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PODCAST 140: Habits of a Bootstrap CEO: Depth Not Breadth with Zak Hemraj

If you missed episode 139, check it out here: The Science of Becoming a Better Sales Leader with Luke Rogers

What You’ll Learn

  • Bootstrap companies deserve massive respect
  • 40% of revenue is impacted by the RFP process
  • The pandemic has caused increased scrutiny on companies
  • Bootstrap habits mean structuring your day for both productivity and peace

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Show Agenda and Timestamps

  1. Show Introduction [00:10]
  2. About Zak Hemraj & Loopio [2:18]
  3. Why Bootstrap [07:31]
  4. Let’s Talk About RFPs [12:59]
  5. Habits of a Bootstrap CEO [22:25
  6. Time to Pay It Forward [29:27]
  7. Sam’s Corner [33:01]

Show Introduction [00:10]

Sam Jacobs: Hey everybody, it’s Sam Jacobs. Welcome to the Sales Hacker Podcast. Today on the show we’re incredibly excited to have Zak Hemraj, CEO and co-founder of Loopio. Loopio is an RFP response software. RFPs are something you need to get good at. They’re something you need to figure out how to answer. If you’re at a smaller company, you need every advantage you can get. We’re excited to have this conversation.

Now, before we bring you this conversation, we want to thank our sponsors. Our first sponsor is 6sense. Salespeople are often wasting time fumbling around with junk leads, static lists, and haphazardly reaching out to accounts they aren’t yet ready to close. The 6sense account engagement platform uncovers and analyzes buyer intent at scale, identifying prospects who are in the market for your solution and providing salespeople like you with the insight to create highly relevant messaging, generate more opportunities, increase deal size, and get into opportunities before your competition with 6sense.

Our second sponsor is Outreach, the number one sales engagement platform. Outreach revolutionizes customer engagement by moving away from solid conversations to a streamlined and customer-centric journey. Leveraging the next generation of artificial intelligence, the platform allows sales reps to deliver consistent, relevant, and responsible communication for each prospect every time, enabling personalization at scale previously unthinkable. Check out outreach.io for more information.

And finally, we turned Sales Hacker into a community. Rather than just reading or listening, you can now ask questions and get amazing thoughtful answers from the world’s B2B sales professionals who’ve been there before, plus you can share your experience with others. Go to saleshacker.com and create your profile today.

Now, without further ado, let’s listen to this interview with Zak Hemraj.

About Zak Hemraj & Loopio [2:18]

Sam Jacobs: Hey everybody, it’s Sam Jacobs. Welcome to the Sales Hacker Podcast. Today we are honored and excited to have on the show Zak Hemraj. Zak is the co-founder and CEO of Loopio, a Toronto-based software company that streamlines the RFP process for companies like IBM and DocuSign. Before Loopio, Zak worked as a software engineer, turned a sales engineer where he had firsthand experience responding to RFPs at a fast-growing SaaS company. After this experience, Zak took the entrepreneurial plunge in 2014. He co-founded Loopio with his closest friends, Matt York and Jafar Owainati. Today Loopio serves more than 850 world-leading organizations ranked 13th on the 2019 Deloitte Technology Fast 50 List and were selected as one of LinkedIn’s top startups in Canada two years in a row. Zak, welcome to the show.

Zak Hemraj: It’s a pleasure to be here, Sam, and thank you for the kind intro.

Sam Jacobs: We’d like to start with your baseball card. You’re the CEO and co-founder of Loopio. Tell us what is Loopio in your words?

Zak Hemraj: Sure. We are an RFP response software platform. There’s two sides to the RFP equation. There’s the people that are buying things and people that are selling things. We cater to the sellers, so sales teams and adjacent teams, really helping them respond to RFPs at scale, streamlining all the work around how they talk about their products and services, how they deal with all the different RFP requirements, and really orchestrating the end-to-end response process, and then gaining insights from that. At the end of the day, it’s all about removing obstacles so that you could sell more and grow faster.

Sam Jacobs: The company was founded in 2014. Give us a little bit of the background on how you and your two co-founders decided to start the company.

Zak Hemraj: It’s like most entrepreneurial stories, and it starts with experience. I was previously working in a past life as a sales engineer. A lot of my work ended up being just this, responding to RFPs, security questionnaires, online assessments, just to remove obstacles and reassure the teams that we were selling to that we were a legitimate company. That’s where it first started, experiencing it firsthand.

Back in 2014, me and my two co-founders, Matt and Jafar, we just started getting to work. Matt and I were still fairly technical, and so, we were able to build the first version of the product. Jafar got to work and started pounding the phones. We just leveraged our networks and we got some initial sales off the ground and just started bootstrapping the company from the early days. I wish we had some profound vision at the beginning, but it was really, “Let’s just make it easier for companies to respond to RFPs.” Then we got to work.

Why Bootstrap [07:31]

Sam Jacobs: There’s a few different reasons why companies and founders bootstrap. Tell us about why you decided to bootstrap.

Zak Hemraj: In the beginning, it was, “Let’s just get started and we may fundraise.” So we were always having discussions in the early days. As we started to get some initial traction, it became clear that we could bootstrap it at least for a little while. Why we became more intentional was we started to realize that we could hang on to more equity as founders. We could control our own destiny.

Upon reflection, being bootstrapped for the first three years of our business really helped us build that culture of customer centricity and really being disciplined about how we made investments, making sure that every piece of software we wrote, everything we put on the website was adding value. We were never shy about the fact that we may fundraise one day when the timing was right, and that’s what we did. I think you’ve just proven this, and I don’t know if it’s an adage. A lot of people talk about, and especially in SaaS cloud land, how markets are way bigger sometimes than at first they appear.

People didn’t understand how big the market opportunity was. But it was also that it isn’t the sexiest problem in the world. So those two things combined definitely caused this cloud of perception that we weren’t worthy. We started to hit scale, a few hundred customers, and it became obvious to everyone. But we always believed. Again, we’ve experienced the pain firsthand. If you just build a company with that mindset of just adding real value for customers and solving real problems, eventually good things happen.

Sam Jacobs: So, just closing the loop on this line of questioning, what was the catalyst for when you did decide to raise money?

Zak Hemraj: It wasn’t an overnight process, Sam. I think, for us, it was a two to three-year process of building relationships to investors. The less you want the money, the more attractive you become. It was around 2017 where it became clear. We reached the revenue scale of what most series A companies raise at, which was around a few million in ARR, a few hundred customers. It became clear that there was repeatability in the problem.

The other thing was that we started to notice the competitive landscape starting to heat up quite a bit. So with all of those things coming to a head at the same time, it just felt like the right time. And then we were able, because of the relationships that we had built over the course of years of the investors, that we were able to mobilize fairly quickly.

Let’s Talk About RFPs [12:59]

Sam Jacobs: Let’s talk about RFPs because they are pretty intimidating. How easy is it for fast-growing companies like Loopio that are younger in age, how easy is it for them to win RFPs with larger, more sophisticated enterprises?

Zak Hemraj: Maybe I could even take a step back. What is an RFP in the world of enterprise? RFPs can take on many shapes and forms, and then we often abuse the term. It is not always just a request for proposal. It could be a request for information. It could be a security assessment. It could be 10 questions in an email. It could be an online form that you have to fill out. We put that all under the blanket of RFP. At the end of the day, it is buyer diligence. It is this big buyer that’s trying to evaluate against some criteria.

We went through that process as Loopio in building the company. We had to respond to RFPs in showing that we were a legitimate organization. That’s one area that you have complete control over, that you could showcase yourself as a buttoned up professional company that is thoughtful and responsive and a strategic partner. It’s absolutely possible. You’re definitely going to change over time as you get more capabilities.

One thing that we can definitely dive into as well is through the world of 2020 and COVID, the way that buyers are scrutinizing things are also changing and evolving, and we’re seeing higher forms of RFPs and diligence in sales cycles as well. Anecdotally or based qualitatively in my discussions with customers and with the market, it’s because of COVID and the capital preservation that most companies have now had to take on, it’s just there’s a lot more scrutiny in every single purchase, like CFOs are getting involved.

Salespeople that are listening to this podcast, you’ve probably seen that your enterprise sales cycles are slowing down. The reason for that is there’s just a lot more scrutiny. And so, we’re seeing an uptick in understanding vendors’ approach to business continuity, their security certifications, how they actually plan on delivering value. And then what that translates to is activities like RFPs and in similar questionnaires that are showing up, especially in enterprise sales cycles. But not limited to just enterprise. It goes down to mid-market and SMB as well. That’s a trend that we have seen across all industries, is just more buyer diligence, which means more questionnaires, unfortunately, for salespeople.

Sam Jacobs: What advice do you give to companies in terms of qualifying that communication in the right way to allocate the right amount of resources? Do you give advice to your customers in terms of how to manage the process beyond simply responding to it promptly?

Zak Hemraj: The sales professionals that are responding to RFPs, don’t be afraid to ask questions. That’s one thing that I see all the time, even when we think about our own team here internally, is that you receive an RFP and it seems like a very formal, buttoned up mechanical exercise. A lot of times the buyer is willing to shed a light on a lot more information. Different industries have different regulatory requirements and restrictions around RFPs. But I would say never be afraid to try to make things into a conversation if you can.

That would be my one general advice, is asking questions, making into a conversation. If I look at the data, Sam, like when we did the last benchmark study, 40% of companies and sales teams, 40% of their revenue is flowing through RFP activity.

Sam Jacobs: You’ve talked about how you need to turn RFPs from an obstacle into an opportunity. Walk us through your perspective on how companies can do that.

Zak Hemraj: The first thing is building on what I just said around having a process, even if it’s a spreadsheet, keeping track of what RFPs you’re responding to and having some kind of light project management around that. A lot of that’s going to come down to how fast you can respond and measure it.

Step two is about having some sort of content repository. At the end of the day, RFP responses are going to be a culmination of how you talk about your products and services. So having a very curated up-to-date content repository of content snippets that can be stitched together for different purposes is a critical component of this. Then from there, if you do leverage a platform like Loopio or something else, you’ve got to think about automation, how much can you automate so that your teams can actually focus on the work that really matters around differentiation and then dealing with all the different documents and formatting.

Then I would say that the last step of maturity in this process is really getting to a point where everything is on rail so that you can start pulling away insights from the volume of RFPs. We have a customer that responds to six to 800 RFPs a year through Loopio. Each of those activities, you can gain insight and pull away takeaways from that. This process probably sounds familiar because it’s the same thing in any system that you roll out, is you want to get a process to a point where you can start pulling away tangible insights from it. So that’s what we try to do with our clients.

Habits of a Bootstrap CEO [22:25]

Sam Jacobs: For you as the CEO, what’s changed? What are the things that you didn’t expect when you started the company over six years ago?

Zak Hemraj: I’m always surprised year after year when we do our strategic planning, how much more we want to focus every year and how big the market opportunity really is. You start realizing, and I’ve noticed this in my personal life too, is depth over breadth. Almost getting to the point where we had to look ourselves in the mirror and say, “Hey, let’s be unapologetic about the fact that we are RFP response software and that’s what we do.

The constant desire to focus and focus more. That always surprises me how much more opportunity there is when you subtract things and focus in more. That pattern keeps showing up day in and day out. Yeah. So that’s on the company side.

People continue to amaze me of what can happen when you hire the right people and just get out of the way and support them rather than direct them. That continues to surprise me on a regular basis as well. I’m very early on my CEO journey as well, learning a lot by the day. But yeah, people are the main thing, just understanding that that’s at the center of it all.

The thing that has noticeably become different year over year as the company has scaled is the ups and downs of the emotional roller coaster are much more vast and much sharper, in a sense of how fast things can go from feeling like you’re on top of the world to the world is falling apart, is much deeper. David Cancel talks about this all the time, of the number one thing you have to do as a CEO and as an entrepreneur is understanding how to tame this emotional roller coaster and trying to stay steady through it all. That’s something that I’ve been trying to work on.

Sam Jacobs: What is it driving the emotional ups and downs, given that objectively you’ve already succeeded in many ways?

Zak Hemraj: Success is relative and every company looks perfect from the outside in. You only see the company all buttoned up and then out the door. But every company internally has your own stresses and ups and downs.

If 2020 has taught us anything, it’s how fast things can change. The other thing is that the ripple effects in a larger company, like things that happen at the top and as they ripple across an entire organization, are just amplified the bigger the company gets. So there’s just more opportunities for things to throw you off your course, the bigger a company gets.

Ultimately, your team loyalty and team engagement in the culture that really matters is going to be tested during a crisis. I’ve never experienced true crisis management as a leader before this. Going through that, just you feel a sense of pride of how the team stepped up. I would say that everything we did for the six years leading into COVID was preparation for this moment, because by the time it hit, it was too late to really shift in a meaningful way. Let’s see, who you are is going to be what took you forward.

Time to Pay It Forward [29:27]

Sam Jacobs: When you think about people or ideas that you want the audience to know about, what comes to mind?

Zak Hemraj: David Cancel is definitely somebody I’ve been following and love. I’ll just speak to what I’m reading right now. I’m reading James Clear, Atomic Habits. In the book, he talks a lot about just how our success is the compound interest of our habits.

Through this year specifically, one of the habits I picked up was doing very structured, weekly reflections. It’s almost like professional journaling in a way. So a Friday or Saturday morning coffee,, I’ll just sit down and go through the same questions of looking back on the week, eventually leading to like, “What are the top three to five priorities for next week? And what’s your action plan to get them done?”

Get in touch with Zak on LinkedIn or by email.

Sam’s Corner [33:01]

Sam Jacobs: Hi folks. Sam’s Corner. Great conversation with Zak Hemraj. I always respect bootstrap companies. You don’t want to just show up and be transactional with anybody, in any conversation, in any context. That’s not how it works. Be aligned, which means provide data, build a relationship over time.

Now, as it comes to RFPs, I was just interested by the statistic. 40% of revenue is impacted by the RFP process. So it probably means that’s something that you should be thinking about and taking time to do. There’s increased scrutiny on companies, given everything that’s going on with the pandemic. That’s point number two. Point number three is just atomic habits. We’re all thinking about, how do we structure our day for maximum productivity and also for maximum peace and happiness?

Don’t miss episode 141!

I hope you enjoyed the show. Before we go, let’s thank our sponsors. The first is 6sense. The 6sense account engagement platform uncovers and analyzes buyer intent at scale, identifying prospects who are in the market for your solution and providing salespeople like you with the insight to create highly relevant messaging. Go to.

Our second sponsor is Outreach. Outreach is the number one sales engagement platform for the modern sales organization. If you want to get a sneak peek into how Outreach does things go to outreach.io/saleshacker for a four-minute sneak peek, order requested demo, and to get an inside view on how Outreach brings efficiency, visibility, and versatility to modern sales teams.

If you want to reach out to me, you can find me on LinkedIn or email. I’ve enjoyed this opportunity to speak with you. If you haven’t rated the show, please give us five stars on the iTunes rating system so that we can remain in business and continue to bring you this show.

As always, thanks so much for listening, I’ll talk to you next time.

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