Thought Leaders in Cloud Computing: Sash Sunkara, CEO of Rackware (Part 1)

A deep-dive into cloud infrastructure.

Sramana Mitra: Let’s start by introducing our audience to yourself as well as to Rackware.

Sash Sunkara: I’m the CEO and Founder of Rackware. My Co-Founder is Todd Matters. He’s my Chief Architect. We started Rackware in 2009. Rackware is a cloud management platform specifically targeted at mid-size to larger enterprises. We have a cloud management suite of products. We started off migrating applications into a variety of private and public clouds. Soon after, we introduced disaster recovery in the cloud. >>>

Building a Mid-Market Security SaaS Company from Canada: J. Paul Haynes, CEO of eSentire (Part 7)

Sramana Mitra: When you looked at your business through that lens, what were some of the salient points?

J. Paul Haynes: Our retention rate was 99%. When I shared that with our next investor, they had never seen anything that high. Our customer acquisition cost was too low. From our perspective, you got to get out in the market. You’re missing opportunities because you’re not spending enough on marketing.

I didn’t really have an appreciation for how well we were performing compared to our peers. Those retention rates were off the charts. I quickly learned that that was a differential thing when you’re raising financing. When I was reviewing these with a much more >>>

Building a Mid-Market Security SaaS Company from Canada: J. Paul Haynes, CEO of eSentire (Part 6)

Sramana Mitra: What was the growth rate from there on? Once you got to building the SaaS business, you zeroed in on the mid-market financial services vertical. You’ve defined your target audience very precisely. You’ve got this whole community of influencers around you. What kind of growth rate were you hitting?

J. Paul Haynes: This is going back a few years. We were probably in the 75% y-o-y range. It was higher in the earlier days. We’re at about 65% right now.

Sramana Mitra: What are some of the other strategic moves that you’ve made in building the business that are >>>

Building a Mid-Market Security SaaS Company from Canada: J. Paul Haynes, CEO of eSentire (Part 5)

Sramana Mitra: How long did it take you to launch the SaaS version of this product? When did you start selling that product?

J. Paul Haynes: A year.

Sramana Mitra: We are talking 2011.

J. Paul Haynes: Yes.

Sramana Mitra: So in 2012, you were a SaaS  company? >>>

Building a Mid-Market Security SaaS Company from Canada: J. Paul Haynes, CEO of eSentire (Part 4)

Sramana Mitra: Where did you raise money? You said you worked with some investors that you had prior relationships with and who wanted to get in early. Are these Canadian investors?

J. Paul Haynes: The first investor was Venture Link, which was Toronto-based. They came in fairly early. They have another affiliate firm. The government put a program in place that encourages venture investment. We were able to take advantage of an interest-free loan that was non-dilutive. There’s a window of eligibility that we just happened to take advantage of. The first round was in June of 2011.

Sramana Mitra: You said something which is a bit unusual. I want to explain that to the people who are reading >>>

Building a Mid-Market Security SaaS Company from Canada: J. Paul Haynes, CEO of eSentire (Part 3)

Sramana Mitra: For the Series A investors, what did you tell them you were going to do? What problem were you going to solve?

J. Paul Haynes: I described to them the problem of solving cyber security in the mid-market. Everybody in the industry at that time appeared to be focused on the enterprise. We just have to sell to 50 of the Fortune 500 and the company is exit-ready is the standard business plan I was later told. The thing that drew them our way is we said, “That’s not who we’re selling to. Instead of the Fortune 500, we’re going after the 10,000 mid-sized enterprises in America and other parts of the world that have the same >>>

Building a Mid-Market Security SaaS Company from Canada: J. Paul Haynes, CEO of eSentire (Part 2)

Sramana Mitra: Before all this, it sounds like you started doing companies in ’76. I don’t think we have enough time to cover that long a story. It sounds like you have a background in enterprise security software. Could you give us a little bit of an idea about what you did before?

J. Paul Haynes: I did a Bachelors in Engineering and a Master’s in SCADA. During that, I started my first business. Upon finishing my Master’s, I already had a full customer roster working in the utility energy market. I basically went right into a job that I created for myself. I haven’t looked back. I think I graduated in 1991 from the Master’s. >>>

Building a Mid-Market Security SaaS Company from Canada: J. Paul Haynes, CEO of eSentire (Part 1)

If you haven’t already, please study our Bootstrapping Course and Investor Introductions page. 

There are opportunities of building cloud businesses focused on mid-market customers, and many entrepreneurs are leveraging those to build compelling businesses. eSentire’s strategy is one worth looking at closely.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

J. Paul Haynes: I was born in Toronto. I grew up in a suburb of Toronto called Oakville. I grew up in a family of people studying >>>