The Complete Square Account Executive Review Guide

8 months ago   •   4 min read

By Bravado Staff

Learn about the Square Account Executive salary, culture, and interview process.

Role Basics

What type of work experience do you need for this role?

For an SMB Account Executive position, you are required to have 1-2 years full cycle sales experience. Alternatively, you do not need closing experience if you come from their BDR program.

A Mid-Market Account Executive will be required to have 3-9 years of full cycle sales experience.

An Enterprise Account Executive will be required to have at least 9 years of full cycle sales experience.

How is the sales org structured?

Square structures their Sales Org by account size: SMB, Mid-Market, and Enterprise.

Square has ADR’s and BDR’s that support the Account Executives as well. As an SMB Account Executive, you will share a BDR with a 2-3 other Account Executives. At the Enterprise level, you will have a dedicated BDR.

What does an Account Executive do at Square?

Square Account Executives are responsible for full cycle sales. At the SMB level, you do not travel, whereas at the Mid-Market or Enterprise level you might spend more time on traveling to your bigger clients.

Which Square offices do Account Executives work at?

Square salespeople are scattered throughout all of their offices. The main offices are New York and San Francisco, but you will also find salespeople in the St. Louis, Atlanta, and Scottsdale offices.

Does Square have a leveling system for sales?

Yes. Each account size segmentation (SMB, Mid-market, and Enterprise) have level 1 and level 2 reps.

For example, the levels are:

  • SMB AE 1, SMB AE 2
  • Mid Market AE 1, Mid Market AE 2
  • Enterprise AE 1, Enterprise AE 2

Interview Process

What's the intervew process like?

A typical interview process will look like this:

  1. Submit Application
  2. Complete HireVue self-recorded video interview
  3. Call with Recruiter/HR
  4. Call with Hiring Manager
  5. Panel Interview with three to five people – AE’s, hiring manager, 1-2 other sales managers

Expect the process to take 2-4 weeks.

What are the interview questions?

  • Walk me through your resume
  • Describe your sales process
  • Describe your previous role and experience in sales
  • What are your strengths and weaknesses
  • Why do you want to work at Square
  • How did you prepare for this interview
  • What products does Square sell
  • How can Square’s products help a business
  • What is the Square value-add
  • Who are Square’s competitors
  • What type of deals does Square typically win and what type do they lose?
  • Mock Call with the Panel – You will be roleplaying as a Square AE and your goal will be to try to close them.

How do I prepare for the interview?

  • The best way to get an interview is through an internal referral
  • Know the Square products well
  • Know your sales experience and past deals well
  • Be prepared to answer how you prepared for the interview
  • Read up on Square’s products and culture on their website

Sales Culture

What's the Square sales culture like?

Square has a relatively laid-back sales environment. It is rare for salespeople to get fired for bad performance at Square. Square gives stock that takes 4 years to fully vest, so people tend to stick around for multiple years. Overall, most salespeople seem to be happy with their job at Square.

How many hours per week do Square account executives work?

Account Executives will work 40 to 45 hours per week on average. If you’re ahead of your quota, you’ll work less, if you’re not hitting quota, you’ll work more.

What's the day-to-day of a Square Account Executive like?

As an Account Executive, your days are split between doing inbound or outbound. Half your day you might be working on a deal from an inbound lead, and then other half of the day you might be working on an outbound deal or outbound prospecting (e-mails, calls, researching materials for your BDR to send out). Like most sales jobs, the remainder of your day will be spent with administrative work like updating Salesforce.

Salary, Commission, and Quota

How much does a Square Account Executive make?

For detailed compensation data, visit our Square company page.

All salespeople have access to the employee stock purchase program (ESPP).

How are the quotas structured?

SMB and Mid-Market Account Executives have a quarterly quota. Enterprise Account Executives have a half-year quota.


How competitive is the product and solution set?

Square is one of the top players in the market. It has a strong brand name, with success stories at the SMB to Enterprise level. In the payment processing vertical, it is hard to beat selling for Square.

Who does Square compete with?

Toast, Clover, and Shopify are the big competitors.

Tips to Succeed

What is the best Square sales org to sell in?

The best sales org is the enterprise org. As an Enterprise account executive, you get paid the most money, work with the largest accounts, and do the largest deals. Because of the smaller number of accounts, this leads to a better work life balance and less time spent grinding out prospecting.

The caveat is that to become an enterprise account executive, you need several years experience selling in the enterprise space, so it is quite competitive to get into this role.

How big of a role does territory play in your success?

At the SMB level, Square does not have territories. You can go after any account you want within the US.

What advice would you give to a new rep?

  • As an SMB rep, prepare to do a heavy amount of outbound prospecting.
  • Find a top performing rep to mentor you and learn as much as possible from them.
  • Prepare to invest a lot of time into learning the products. Square sells payroll, loyalty, marketing, credit card processing, point of sales, and more. There are hundreds of integrations and extensions to each of those product lines. The top reps know the products inside and out.
  • Quotas are tough to hit so you should be prepared to not hit your quota multiple quarters per year. The quotas are set very high at Square and there are quarters where nobody in the office will hit their quota and next quarter management won’t adjust it (SMB). Despite this, most people are pretty happy and don’t leave due to the benefits, culture, and higher base pay.

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