Andrew Berger Built Square’s Sales Organization. Here’s His Advice on How to Motivate a Sales Team

In a past life, Andrew Berger was a minor-league baseball pitcher with dreams of the big leagues.

From 2011 to 2013, he spent time in both the Arizona Diamondbacks and San Francisco Giants farm systems and had, as he put it, “a cup of coffee” at the AAA level.

Today, Andrew oversees multiple sales teams at Square.

Andrew has been building out sales teams at Square for the last four years. Not just one sales team, but a bunch of them:

  1. Sales Development: global inbound lead qualification
  2. Business Development: global outbound/BDR program spanning small businesses, mid-market, and enterprise customers
  3. Vertical Sales: full sales-cycle BDRs and AEs
    1. Square for Restaurants
    2. Square for eCommerce
  4. Professional Services: the implementation and organization to onboard new Square users

Square sells to businesses big and small. B2B, B2C, retail, services—you name it, Square has customers. It is the work of the sales team to introduce the company’s solutions to companies of all kinds.

If you’re searching for proven strategies for how to motivate a sales team, there’s a lot to be learned from what Square is doing.

Note: Does your sales team use Slack like Square’s team does? Troops’ Slack-based tools can help your team close more deals. Sign up for a free trial.

How to Motivate a Sales Team

We spoke with Berger and asked him: With years of experience building and leading sales teams, what are your best tips and strategies for how to motivate salespeople?

Here’s what he told us:

1. A Culture That Celebrates Wins

How to motivate a sales team: Celebrate Wins GIF

Besides making sure “wins” are announced to Sales, Berger takes it a step further.

“We get the greatest emails from our customers telling us how Square is really saving them time, or cleaning up their processes,” he told us. “If a BDR rep has 70 out of 75 calls go nowhere, it can really boost morale internally to hear that one of the five that did sign up with us is reaping those economic benefits.”

Square’s sales team uses Slack, including Troops, making it easy for reps to keep up with their tasks and activities in Salesforce.

When a customer email comes through, Berger drops it in a “wins” channel to quickly share them with his team members.

Further, because Berger also works a lot with implementation and product development teams, he also shares these messages with them, too.

“We really use the ins and outs of messaging on Slack for Sales, but most product people don’t want anything to do with the sales side of things,” he explained. “But when we can show them the fruits of their labor by passing along a customer’s positive experience, to tell them, ‘Hey the work you are doing has real-life impact,’ it has a real impact for motivating those teams outside of sales, too.”

2. Creative Spiffs

Berger told us that, particularly for business development reps, getting creative with spiffing has been very successful for salespeople and Square alike.

“We spiff on things that aren’t a part of our day-to-day goals,” he explained. “Goals like adjusted revenue targets are often motivation enough for account executive teams, but for the BDR program, things are a little bit different.”

For example, they spiff the BDRs on utilization of new systems and software.

“Whenever we have a new product launching, new vertical to sell into, or need to test something new, we get the BDR team involved to help achieve that utilization,” he told us.

This way, new processes and products are met with enthusiasm instead of resistance.

3. Flight Vouchers

How to motivate a sales team GIF: Flight Vouchers

“One of the spiffs that has worked best for us is flight vouchers,” Berger said. “It’s simple, but it can be very motivating, especially if the team is heading into a holiday.”

“If we have additional money available for spiffs within a given sales period, we tell the team that the top seller gets a $500 flight voucher.” Sales management will specify that the contest runs only for the next few weeks, and the team really steps up to finish the period strong.

4. Cross-Team Competitions for Paid Fridays Off

Square runs a contest offering a paid Friday off for a pair of sales reps. Implementation specialists, account executives, and business development reps are paired up agnostic of their roles to compete in the contest, which allows for teamwork to reach across team boundaries.

This creates an “all for one and one for all” environment between members of differing teams as they compete to win the contest. This can be particularly motivating in the summer when an extra Friday off means a three-day weekend with a much better chance of good weather.

“But that’s only if the entire team holds up their end of the bargain,” he clarified.

5. Team Location-Based Competitions for “The Sales Shark”

Square has BDR teams working from offices in San Francisco, New York, and St. Louis. To foster a sense of team-building, Square runs contests between the teams at the three locations.

The winning team gains possession of the “Sales Shark,” which Berger will deliver by hand the next time he visits the winning location. “The shark stays until another branch overtakes them,” Berger said.

How to motivate a sales team: the "Sales Shark" that is passed from office to office

6. A Compensation Plan Based on What Reps Can Control

Square’s compensation isn’t based solely on deals closed. Instead, it’s designed to reward reps on what they can control.

For a business development team member, a typical day can include 40 to 50 calls with a goal of 25 to 30 opportunities per month.

Once those opps are created, the BDR often have little or no control over whether the lead turns into a paying customer. For those reasons, BDR reps are compensated on quality lead generation, not whether the AE closes the sale. An AE, by contrast, has a compensation plan that’s more heavily weighted toward deals closed.

Besides reducing the BDRs perceived “failure” rate, Square is creating a more empowering environment for their own salespeople by compensating each of them based on what they can control.

7. Goals Based on the Funnel

With compensation closely tied to outcomes each individual rep can influence, setting and tracking internal goals becomes that much more important.

Berger couldn't disclose the exact goals he gives to the different sales teams, but he did tell us that each salesperson’s goals are closely tied to their specific stage in the funnel.

The BDR team has goals relating to their ability to fill the top of the funnel. The AE team has goals relating to their ability to close opportunities and convert leads into revenue for the company.

8. Tactical, Changeable Goals

Berger stressed that above all, Square takes an open-minded approach to motivational tactics.

All of the teams have goals that are specific to their work. “But all of them have very tactical, changeable goals.”

If an incentive is working, they run with it, expand it, and try new variations to make it perform even better. If a spiff isn’t working, however, they kill it and come up with something different.

Conclusion: Tying Individuals to the Mission

As Berger told us, there is much more to Square these days than just credit card payments.

In 2015, founder Jack Dorsey announced Square was adopting economic empowerment as a new vision for the company.

How to motivate a sales team: Jack Dorsey's tweet- "Square stands for economic empowerment. We stand for financial systems that serve instead of rule. We stand for leveling the playing field."To achieve this mission, Square has launched a series of programs around the world—empowering people by providing tools to run businesses in places and situations not usually served by traditional financial institutions.

In this context, it’s clear from talking to Berger that he is very focused on metrics, reporting, and visibility.

“We track everything via Salesforce,” he told us. “We track activities and results on a daily, weekly, and monthly basis. We look at profit and adjusted revenue targets quarterly. We start with a large number and distill the number downwards to figure out goals for each member of the team.”

Even so, when we asked him what his biggest focus was, his answer surprised us.

For Andrew, motivating sales teams doesn’t start with hitting the numbers or driving people to get better results.

It starts with communication—with motivating everyone on his team to buy into the greater mission Square has as a company: economic empowerment.

“My biggest piece of the motivational side is tying the work we do as individuals to the mission we have as a company,” he told us.


How to motivate a sales team: Andrew with members of the Square Sales team. Andrew with members of the Square Sales team.


“When I first started, our mission was to make commerce easy for small business owners who wanted to sell their goods and services. And we revolutionized how that process works for millions of people.”

“When the mission changed to economic empowerment, we had to change the way we thought about our work,” he continued.

“Today, what we do in sales, whether it’s prospecting, closing or whether we’re onboarding a new customer, these are the activities that fund what Square is doing around the world—empowering people who would not otherwise be able to start or run a business.”

Note: Troops can help your Sales team automate tasks, be more productive, and close more deals. Sign up for a free trial.

Kathryn Stephan

Written by Kathryn Stephan

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