Head of Enterprise Sales, North America Bay Area, CA, US

It all started with an idea at Block in 2013. Initially built to take the pain out of peer‑to‑peer payments, Cash App has gone from a simple product with a single purpose to a dynamic ecosystem, developing unique financial products, including Afterpay/Clearpay, to provide a better way to send, spend, invest, borrow and save to our 50+ million monthly active customers. We want to redefine the world’s relationship with money to make it more relatable, instantly available, and universally accessible. Today, Cash App has thousands of employees working globally across office and remote locations, with a culture geared toward innovation, collaboration and impact. We’ve been a distributed team since day one, and many of our roles can be done remotely from the countries where Cash App operates. No matter the location, we tailor our experience to ensure our employees are creative, productive, and happy.

The Role

The North American Enterprise Sales team at Cash App is responsible for driving revenue to our core consumer payments businesses at Cash App and Afterpay, giving our Merchant partners access to the largest and most engaged network of next generation consumers.

We are looking for a high‑energy, dynamic, and thoughtful Head of Enterprise Sales to forge and expand relationships with the largest global brands and unlock new revenue opportunities across our portfolio of Pay Now and Pay Later 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 Cash App and Afterpay. You will have a demonstrated ability to navigate ambiguity; think strategically and operationally about business, marketing and technical challenges; and lead cross‑functional workstreams to launch product and commercial initiatives. This role requires a strategic problem solver who is a relentless negotiator and effective influencer.

Beyond ultimately being responsible for revenue outcomes across our enterprise merchant pipeline – which comprises some of the most well‑known consumer brands in the world across retail, fashion, travel, big box, QSR, digital gaming and more – you will be responsible for building and supporting a strong culture of performance. You excel at developing others and leading with empathy but without ego.

The ideal candidate has demonstrated excellence in complex commercial negotiations, leading and managing high‑performing teams and a dedication to continuous improvement.

You Will

• Oversee the North American Enterprise Sales Team: Lead a team of seasoned Enterprise Account Executives. Coach the team to navigate complex and often first‑of‑kind new business opportunities. Support deal negotiations through internal and external advocacy, particularly by clearing blockers to revenue. Craft a segment‑wide strategy and hold the team accountable to delivering on OKRs and executing against revenue targets, in concert with the broader Sales & Account Management function at Cash App.
• Develop Meaningful Cross‑Functional Partnerships: Work closely with cross‑functional teams to better support your team in generating revenue, including Marketing, Finance, Product, Risk, Legal, Account Management and more. Influence without authority across teams and build the internal relationships required to navigate a globally distributed and matrixed set of stakeholders.
• Build an A‑Team: Inherit a team of strong performers with relevant experience. Further develop their skills, efficacy and overall team culture focused on performance and betterment.
• Be the Voice of Cash App and Afterpay: Represent the business to top‑tier Enterprise Merchants as a thought‑leader in the payments landscape and demonstrate Cash App and Afterpay’s value as a growth driver for our commerce partners. Develop and grow Block’s relationships with merchant partners, including their senior executives.
• Craft Deal Strategy: Develop and pitch powerful sales narratives that educate prospective merchants of Cash App and Afterpay’s value proposition. Effectively communicate with senior decision makers at the largest brands in the world. Leverage insights, data and market intel to continuously improve our go‑to‑market strategy.
• Drive Portfolio Strategy: Leverage insights across your team’s portfolio to centralize & socialize the very best sales and growth narratives that resonate with Enterprise Merchants and inform our B2B marketing and sales strategy.
• Be the Voice of the Merchant: Represent market feedback and sentiment internally, advocating for your clients while balancing against the needs and constraints of our business, by aggregating and delivering key insights across the organization in a structured, consistent, and proactive manner.

You Have

• An obsession with our products and a motivation fueled by feeling the impact of your work as more consumers build financial wellness with Cash App & Afterpay.
• 12+ years experience in high‑growth environments leading Product Partnerships, Enterprise Sales, or Enterprise Account Management organizations, preferably in a fast‑moving technology or financial services company and experience working with large‑scale Enterprise clients.
• Proven experience navigating and operating effectively within matrixed global organizations.
• A demonstrated track record of leading teams that consistently drive revenue growth and meet their revenue targets.
• Excellent leadership skills with the ability to develop talent, motivate high‑performing teams and build strong cross‑functional relationships. You put your people in the best position to succeed and your management style is tailored to each individual to maximize their performance and engagement at work.
• A high familiarity and comfort with how product development works, preferably in payments. You hold your own interfacing with stakeholders across disciplines (technical, marketing, product) and have credibility with your internal product and engineering colleagues.
• Strong executive presence, with demonstrated ability to influence and earn trust with senior leaders, ask the right questions, and use sound business judgement internally and externally at large companies, including during C‑suite level interactions.
• An operational mindset as well as a strategic one – you can implement robust processes and lead teams through complex relationships as well as set a clear vision.
• Comfort working with analytics & tools that support business performance measurement & management.
• Creative storytelling abilities, able to seek out relevant, meaningful data and build business cases to inform partners on Cash App and Afterpay’s value proposition.
• A scrappy and humble mindset, where toggling between team lead and in‑the‑weeds work is business as usual. You’re equally comfortable writing an annual plan as you are rolling up your sleeves to support one of your team members. You get the job done and inspire others to do so as well.
• A willingness to travel.

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

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. Areas not listed can be discussed with a recruiter.

Zones A – D: $319,000 – $478,600 (Amounts listed above include target variable compensation).

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