Head of Mid-Market Sales

Block; San Francisco (CA); On-site; USD 319,000 - 479,000; Full time

Benefits offered by this job

Remote work

Medical insurance

Flexible time off

Retirement savings plans

Job summary

Block is seeking a dynamic Head of North American Mid-Market Sales to lead and scale revenue across Cash App and Afterpay. You will coach senior Account Executives, drive complex negotiations, and align cross-functional teams to win strategic deals with mid-market brands across North America.

The role emphasizes strategic leadership, customer value, and a high-performance culture within a fast-growing payments environment.

Qualifications

• 12+ years in high-growth environments leading Mid-Market Sales or Account Management.
• Experience with large-scale established clients and matrixed organizations.
• Proven ability to lead teams, drive revenue growth and exceed targets.

Responsibilities

• Oversee NA Mid-Market Sales Team and coach Account Executives.
• Develop cross-functional partnerships with Marketing, Finance, Product, Risk, Legal.
• Craft deal strategy and pitch value propositions to senior decision makers.
• Drive portfolio strategy and communicate market insights to align GTM.

Skills

Mid-Market Sales

Team Leadership

Negotiation

Cross-functional Collaboration

Stakeholder Management

Strategic Thinking

Data Analytics

Job description

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 toforge 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 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

Pay Transparency:

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.

All Zones: ($319,000 - $478,600)

Application Guidelines

Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.

Use of AI in Our Hiring Process

We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws.

Contact us herewith hiring practice or data usage questions.

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering.

Check out our other benefits at Block.

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people.Squaremakes commerce and financial services accessible to sellers.Cash Appis the easy way to spend, send, and store money.Afterpayis transforming the way customers manage their spending over time.TIDALis a music platform that empowers artists to thrive as entrepreneurs.Bitkeyis a simple self-custody wallet built for bitcoin.Protois a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.