Head of Mid-Market Sales

The North American Mid-Market 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 Mid-Market Sales to forge and expand relationships with fast-growing and established 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 executive leadership and senior stakeholders at high-growth and established mid-market companies. You will be responsible for sophisticated deal negotiation and execution with leaders in commerce while winning business at scale 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, effective influencer, and skilled at balancing high-touch relationship building with a scalable, process-driven sales motion. Beyond ultimately being responsible for revenue outcomes across our Mid-Market merchant pipeline – which comprises high-growth and established consumer brands in North America across retail, fashion, beauty, travel, QSR, home 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 at scale, leading and managing high performing teams and a dedication to continuous improvement. You will: • Oversee the North American Mid-Market Sales Team: Lead a team of seasoned Mid-Market Account Executives. Coach the team to navigate sophisticated deal negotiations while winning business at scale. 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 and Afterpay. • 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. You can influence without authority across teams and build the internal relationships required to navigate a distributed and matrixed set of stakeholders. • Build an A-Team: You will inherit a team of strong performers with relevant experience. Further develop their skills, knowledge, efficacy and an overall team culture focused on performance and betterment. • Be the Voice of Cash App and Afterpay: Represent the business to leading Mid-Market 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 leadership teams. • 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 high-growth and established brands across North America. 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 Mid-Market 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 Mid-Market Sales, or Mid-Market Account Management organizations, preferably in a fast-moving technology or financial services company and experience working with large-scale established clients • Proven experience navigating and operating effectively within matrixed global organizations • A demonstrated track record of leading teams that consistently drive revenue growth and exceed 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 you 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 judgment internally and externally at large companies, including at the C-suite level • An operational mindset as well as a strategic one - you can implement robust processes and lead teams through complex relatio