Head of Field Sales

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, 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. .

The Role

Square is looking for a Head of Field Sales 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. You will help build a vision and strategy plan for winning market share in each of the territories. 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. 

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

• 10+ years of sales success, preferably in a high growth company
• 6+ years of leadership experience, experience leading a team of field account executives
• 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
• Experience scaling and overseeing a large Field Sales team

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 an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We also consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis.

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.

Block will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances.

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.

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. 

Zone A:
$304,500—$456,700 USD
Zone B:
$304,500—$456,700 USD
Zone C:
$304,500—$456,700 USD
Zone D:
$304,500—$456,700 USD