How to Boost Sales and Productivity by 275% with Zillow’s Tony Small


Zillow’s Tony Small is the general manager for the real estate marketplace’s Premier Agent Business. His organization, which sells advertising to agents, is a primary revenue stream for the company, having grown 70x in the last five years. He leads a diverse team of nearly 400, including salespeople, sales operations, analysts, customer support, billing, and retention. During a recent chat, he shared how he’s used data science to increase sales and productivity by 275%. He also gave his tip for how us non-computer-genius types can introduce similar technology.

You landed in sales somewhat unintentionally.

When I was at Amazon, I managed our B2B business. Part of that scope was that we had to work with a VP of sales there. He had a pretty big challenge with the sales operations team and needed someone willing to roll up his or her sleeves and fix that organization. I was brought in to do it and that’s how I became heavily involved in sales. A friend of a friend then referred me to Zillow for a director of sales strategy and operations role. The rest is history.

Once at Zillow, where did you focus first?

Sales productivity is one of the reasons why Zillow is as successful as it is today. And a lot of the sales efficiency came as a result of putting better sales tools and information at the fingertips of salespeople. For instance, programmatically telling them what to pitch, to which agents, and for which reasons. When we first started, there wasn’t any real process or rigor to what we were doing. Now everything we do is based on data science. And it’s always evolving. What determines who our salespeople should be calling in December of last year is likely different than what it will be in August of this year. We’re also making things better for the customer because they’re not getting bugged about products that they really have no interest in buying.

You took computer science in college. Has that helped with introducing new technology to your team?

It has helped a lot. When I first started there were no developers on my team. Because I have a programming background, I was able to roll up my sleeves and program some of the tools on my own, and take the idea and conception to actual implementation. Now that we’ve significantly evolved, we have developers and staff that do that for me. But having that development background helped a great deal and continues to help.

Any advice for the majority of sales leaders who don’t have a technical background?

A lot of the challenges sales organizations try to address have already been solved many times over by other companies. That’s where these third-party solutions come into play. Generally what we do at Zillow is look at every challenge and do a build versus buy analysis. Typically two-thirds we buy and one-third we build. It’s good to look at places such as Salesforce AppExchange when you have a challenge that, for example, might require a data scientist.

What do you enjoy most about your job?

I used to be in product at Microsoft and Amazon. I would work on something and would maybe see its impact anywhere from three to six to 12 months later. And it could be hard to determine what exactly my role was in that. In sales, you can add a new process and see results within hours. The other thing is that it’s fun to be a part of the main thing that drives a company’s growth, which is revenue. When you’re at the center of the revenue engine, it makes the job really interesting because what you’re doing is so central to the company’s overall success.

What makes your job hard?

In an organization where you have 400 salespeople, there are going to be some ups and downs when it comes to personnel and hiring. For example, a big part of one of our sales roles is cold calling real estate agents, which is a hard job. It would be a misstep to hire people for this and present it as a super fancy job, when in reality, 50% of it is cold calling. To avert that, we’re super transparent about what the job is during the interview process. That’s helped build credibility and increase our retention rate.

How do you boost moral for your team?

We use gamification, such as Hoopla. We have a lot of flat screen TVs throughout each of our offices so every salesperson can view it. For example, if someone makes a sale, all of the screens will flash and it will show a basketball being slam dunked. And then it will show the salesperson’s face, the customer’s name, how much they spent, and any other key stats. It’s connected right to Salesforce, so it takes almost no time to manage or implement it. On the rare occasion the TV screens go down due to a technical glitch, people notice and complain. It’s as if they didn’t get credit for the sale if their face didn’t appear on-screen.

What else have you prioritized?

Culture is really important. We ask our sales professionals and people in the supporting organizations to take a holistic view of what they’re doing for the customers. Because at the end of the day, you need smart people doing smart things. You need to empower them to do that, but also guide them and make sure there is alignment on what the right thing to do is. For example, doing the right thing for the customer might be saying, “Hey, this product really isn’t for you.” And that will benefit you in the long run because you will have a happy customer.

Similar to a walk-up song, do you have a closing song?

“Under Pressure” by Queen. It’s exciting and it has a really good track. It’s a fun song.

If you weren’t in sales …

I would probably be a computer science teacher.

When we first started, there wasn’t any real process or rigor to what we were doing. Now everything we do is based on data science. And it’s always evolving.”

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