Episode Twenty-Six

The Surprising Truth Behind Square’s Success: A Rare Combo of New Tech and Old School Sales Tactics

Guest: Tom Hanrahan, Head of SMB Sales at Square

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About This Episode


Square: It’s led by one of the great CEOs of our time, Jack Dorsey. On the surface, it can be easy to think Square’s moving at lightning speed, constantly creating technology that’s changing their industry.

You’d be totally correct.

But you’d also be right if you thought that they had an old-school sales mentality:  boots-on-the-ground, literally knocking-on-doors sales tactics. Somehow, they’ve combined both.

We know because we talked to the Head of SMB Sales, Tom Hanrahan. This guy’s an anomaly himself.

He started his sales career selling uniforms with Aramark before moving to NYC to work for LivingSocial as a Sales Leader. Next up was Seattle, with a small company named Amazon. Of course, he had a stint in Silicon Valley. But his next move was unexpected: He took up the Head of SMB Sales position for Square and moved to St. Louis.

Tom came on our Sales Engagement Podcast to share how Square is not only pushing the envelope in POS and credit card processing, but it’s revolutionizing every sales tactic, by inventing new ones and combining old ones.

Their sales teams borrow from every category but fit in none.

You have to check this out.

Traditional + Radical = Innovative Sales Tactics

From our interview, I can tell you that everything Square does, at least on the sales side, seems to be a rare combination of Silicon Valley progressivism with Middle America tradition.

It’s difficult to wrap your head around that — I know. So let’s break it down into three categories. After all, it’s not every day you can commandeer sales strategy and tactics from a company led by the Jack Dorsey.

Organizational Setup — St. Louis 9-to-5ers Meet Silicon Valley Boss

To start with, let’s check out the high-level of the sales team.

New School: Tom is the Head of SMB Sales. He’s lived in all the traditional tech cities: San Francisco, Seattle, NYC. He brings with him experience from plenty of the big names (Amazon, LivingSocial, etc.). He took off from the West Coast to lead the East Coast sales team in 2016.

As the sales team has grown the last several years he enables his team with the Challenger Sale, Objection training, and new certifications that are difficult to pass.

Old School: On the flip side, Tom’s office is in St. Louis, and that’s no accident. Square put an office there specifically because the talent pool was incredible — the city is full of people who show up ten minutes early, and leave at 5:30: sales types with old-fashioned work ethic, know how to handle typical sales objections, and have all the soft skills necessary for an SDR, BDR, or AE position.

His Sales Team Is Made Up of Fast-Movers and Dedicated Individual Contributors

New School: In a company like Square, they have exactly what you might expect: ambitious upstarts wanting to develop their career rapidly.

Tom mentioned one person on his sales team who came up from Support — he was the kid with the backward hat that Tom wasn’t too sure about until his Support manager told Tom “This kid’s going places.”

On the previous manager’s recommendation, Tom put him in a sales role, and within two years, he’s been promoted twice, is fast-tracked to a manager position, and has nearly tripled his income.

Old School: Tom also ensures that his team isn’t made up of individuals who want a promotion every 6-months or they’re gone (something very typical in Silicon Valley).

This goes back to the choice to open an office in St. Louis. Tom is proud to say that he has a good base of individuals who love their individual contributor position, and are dedicated to honing their craft and really developing within that position.

New Tech, Old School Sales Tactics

When it comes to the iteration of new products, and how they sell that product, it’s old meets new.

New School: Tom was stoked to talk about one of their newest products — Square Terminal. It’s an integrated payment processor with a touchscreen. As soon as it’s delivered, it has a full charge, so you literally push the only button on the device, and take payments immediately. Typical per Square, it’s rather revolutionary.

Sales Tactics Tom Hanrahan Square

Old School: But how they’re selling Terminal is about as traditional as it gets: Tom has his NYC team literally knock on doors to show off the new product to Mom-and-Pop stores.

Yeah, we know: It’s a pretty radical concept, combining these old-school American values with big tech changes.

But it gets you thinking — What ways can all of us build up our sales teams with all the right pieces, re-using the old tactics that work, developing new strategies, all in an effort to create something truly innovative?

This post is based on a podcast interview with Tom Hanrahan. To hear this episode, and many more like it, you can subscribe to The Sales Engagement Podcast.

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About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find an energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

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