Interview of Cailen D’Sa, Front’s Head of Sales

By on June 27th, 2016


Cailen D’Sa joined Front almost one year ago. Originally from Canada, his family moved to Cupertino when he was 7. He graduated from San Jose State University with a Major in Business. He was the first sales hire at both and Dropbox. He’s now Head of Sales at Front. He was featured on The Twenty Minute VC a few hours ago, and you can read my interview with him here!


Your career started in sales at, back in 2007 when you were fresh out of college. How did that happen?


It was the most random luck! At the time, there were only two big things for job hunting: Monster & CraigsList., because it was the name at the time, had a listing on CraigsList that said “9-person startup looking for Account Executive”. I had no idea what an Account Executive was, but the words sounded important, so I replied!


Did you know anything about sales at the time?


I knew how to sell. In college, I was doing tutoring on the side as a part-time job. I started as a tutor, making $90 an hour! The pay was so good that many of my friends wanted to join, to the point where we didn’t have enough lessons to give: my job quickly turned into finding more and more gigs for them. I was selling the lessons they would teach.


I thought about running it full time after college, but the competition was tough, and I was very excited about the tech industry, so I looked for a job instead.


So you knew you wanted a career in sales?


Not really. Before joining Box as Account Executive, I had a competing offer from Cisco as a Marketing Analyst. The pay was double there, but I was really attracted by the people at Box. The founders were my age (making me feel like a total underachiever by the way), we got along really well and I liked the challenge. My father and brother pushed me to go for the riskier option, which made it even easier. I do not regret that decision!


In 2007, Box was a barely a company yet. What kind of first job was it?


It was the typical startup. We were working from a loft, there were beds on the floor, the team was 100% male, you get the idea. Box was a highly successful consumer product, with more than 700k signups when I joined. My role was to see how we could turn that into actual sales to established businesses.


In practice, as the first “business” operational hire, I was more of a jack-of-all-trades, and had to figure out a lot of things on my own. For one, there wasn’t as many startups around, so everyone including myself was pretty uneducated about the actual content and expectations for such a job. There were also way less tools to help you do your job: no Pipedrive, no PersistIQ, no Clearbit, etc. You had a phone line, an email address, and a account.


It was all trial-by-fire, talking to as many customers as I could. It helped build the kind of resilience you need if you want to stay in sales for some time. But in retrospect, I would have loved to find a mentor there to show me the ropes. I’m a big fan of learning by doing, but shadowing more experienced salespeople is the quickest way for a junior to learn. It wasn’t an option for me at the time, but since then I’ve always made sure that all the people I hire get to see how the job is done by someone more experienced.


The other thing I learned from that time is how important it is to be aware of your product-market fit, and of what’s preventing you from moving up market. The job of the early sales team is to feed this info back into the product, so the product can come back later to close the sale. Too often in B2B startups, there is a big divide between the sales team and the product team, and many cycles are wasted because the information doesn’t flow from one to the other.


Then you joined another startup in the same space: Dropbox. Didn’t it feel like doing the same thing over again?


My initial role at Dropbox was similar, it’s true, but the two companies were very different. I see how close they look on paper, but at the time, Dropbox was exclusively focused on B2C, the company was 100% engineers (and there were a lot of them), and last but not least, the companies had different visions of the future. Box was very bullish on the “browsers will be the next OS” vision, and they weren’t alone in that: these were the heydays of Chromebooks, for example. Dropbox came from a less enthusiastic place: people knew file systems, so Dropbox had to be built inside their file system. The web version was a nice addition, but the core product was installed on the user’s desktop.


That being said, my task was again to build the sales process. We had a big queue of people expecting our B2B product, and we were artificially limiting who could get in. I rapidly reached $10k of additional MRR (monthly recurring revenue) per month, at which point we decided we had enough data to build a team. We hired roughly two Account Execs for each Customer Success representative.


Dropbox had a “mature” product by then, why did it take so long to build the sales team?


When you scale a sales team at a company like Dropbox, you don’t do it layer by layer, with twenty Account Executives first, then move to hire twenty Customer Success reps, etc. You have to do it gradually because everybody work hand-in-hand. This is how you learn what kind of deals you can expect, whether the deals are more transactional or consultative, and what kind of customers you can close.


If I had one big learning to share from my time in sales at Dropbox, it’s that in SaaS, there is no such a thing as a purely transactional deal. The best deals always take time. Sometimes you have to accept a smaller volume upfront and continue to work the relationship; you have to see the potential down the line more than the payout from the first closed deal. This is when post-sales help: really big deals cannot be pulled off by one man alone, it has to be a team effort.


Your role changed over time Dropbox. Why did you move away from sales?


My strength is in building things, more than growing them. When I joined Dropbox, the sales process had to be built, but after the Series B the foundation was laid. We were confident that each new hire could bring in enough revenue to make it profitable. The next thing to build was the hiring process to actually make these hires, and that’s how I transitioned to recruiting.


I’m really glad that I did this stint in HR. It made me realize that, once a company is confident enough about what they’re building and selling, the most impactful thing you can do is bring in great people to maintain your leadership. The most important bit of advice I can give about that is: hire high ceiling people, and make them grow. Startups are all about learning from your mistakes, and it’s true at every level, from the product iterations to the cold emails copy. Surprisingly, hiring seasoned superstars from outside can be a bigger gamble than betting on your own people. Don’t underestimate how it can affect your culture, in uncontrolled, harmful ways. That kills companies.


After more than 5 years at Dropbox, why did you decide to join yet another 10-people startup like Front?


Again, it’s because I’m a builder at heart. In a sense, I’m going back to my roots! Front reminds me of Box and Dropbox a lot: a great team with a great product. What they need now is to build a repeatable sales process, and I believe my experience can have a big impact there. The longer I’m here, the bigger the potential I see — and I’ve worked for very ambitious companies… We’ve just raised our Series A last month and are hiring for many different positions, so if you’re interested in SaaS, startups and sales, apply!




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