Misconceptions in Tech: Career Insights from VP of Sales at Venture-backed Startup.
I had the pleasure of interviewing Riley Juliar, an enterprise sales leader with over a decade of tech sales experience whose work helped contribute to two liquidity events, first an IPO and acquisition at HomeAway, and later an IPO at SurveyMonkey. He’s since led sales at a number of venture-backed startups and is currently Vice President of Sales at Dray Alliance, a technology platform for containerized cargo in the supply chain. We caught up with Riley about some of the misconceptions he’s experienced in his tech sales journey.
How did you break into a career in tech sales?
While the SDR role has exploded in recent years as a catalyst to tech sales, I took another route. I first approached a tech company that was hiring highly transactional, inside salespeople. They were looking for people who had the energy to handle a high volume of opportunities on very short sales cycles. These sales jobs still exist today where you may not be selling enterprise software in a purely B2B setting, but perhaps you’re increasing participation in a marketplace or selling small subscriptions or services. Many of these roles don’t require any closing experience, but they can be a good introduction into tech sales. I then earned the confidence to transition to enterprise sales motions that eventually evolved into strategic software sales. If you’re trying to break into tech sales, you might find that approach to be a less crowded path than fighting to be one of the top 10% SDRs who get promoted into closing roles.
What has been your biggest challenge in your sales career?
My biggest challenge has been learning to become an effective sales leader after being a top seller. Too often companies promote individual contributors into sales managers under the misguided assumption that the newly minted managers will be able to effectively transfer their skills onto the teams they manage.
When I first became a manager, I did what I knew to do: close deals. My team performed well enough for my company to IPO, but I was burnt out and unhappy. At one point, I recall my best salesperson turning in his notice because he no longer felt empowered to close his own deals without my intervention. I then began to resent my role as a leader and miss my former role as an individual seller. This type of dynamic is entirely too common among tech sales teams, especially in a startup environment.
I’ve since learned how to become an effective sales leader, but that transition was as jolting as learning how to write with a non-dominant hand. Similar to learning how to parent, it required a tremendous amount of restraint to resist the urge to over-support, and even on occasion, amenability to let my team fail in a controlled setting in favor of cultivating rich learning. It can be extremely rewarding and lead to a fruitful career, but there are a meaningful amount of sales leaders who quickly return to their former roles as individual sellers, and there’s nothing wrong with that.
What is it that most excites you about sales?
I get really excited when I see people hack the system. Sales is one of those trades where you encounter many top performers who come from non-traditional backgrounds. I once hired an SDR from an improv class who was waiting tables. That person now makes over a million dollars a year selling enterprise software to strategic accounts, and they did that in the span of three years. I majored in philosophy and dropped out of an MBA. It fascinates me how we’ve created a traditional education system that is supposed to teach us how to become productive employees in the workforce, yet conventional paths can be circumvented so easily simply by learning how to create and convey value by other means outside of traditional education. Seeing a humanities major return from a multi-year backpacking trip and quickly earn seven figures in tech sales will make anybody question the systems we were all told to participate in. There are certainly many examples to the contrary, but there are too many other examples of this kind to ignore, and I find that exciting!
If you had to share, “words of wisdom,” with a new Sales Rep who’s about to start their career, what would they be?
If you don’t know what you’re aiming at, you’re going to miss every time. You’re about to join a career of enduring accountability. We are accountable to ourselves, our families, fellow sellers, cross-functional colleagues, customers, board members, and investors. What being accountable means is not winning every time. Everybody has a down quarter. It means being able to identify what’s breaking so that you can fix it or ask for help. There’s no way to do that without a plan.
So your first step should be getting very clear with yourself on what level of input is going to be required to achieve your desired level of output. Regardless of what you’re selling or how much it costs, a great place to start is your expected win rate multiplied by your expected deal size multiplied by the number of qualified opportunities you need to support your goal. You can distill these variables down further, but the end result will be a light that shines brightly upon all of the dependencies you are relying on in order to achieve your goal.
A good sales leader will test for this by asking how many opportunities you need to meet your goal this year, and what assumptions you’re making. If you can’t answer that question quickly in an informed manner, then that is an indicator that your strategy to execute could at best limited to trying really hard and seeing what happens. That works… until it doesn’t. The biggest reason we are employed is to generate meaningful revenue for the business. This is how we support our families and how we ensure that many other people also get to keep their jobs. We don’t always succeed, but it needs to be taken very seriously. It’s never okay to miss if there was never a plan to hit.
How can our readers follow you on social media?
I’m far from a “salesfluencer”, but always open to networking and participating in interesting projects. I hope that you connect with me at https://www.linkedin.com/in/rileyjuliar/
