want to keep them and we keep them as long as possible. But we also recognize like, yep, that that's what we saw on them at the beginning. And they knew that about themselves. And so, you know, blessings to them, right. We know the road that they're on. And we try to encourage and help them any way we can. And they're often the folks that are able to, you know, feed back loop to us and help us the most, because they're 100% in the game, their fellow founders. So But yeah, I think that's interesting thing, if you're founding, why not get a whole team, of other people that are founders or like them.

Umar Hameed 15:44
Tell me, oftentimes, in larger companies, let's say, there are people in different departments and different departments have different agendas for your company is kind of small, but you have the product side of things. And you have the sales and marketing side of things that touch customers, how do you keep the two groups aligned? So you guys are supporting each other building products that are relevant to your community?

Brandon Bruce 16:08
Yeah, I mean, I think that's one of if not the fundamental challenge of any software company, really any company in general, but I'll speak from the software perspective, is because that's what led to our initial reception, and success in the marketplace was that we had listened so much to all the feedback from those beta users, that we were able to incorporate their top suggestions into the app. So we didn't need to say, you know, this is something that Brandon decided was a good idea was like, nope, none of my ideas made it into the initial release of the app, because we had plenty of ideas from people that really needed to use it. You know, we've been able to add in our own personalities and our own ideas for some of the best features. But, you know, for honest, and we look back, it's the features that came to us in the idea forums, that that really defined the best possible use cases of the technology and will continue to do so I would submit in the future. So to keep the teams aligned for one, it is in our internal, you know, kind of culture document on several different slides. But I think the most, the one that resonates the most says, you know, we have each other's back, which means for the customer facing folks that you know, the product team, really through a concept of, we consider kind of an internal SLA, a service level agreement, right product delivers to the rest of the company, a product that is solid, right, when we say that we have a feature and that it works, that's a brand promise into the marketplace. And we need to be able to defend that promise. And be able to go to customers and say, This is how it works. And it works like this every time etc, etc. Meanwhile, we need to be able to defend the product when we're talking with customers. So if the customer finds a bug, which, you know, spoiler alert, there's bugs in every piece of software, no matter how big the company is, you'll find them from time to time, in Google products, Apple products, etc. And these are the you know, best and brightest, biggest companies in the world. It happens. So you know, customer finds a bug and we know how to handle that we know how to get the feedback back to the development team and get that fixed or addressed or otherwise answer the customers questions. So, you know, technologies we use, we're a big user of slack. At the beginning, I was like, do we really need another messaging platform, but it has taken over for internal email for us. And it's been a great tool. We use JIRA for managing the whole development pipeline. And that's been helpful just for visibility, the support team puts in the jiras puts in, you know, here's the background, here's a video of what's happening, what we need to get addressed. And then Meanwhile, engineering is able to come up with original ideas or original ways to solve problems. And that's an important thing, I suppose to point out, the end user will sometimes say I want to be able to do something. And I remember originally asking them, well, how would you like us to do that? How do you want to be able to do that? And the person said, I don't know you're the ones that are making the software just enable me to do it, right. And so frequently, there's, I want to be able to do something, but I don't know how I want to be able to do it, can you guys figure out a good way to present that from a user experience standpoint, and get it into the app. So our engineering team is able to then send through a staging environment as well as mock ups, etc. Here are some options, here's how we can get there. And then we can take that through our success team to existing customers, and to the sales team to prospects and say, What about this, you got three options? Are any good? Does one stand out? In which case we'll run with that one? So that's kind of the process in a nutshell that we use

Umar Hameed 19:37
Brandon, before we part company, I was looking at your bio, and there was something about ultra endurance events. Tell me about that.

Brandon Bruce 19:47
Yeah, so most recently, I did a great bike ride, which those of us in the cycling community would call an epic ride from Knoxville, Tennessee, where I live down to Daytona Beach, Florida. So it was 1098 miles In 11 days, It commemorates the number of wins that Pat Summitt had when she was the coach of the lady volunteers basketball team at the University of Tennessee. So they won, you know, multiple national championships, one of the most famous coaches of all time, you know, wrote books, she's got the path definitely doesn't that are used by lots of organizations around the world to kind of define excellence and culture. And so she passed away of Alzheimer's a couple years ago. And so we did the ride to raise money for a big Research Initiative, the Alzheimer's research initiative at University of Tennessee Medical Center. And yeah, we hit the road. So I've been a longtime cyclist, I've done a lot of endurance events over the years when I lived in California, did a lot of 200 mile races, lots of centuries, and then a race to Death Valley, which at the time was called the furnace Creek 508. So 508 miles through the desert, which was pretty awesome. So this ride was great, we got one day rained out by Hurricane Michael. And so we actually took the ride indoors, and did about 55 miles on a spin bike. So for those listeners that maybe do a spin class, from time to time, we were in there for, you know, two, two and a half hours to knock out 55 miles and the the scenery does not change. So I highly recommend biking outside. But if you do need to get inside, you can you can get a pretty solid workout that way, because there's no, there's no coasting, and there's no drafting, you just have to knock out the miles. So we did that. And then we loaded up the other days with additional mileage we did about 135 for three days in a row made our way down to Florida and reached our goal. So anyway, a ton of fun and raise money for a good cause I was happy to be part of it.

Umar Hameed 21:32
Brilliant. The one thing I'm taking away from this conversation, Brendon is that the genius of what you guys have done is reach out to the audience and ask them what they really want. Is this a good idea? And if they want features changed, going back to them and saying, Is this what you're thinking? Here's three ways to do it, which one works best for you? And just having that finger on the pulse of your constituents allows you to be relevant and deliver high quality products, do I have that right?

Brandon Bruce 22:00
Yeah. And I and I think it's fair to say it's kind of a it's kind of a return to basics, right? We all, we all hear that advice pretty consistently. And we're like, you will Yeah, of course. But it turns out, it's hard, right? Yeah, those are, those are long calls. I mean, I remember spending two, three hours on the phone with one person really trying to get to the bottom of what they wanted to see. Because sometimes it's hard if people haven't thought of it before. The initial reaction is quick answers, right? Hey, would you like the app to be able to do this? Yeah, sure, why not? Right, the more the better. But it turns out, you know, after a couple hours, they might backtrack that and be like, actually, that could be kind of complicated for our users, we might want to keep it simple, right and less training for us. And it'll be easier for our users to adopt it. So then you've kind of come full circle. So it's been willing to have those longer, you know, getting into the weeds conversations with possible customers and partners that I think gave us the best information. And that continues to be true today. And then of course, the really high level provides that was you know, sounds good when they come back to you and say, Oh, this is great, we'd like to buy that. But you're also gonna get a lot of the opposite reaction, I don't like that. I don't like the color you chose for that. I don't like the way that loads took too long, too short, need more training built in need the training that you built in taken out, we want to do our own training, right. So the longer that you're doing it, there's lots of requests for customisations configurability we want to change the language we want the currency to be different, etc, etc. And it's picking and choosing where it's finding ways to you know, sustainably scalably build in these things for various constituencies meaning big customers, small customers, you know, domestic customers, global customers, etc, etc. And so it's part of the fun and part of the challenge is that as the as the technology iterates it almost definitionally becomes more complex. And therefore you have to be careful about what you put in it what you take out at because anything you put in you're probably going to need to support that forever going forward and so it's making that kind of heads up decision. Hey, we're gonna release this and so be ready to support it. Possibly till the end of time.

Umar Hameed 24:11
Brandon, thanks so much for sitting down with me it was a great conversation.

Brandon Bruce 24:14
Yeah, pleasure to be with you if anyone listening is curious if you find yourself in Knoxville, Tennessee, they can join us for a Friday company lunch and if they want to check out the app it's just at cirrusinsight.com. My email is brandon@cirrusinsight.com, if anyone has any questions or just wants to connect, find me by email or on LinkedIn. And yeah, look forward to following up.

Umar Hameed 24:35

Umar Hameed 24:41
If you enjoyed this episode, please go to iTunes and leave a five-star rating. And if you're looking for more tools, go to my website at nolimitsselling.com. I've got a free mind training course there, that's going to teach you some insights from the world of Neuro-Linguistic Programming and that is the fastest way to get better results.


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