Mid-Market Strategic Sales Lead

  • San Francisco, CA, United States
  • Employees can work remotely
  • Full-time

Company Description

oin a movement in which everyone can win. We started a movement in which everyone can win – shoppers, retailers, society and every person on our team. To play fair, trust people and reward them for doing the right thing. We see and feel the impact of our work as more and more people gain financial freedom and retailers grow across the globe.

Founded seven years ago in Sydney, Australia, Afterpay has millions of active customers globally and is offered at the world’s best retailers around the world including Anthropologie, Revolve, DSW, GOAT, Finish Line, Levi’s, Mac Cosmetics, Ray-Ban and many others. Afterpay is on a mission to power an economy in which everyone wins.

Afterpay is completely free for customers who pay on time – helping people spend responsibly without incurring interest, fees or extended debt. Afterpay empowers customers to access the things they want and need, while still allowing them to maintain financial wellness and control, by splitting payments in four, for both online and in-store purchases. Afterpay is deeply committed to delivering positive outcomes for customers. We are focused on supporting our community of shoppers.

We trust in the next generation and share a vision of a more accessible and sustainable world in which people are rewarded for doing the right thing.

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 Sales Lead 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 responsible for driving strategy & execution of complex deals across a team of incredible Sales team members with leading brands in commerce, in addition to supporting strategic projects, programs and outcomes across the Enterprise organization.  

This role requires a strategic problem solver who is an effective influencer with a high degree of business acumen. They thrive in challenging, fast-paced environments and have a passion for driving creative solutions and developing others. The ideal candidate has demonstrated excellence in delivering or exceeding demanding targets and shaping scalable organizations. Leadership, change management, data driven decision making, and a dedication to continuous improvement are also key skills for the role.

You Will:

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

  • Coach Deals: Lead a team of Sales representatives to navigate complex and often first-of-kind deal negotiation and execution for the Block organization by designing playbooks for methodical deal management, holding team members to business OKRs, and clearing internal & external blockers to revenue generation.

  • Drive Portfolio Strategy: Leverage insights across your team’s deal experience to centralize & socialize the very best sales narratives that resonate with Mid-Market merchants. Feed key insights back to the broader Enterprise leadership team to inform deal strategy across Merchants of all sizes to position Block to win deals. Develop strategies aligned with revenue plans, portfolio OKRs and product roadmaps.

  • Build an A-Team: Recruit, hire and develop a team of top-performing Sales representatives. Partner closely with cross-functional teams to better support your team in driving 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.


  • 10+ years experience in high-growth environments in a business development, sales, GTM or strategy role, preferably in a fast-moving technology or financial services company 

  • Excellent leadership skills with the ability to develop talent, build strong cross-functional relationships and work collaboratively

  • 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 

  • 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 

  • Comfortable working with analytics & tools that support business performance measurement & management 

  • 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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