Mid-Market Strategic Sales, North America

  • 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.

To solve this problem, we expanded into software and built integrated solutions to help sellers sell online, manage inventory, 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

The North American Enterprise team at Block is responsible for driving revenue to Block’s core businesses (Afterpay, Cash App, Square) through commerce, giving our Merchant partners access to the largest and most engaged network of next generation consumers. 

We are looking for a high-energy, dynamic strategic thinker to forge and expand Block’s relationships with the largest global brands and unlock new revenue opportunities across our expanding portfolio of payments products. You will be on the front lines of a fast-growing payments business - partnering with business owners and leading executives of Fortune 500 companies. You will be responsible for complex and first-of-kind deal negotiation and execution with leaders in commerce. 

A successful candidate thrives in a challenging, fast-paced environment, has a passion for developing and expanding client relationships, and exhibits a strong sense of ownership to win new business for Block. You will have a demonstrated ability to navigate ambiguity, think strategically and operationally about business, marketing and technical challenges; and lead cross-functional teams to launch product and commercial initiatives.

You will:

  • Be the Voice of Block: Represent Block to top-tier Enterprise & Mid-Market Merchants as a thought-leader in the payments landscape and demonstrate Block’s value as a growth driver for our commerce partners 

  • Quarterback Deals: Be responsible for complex and often first-of-kind deal negotiation and execution for the Block organization through methodical deal management based on milestone tracking, KPIs, and partner alignment on opportunities of mutual interest

  • Craft Deal Strategy: Develop and pitch powerful sales narratives that educate prospective partners of Block’s value proposition. Effectively communicate with senior decision makers at the largest brands in the world.

  • Be a Team Player: Partner closely with cross-functional teams to drive deals forward, including Marketing, Finance, Product, Risk, Legal, Operations, Customer Service; and with external partners’ cross-functional executives

  • Build Block’s Network: Develop and grow Block’s relationships with leading brands, including their senior executives. Represent Block at industry events, trade shows and networking functions.


  • 6+ years experience in high-growth environments in a business development, sales, GTM or strategy role, with at least 2 years in a MID/ENT role preferably in a fast-moving technology or financial services company

  • Strong executive presence, with demonstrated ability to influence and earn trust with senior leaders, ask the right questions, and use sound business judgment internally and externally at large companies, including at the C-suite level 

  • A self-starter mentality, where leaning in and wearing multiple hats in a fast-paced, often ambiguous environment is business-as-usual 

  • A hunger to problem solve with analytical rigor. You’re a killer sales person and strategic thinker who comes armed to internal and external conversations with the right data and analysis to make a convincing argument.

  • An operational mindset, with an ability to lead teams through complex deal constructs, relationships and organizations by setting a clear vision and implementing robust processes 

  • Significant experience driving and executing on complex deal work and strategy

  • Creative storytelling abilities, able to seek out relevant, meaningful data and build business cases to inform partners on Block’s value proposition

  • A willingness to travel

Additional Information

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, 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, and always assess candidates on an individualized basis.


We want you to be well and thrive. Our global benefits package includes:

  • Healthcare coverage
  • Retirement Plans
  • Employee Stock Purchase Program
  • Wellness perks
  • Paid parental leave
  • Paid time off
  • Learning and Development resources

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.

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