Learning To Win At Problem Whack-A-Mole With Rajeev Gupta

We have another great business owner interview for you. This business owner, like many of the others we’ve done, his company was recognized in the Inc. 5000 list of fastest-growing companies in the US for 2019. He was also recognized in the Startup 50 and the FT500, the Financial Times 500, with lots of great recognition. The leader of this company is Rajeev Gupta. I’m super excited to welcome you to the show, Rajeev. Thank you for joining us.

Thank you, Brett. I’m glad to be here.

I’m going to share a little bit about your company for some context and then I’m going to have you fill in the blanks where I got it wrong. Rajeev’s company is called DBSync. DBSync was founded in June 2009. Initially, that company served as a product line of another company. Their business has headquarters in Nashville, Tennessee and operations in Bengaluru, India.

Rajeev makes his home in the Bay Area in California. DBSync is uniquely positioned to lead the integration and replication platform space with innovative SaaS and on-demand services and solutions. He’s a seasoned technology expert and a SaaS CEO leader. I’m grateful that Rajeev would make the time to be with us.

Thank you, Brett.

I failed to mention that you earned an MBA from the Owen School of Management at Vanderbilt University. I’m guessing that the school of growing a startup is probably a little more valuable to you than that MBA. Am I right?

I learned a lot more working with another startup. I realized how different the world was. My background was working with large corporations like GE or McGraw Hill. When I joined the startup, it rewrote the way I thought about everything, the business and software world. My MBA was a great enforcement of thinking differently. These are the moving parts of a business and how to handle those but the kick came from working for a startup.

Sometimes we might get 1 guest or 2 sneaks in here that have bigger company experience. They do what I call corporate speak. It’s hard for entrepreneurs, not because they’re not intelligent but because it’s a different world. For you to have the experience of both being in a startup where maybe you weren’t the owner and being in a startup where you’re the CEO, you’re leading it. Those are invaluable experiences that our audience will love to learn from. Thank you so much for taking the time to be with us. I’m not super familiar with the type of work that DBSync does. Would you like to share briefly what that is and give our audience a little better feel for that?

This whole thing started as being a part of Avankia. Avankia was a consulting firm, one of a couple of companies that I’m involved with and own. They were primarily doing consulting services. Around 2006 timeframe, we stumbled into Salesforce.com implementation for one of our customers. We liked it. We said, “The SaaS thing is coming through. Why don’t we see what this is?”

We pitched a couple of ideas to Salesforce. Around the 2007 and 2008 timeframe, we got incubated. They incubated 10 companies, which grew to 30 and more. We were one of the first ten companies that they incubated. We came in and were like, “The SaaS and cloud are exploding. Let’s try.” We were throwing darts on a board and seeing what stuck.

We tried many things, as most entrepreneurs do. There are more failures than success. Fortunately for us, two of our products started moving in the market and selling. One was DBSync, which I have. Another one was TargetRecruit. We took these in 2009 and spun them off. We recruited TargetRecruit. We exited that company in 2018. My focus is on DBSync, growing it and seeing where we can take it. It was an interesting experience to see how this whole evolved and how Salesforce played a key part in building these startups, which I’d like to thank.

That’s a great background. Thank you for that. We didn’t talk about this before the official interview started but that’s how my company started as well. It wasn’t with Salesforce but it was with another software company. It’s like Salesforce.com but for small businesses. It’s called Infusionsoft. We started up this business inside of that software company. A couple of years ago, they decided not to do some of these other things anymore. I bought it and we spun it out. You and I share a little bit of a path like that.

As the SaaS and Infusionsoft were growing, my background working for GE and others was mostly around building integration engines and rules engines. When I saw the SaaS environment and ecosystem grow, I said, “If everyone is buying software on the cloud, they’ll also integrate on the cloud.” We approached DBSync as cloud-to-cloud or cloud-to-on-premise data integration and replication.

Over the period of the last decade, we have continued to work on it, trying to find the right solutions for these companies adopting Salesforce.com or Microsoft. Also, integrating with QuickBooks. We are one of the leading ones within that space of cloud data replication around archiving backup recovery. Cloud solutions have to be backed up. Most of these providers don’t provide the full breadth of the backup archive. Those are the things we started filling in, much like you, Brett, finding the gaps, which the paid company doesn’t want to get in on. It’s not involved in trying to fill those things. We found that opportunity, expanded into it and that’s where we are.

Thank you for a little bit of that background. Let’s get into the part that my readers are excited to know. What are some of the learnings that you’ve had along the way? We talked about this briefly before the recording started but we love to hear from business owners who’ve seen their businesses cross that million-dollar mark. They keep growing but it’s not all smooth sailing. There are new challenges that happen. You’ve figured out some basic things to get to a million in revenue.

You’ve got a good product. You’ve figured out some product market fit. You’ve figured out some marketing and sales but there are new challenges around building the team, aligning the team, scaling the company and all of those types of things. That’s where we’d like to sink our teeth in with this interview. If you wouldn’t mind, reflect a bit on those times when you started to experience new challenges after figuring out some of the sales and marketing things.

We grew organically. Leads came to us and we were closing a lot of it through the Salesforce ecosystem and a couple of other ones that we were playing through. As we hit that critical seven-figure mark and go beyond, the first thing came, I always say a startup is like the game of whack-a-mole. You hit 1 and 2 pop up or 2 other problems pop up. We were fighting those constantly. I started reading quite a bit about how you manage many. I can’t run this the way GE would run our big corporation. I have to be nimble as well as be able to produce and move forward.

I ran into a book. it was called Rocket Fuel. I’m not sure if you know it. They call it the Entrepreneurial Operating System. I read it and we said we were going to implement it. We took a leap of faith. A couple of us went through it. We spoke to a couple of experts and we started implementing it. In the first few quarters, we could see a substantial change in the way we work.

It caught the team aligned together quite a bit. It gave us the focus and quarterly goals. We reorganized a little. Part of it was I started to delegate things. If you are in $1 million or even more, the CEO is very much involved in pretty much everything. At that point, you have to let go of a few things. Trust others to do it. In this framework, there’s the role of an integrator. Think of it as a COO of your company. He would manage. I would focus more on the creative and innovative side. That helped.

We still do practice the EOS framework. This framework, if you read through it, is pretty good if you are less than 250 employees. That’s what the benchmark is. If you grow beyond that, it becomes a problem to manage. You might want to look at some other methodologies. The EOS was one thing from a management style that we changed. The other thing that I look back on is we grew up as a products company and most of the Silicon Valley startups come up with that. We have a product and a couple of early adopters. The CEO is able to communicate and go through it.

Winning At Problems: If you grow beyond 250 employees, it becomes a problem to manage. You might want to look at some other methodologies.

Post that, when you start to hit the gas pedal and you are growing, then messaging and positioning become very important. That’s when you have to narrow down your messaging or in our case, we built out our messaging. We started and engaged folks like Gartner and others to craft out what we should do and focus on. We implemented a couple of messaging frameworks and positioning. If you look at Crossing the Chasm book, you’re still in the chasm zone. You’re not out of it. You have to propel yourself out to it.

Fortunately for us, we were profitable at that time. We were not hitting it. Usually, most of the other companies that I’m involved with are still in the chasm space. Focusing on getting out of the chasm to profitability becomes important. You do it by scaling up quickly and getting out of it. Until then, the first million is usually inbound. The early adopters coming in post that you have to hunt for your deals. That’s when you start looking at partner channels and all the distribution channels through marketplaces. You start to expand all and start building those relationships and step forward. That was one.

The focus was the other thing. While we came in and said DBSync would be a cloud data integration and replication, there are hundreds of SaaS applications across. We always had to pick and choose which segment we should go after. If we go after in a way crowded field, it’s tough to win. We ended up with a lot of critical partnerships where we had a focus. We went in and won the deal. Our strategy was to go deep and win rather than go broad and try to address all the markets that we could potentially play in. That’s a high level.

I spent some time at a tech company and went through a lot of that startup experience that you described. We have that common background. In technology, that is the key. You described it perfectly, Crossing the Chasm and there are the early adopters. You got to scale quickly from a sales and revenue standpoint so that you can make it a software business. Not all of our readers are in software. Let’s back off of the technology-specific experience that you and I could talk about for days and talk specifically about the company-building things that you had to do.

You mentioned using a methodology. EOS has been mentioned before on this show. We do something similar as well. Regardless of the name of the methodology or the approach, what were some of the key elements that helped you guys get aligned, be focused and do some of the business-building things that would enable you to scale?

There are a couple of other frameworks like this. I’ve heard that Rockefeller’s framework is similar and others. What I liked about EOS is that you have these rocks, which are goals. You can have up to three rocks. That’s what they say per quarter, which is significant improvement and processing capabilities that an individual or group of individuals can drive. Once we laid that out, we rolled those as a function or extension of the overall company goals, which were revenue. In our case in a tech world, it’s retention on a subscription basis.

Most of the other companies are going to be either revenue or customer success of some sort, either through retention or a repeat of business over a period of time. I used to work for GE. We used to do it quite a bit. Jack Welch on the top would say, “Here are the metrics.” Everyone below will have metrics that rolled up to Jack Welch. We did something of that and said, “Here are the three top KPIs that we are going to run. Let’s divide everything down.”

As we divided it out, individual folks are very focused on the number of driven goals. Each of the metrics had a targeted goal that they were able to achieve. Of the 3 rocks, we would have 2 rocks. In the third one, we have six values in our company and one of them is to be a ferocious learner. I’m a firm believer. I have at least 78 courses signed up on Coursera every time. I am constantly learning. I wanted that to happen with the team too.

One of the goals was that every quarter they were going to learn one thing and that was part of their goals. Combined with learning, we grew the overall capability of the team and then with the goals, we were able to drive metrics to achieve them. Since then, we have changed a little bit of learning and it’s much more improvement projects that they’re executing. That’s from an EOS standpoint.

From a business-building standpoint, any business which is starting would’ve seen the same. First, the salesperson is generating the lead, responding to the lead or nurturing the lead, closing the deal and doing even the account management. You grow and then split it. You have a team that does the insight sales, which is nurturing the lead to a qualification. Sales comes in and then there’s the account management and CSM team. It goes around that point.

A couple of years back, we started that journey. We started looking at where deals were getting stuck. We started to break that role to say we can have two people do pieces of it and then grow it. That works. Our sales team is broken into insight, as well as sales, which closes the deal. We are building out an outbound sales strategy. As we go through, I feel that it’ll get more and more broken down into smaller pieces and each team has its individual goal to drive the overall numbers.

Let me highlight a few things that you said because they’re super important. These specific methodologies that you use, whether it’s EOS or the Scaling Up, the Rockefeller Habits thing from Verne Harnish or even our Elite Business Growth Method, whatever the method, the core tenets are the same. We need to be aligned on the critical few things that we all need to move forward together in one unified motion.

If we’re not taking targeted, coordinated action as a team, we’re acting inefficiently. You stay in whack-a-mole land. You describe that perfectly. In startup mode, it’s like we whack one mole down, a couple more come up and we’re whacking and whacking. What you guys did was take it a very important step forward as a company. You got intentional on, “Here are the key three things we’re going to focus on in the quarter.” We call them quarterly priorities. Other people call them rocks, whatever they’re called. We got to say no to lots of things to say yes powerfully to a few.

You guys learned that lesson, which is fantastic. You brought in some of your GE experience where you said organizing work. That’s what we’re doing. Organizing work comes down to being clear at the top about the key focus areas and how we’re going to measure those. It’s a cascading exercise. We cascade objectives down so that everyone in the company knows their specific role to fit in with what everybody else is doing to achieve the outcome we’re driving as a team. That’s an important thing that I heard as well.

Winning At Problems: Organizing work comes down to being clear at the top about the key focus areas and how we’re going to measure them.

I would distinguish the quarterly priorities or rocks from the day-to-day responsibilities of every role. There’s a longer-term progress thing that you’re balancing with the need for shorter-term operational excellence. That mix can happen if you have the combination of a quarterly planning and execution rhythm and the day-to-day measurement that ladders up to the leader, as you described. I hope I’m summarizing the way that you’re trying to communicate. Does that sound right?

You summarized it well.

We don’t always have very technical CEOs on our show. We’re grateful to have somebody from a tech startup who can tell the way that your mind thinks and the value of ferocious learning. That value is serving your company well. One of the worst things that happen or the struggles that a startup in the tech space will experience is they can quickly grow to a place where they’ve outgrown their team. They were the perfect team at $1 million but they may not know what it looks like at $3 or $10 million. All of a sudden, you outgrow those people and you got to say goodbye to loyal people or you get stuck. That’s painful.

If you are constantly driving, learning and growing for the team, then they might be able to keep up with the pace of the growth of the company and stay around for a longer stint of the journey. I love everything you’ve talked about so far. You snuck into that values conversation. It sounds like you guys did some intentional foundational values work as well. Do you want to share anything about, not necessarily, the detail of those values but why you decided to do that? How you guys came together around that, maybe what it’s done for you as a team?

Part of the EOS was to start with the value system. That started us to lay it out and we had internal conversations quite a bit of it. Some are the key ones. I come from an entrepreneurial background and the way we run the company is very entrepreneurial in nature. We have a very open book across the company. Everyone in the company knows how much revenue there is and how much margin. On a daily basis, there’s an email that goes out.

They’re very well-informed. We review the books with the team so it’s not hidden behind. They participate in it. That’s why the first goal that we have is having entrepreneurial leadership. You’re passionate and experimenting a lot. The other thing that I have done is do two weeks experiment that came out of the world of sprints.

Anyone coming to the team can suggest an idea and we give them two weeks to prove it and the funding for it. If they show progress, then we go another two weeks and so forth. If they don’t show progress, we can come back again but then the funding stops. As long as you’re showing progress, we constantly want them to experiment. We have gotten quite a bit of good results over the years.

The other one is being customer-centric. Every organization has to have that. You need to listen to customers. If an issue from a customer comes in, then everything has to stop until the customers are happy. That’s something we follow. A lot of people are engaged. I talk to customers. A lot of our team members, even the engineering team, are constantly involved in talking to customers. We want to make that part of it. We are trying to improve on it constantly.

Winning At Problems: Every organization has to be customer-centric. You need to listen to the customer.

The other one goes back to hiring. If I find a colleague of mine at a party or someplace, I should run towards him, not away from him. Being fun to work with and having that spirit is key. That’s how we hire when we are interviewing. It’s not just what you know. “Is this person going to be a family member in the long run with us?” Voracious learners are another one.

The last one I put in is we should think about the company. As you grow, you are hiring people and they are very much thinking about their salary and their role. We are saying, “That’s not enough. You need to be thinking about the company. The decisions you make are not just for the role you’re making for the company.” That’s why we have an open book within the company also. Those are the values that we have and we work through each one of them.

I want to point something out for our readers here because they’ve heard several of these interviews where I’ve brought somebody on from the Inc. 5000 list. They’re all probably in that 1 to 3 million range at the time that they got the Inc. 5000 and are still growing from there. What I hear constantly and what I hope my readers are paying attention to is that in every single case, without exception, these companies that are succeeding, yours included, Rajeev, there is a foundation in place culturally. You have spent time being intentional about what it means to be part of the DBSync family. I even heard you use the word family.

This is not just a collection of smart people, although it has to be. It’s a bunch of people who share a common purpose and values. It’s a lot easier to work together but it’s more fun if things flow better. You guys get better results than the competition who hasn’t done this kind of work. I’ve never met you before but by knowing where you’re at on that Inc. 5000 list and seeing you progress as well as you have, I know you’ve figured some of these things out. I can almost predict you’ve done some valuable work. You’ve figured out how to align a team to a common goal and how to do some of this balancing of short-term and long-term objectives. Also, how to hire good people that fit with your culture.

These are very predictable based on the success you’re having. It’s great to hear another version of it coming from you. Thank you for sharing all that you’ve shared so far. As you think about 2019, are there any additional lessons that pop out for you that would help another entrepreneur avoid a pitfall or speed up a learning curve? However you want to look at it, how can we help somebody with your experience?

One of the things is the COVID-19 crisis and managing crisis. Hopefully, we don’t see this again but nonetheless, you will have this crisis. Internally, we have decided that we are going to stay and keep the team together. The motivation and the fear that the team has is quite a bit with all the news, negativity and all these things flowing through. It’s very important for anyone going through this phase to focus on that and get refocused on something that takes their mind off this crisis. They feel that there’s stability, as well as they should feel that there’s work to be done.

In our case, we have taken up improvement projects, like Six Sigma kind of projects, where we have said, “Forget about what the load is for work or not. We have this golden opportunity to improve our product and processes so that we can come out stronger.” Fortunately, we are cashflow positive. A lot of other businesses are struggling but it’s very important to keep the mentality and intensity of your team intact during this phase. Hopefully, we will come out stronger. Keep in mind that people are what makes a company and you have to spend some time with them, making sure that they are involved and progressing. They’re not caught up in this whole chaos that is going on.

Those are very wise words there from a successful leader. Rajeev, you have more technical capability in your little finger than I have in my whole body when it comes to all the technology that you swim in. What I love about what you said is it had nothing to do with your expertise or deep industry knowledge. Any of the things that a lot of people would focus on around what you know, what you shared, had everything to do about leadership.

Whether or not you had some natural leadership capabilities, you’ve grown yourself in a way to not only be a capable technical leader but a great people leader who understands whether we’re in times of crisis or not. The most important asset and the leverageable resource you have in your toolbox is the group of people that are on the team. I love the way you described how you are trying to help ease their concerns and relieve their fear during this time of uncertainty.

I believe you know that there’s no way they can productively engage in the problem-solving that you need them to engage in for your company if they’re stuck on fear, uncertainty and doubt. Great work. I love everything that you were able to share with our readers. If people want to learn more about DBSync or connect with you in some way, what would be the best way for them to find out more about your services or learn about you? Where would they go?

MyDBSync.com is our website. It’s pretty rich with a lot of content. We have a great community to join in. There are a lot of free trials. You can try it out. If you want to reach me, my email is Rajeev.Gupta@MyDBSync.com. Hit me on LinkedIn. Search Rajeev Gupta – DBSync. I should be the first one on it and message me.

Rajeev, you are so generous in giving us some of your time. Thank you for sharing your many wonderful lessons about moving from not just a technical expert but an extremely great technical mind to a leader of people and a growing organization. My hat is off to you. Well done.

Thank you, Brett.

Everybody, make sure you check out MyDBSync.com to learn more about Rajeev Gupta’s company and his team. It’s great stuff they’re doing but more importantly, go back and read some of the lessons that he shared. We do our best every week to bring you real stories from real business owners. Occasionally, we throw in an expert or I’ll give a little solo cast of some sort but we continue to bring you the lessons that you need to be able to grow your seven-figure business. Thanks for reading. Please review, rate and share this show with others. Stay with us for future interviews. Thanks, everyone.

Important Links

• DBSync
• Avankia
• TargetRecruit
• Salesforce.com
• Infusionsoft
• QuickBooks
• Rocket Fuel
• Crossing the Chasm
• EOS
• Scaling Up
• Elite Business Growth Method
• Rajeev.Gupta@MyDBSync.com
• Rajeev Gupta – DBSync – LinkedIn