Senior Sales Manager, Field Sales

  • Full-time

Company Description

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality through Afterpay, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

Job Description

Square is looking for a senior sales leader to lead our newly established field sales organization.  Our goal is to bring a local experience to our Sellers (aka customers/merchants) everywhere.  You will engage with our Territory AEs and Sellers in a relevant and authentic way, demonstrate Square’s mission of economic empowerment and provide a local presence.  

You will be responsible for planning, organizing, and leading our field sales teams focused on selling to SMB merchants (less than $50M in revenue) restaurants, retailers and service based businesses in our largest and highest potential markets. This role is a frontline and strategic leadership role where you’ll be managing a team of 5-7 quota carrying high velocity Territory Account Executives. You will help build a vision and strategy plan for winning market share in your assigned cities.  You will collaborate with cross functional partners to build top of funnel leads, referrals, connect with local partners, attend/host local events within your community to generate new business, kickstarting the flywheel and build Square’s brand awareness within designated cities. 

Your leadership will directly help Square drive revenue against our annual sales quotas. Your entrepreneurship spirit will be a valuable contribution to developing Square’s sales strategy, increasing the size and impact of the team and establishing a culture of crisp execution. This role reports to the Head of North America SMB+ Sales.  This is a great opportunity to participate in our new phase of growth.  Travel minimum of 50% to co-sell with the sales team. 

You will:

  • Be obsessed with exceeding quota, execution, ownership and operational excellence

  • Build a high performance sales culture that embraces individual/team development, co-selling, coaching, recognition, and accountability

  • Build and execute a business plan with your team that outlines how to capture and retain market share in your assigned cities 

  • Data driven mindset - seeks to understand and makes decisions and suggestions through consistent review of KPIs  (SaaS, win rates, activations, activities) and identify market growth indicators (drop-ins, in-person sales motion, resources)

  • Be responsible for ramping your team, leading your team to reach KPIs and revenue targets and traveling to perform in-person selling alongside your team.  

  • Demonstrate exceptional judgment, critical thinking skills and engender trust with your team, peer leadership, senior management and cross functional partners

  • Ability to embrace and communicate change management along with an ability inspire and motivate team members


You have:

  • 6+ years of sales success, preferably in a high growth company

  • 4+ years of leadership experience, experience leading a team of field account executives (preferred)

  • Experience in high transaction volume SaaS application or financial services sales 

  • Proven track record of creating a winning culture that performs at a high level

  • Extensive experience in a metrics-driven sales organization

  • Proven ability to work with and influence cross-functional teams and departments in a rapidly growing environment

  • Proven ability to communicate and manage relationships with senior executives

  • Excellent interpersonal, leadership, organizational, and communication skills

  • BA/BS Degree 

Additional Information

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

Zone A: USD $239,600 - USD $359,400
Zone B: USD $222,800 - USD $334,200
Zone C: USD $210,900 - USD $316,300
Zone D: USD $203,700 - USD $305,500

To find a location’s zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information. 

Full-time employee benefits include the following:

  • Healthcare coverage (Medical, Vision and Dental insurance)
  • Health Savings Account and Flexible Spending Account
  • Retirement Plans including company match 
  • Employee Stock Purchase Program
  • Wellness programs, including access to mental health, 1:1 financial planners, and a monthly wellness allowance 
  • Paid parental and caregiving leave
  • Paid time off (including 12 paid holidays)
  • Paid sick leave (1 hour per 26 hours worked (max 80 hours per calendar year to the extent legally permissible) for non-exempt employees and covered by our Flexible Time Off policy for exempt employees) 
  • Learning and Development resources
  • Paid Life insurance, AD&D, and disability benefits 

These benefits are further detailed in Block's policies. This role is also eligible to participate in Block's equity plan subject to the terms of the applicable plans and policies, and may be eligible for a sign-on bonus. Sales roles may be eligible to participate in a commission plan subject to the terms of the applicable plans and policies. Pay and benefits are subject to change at any time, consistent with the terms of any applicable compensation or benefit plans.

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. 

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we’re doing to build a workplace that is fair and square? Check out our I+D page.

Additionally, we consider qualified applicants with criminal histories for employment on our team, assessing candidates in a manner consistent with the requirements of the San Francisco Fair Chance Ordinance.


We’ve noticed a rise in recruiting impersonations across the industry, where individuals are sending fake job offer emails. Contact from any of our recruiters or employees will always come from an email address ending with,,, or,

Block, Inc. (NYSE: SQ) is a global technology company with a focus on financial services. Made up of Square, Cash App, Spiral, TIDAL, and TBD, we build tools to help more people access the economy. Square helps sellers run and grow their businesses with its integrated ecosystem of commerce solutions, business software, and banking services. With Cash App, anyone can easily send, spend, or invest their money in stocks or Bitcoin. Spiral (formerly Square Crypto) builds and funds free, open-source Bitcoin projects. Artists use TIDAL to help them succeed as entrepreneurs and connect more deeply with fans. TBD is building an open developer platform to make it easier to access Bitcoin and other blockchain technologies without having to go through an institution.

While there is no specific deadline to apply for this role, on average, U.S. open roles are posted for 70 days before being filled by a successful candidate.

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