Mid-Market Account Executive, Commerce Remote Chicago, IL, US
Afterpay
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- SEE ALL JOBS; Mid-Market Account Executive, Commerce Apply Remote Chicago, IL, US Req ID: R0005559 Posted Date: 09/15/26 Posted yesterday Apply Job DetailsApply 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 Mid-Market Sales team at Cash App and Afterpay is responsible for driving revenue across our commerce payments products, giving merchant partners access to one of the largest and most engaged networks of next-generation consumers. We partner with high-growth and established brands across retail, fashion, beauty, travel, QSR, home, health and wellness, ticketing, and other commerce categories to help them acquire customers, increase conversion, and grow profitably.
- We are looking for an experienced Mid-Market Account Executive to build and expand relationships with high-potential merchants across North America. You will own a portfolio of prospective merchants, create new pipeline, lead a consultative sales process, and close new business across Cash App Pay and Afterpay.
- You will work with founders, executives, and leaders across commerce, marketing, payments, finance, and technology. Internally, you will coordinate partners across Product, Engineering, Marketing, Finance, Legal, Risk, Sales Strategy, and Operations.
- In this role, you will independently own complex sales workstreams, make informed tradeoffs, and influence deal strategy and execution within your area of responsibility. Success requires balancing high-touch relationship development with a structured and repeatable sales process.
- You will:
- Own a portfolio of mid-market opportunities from initial prospecting and qualification through discovery, negotiation, contracting, launch, and handoff.
- Develop account plans that identify merchant priorities, key decision-makers, potential blockers, and revenue opportunities.
- Build pipeline through outbound outreach, market research, internal lead assignments, vertical insights, events, referrals, and partner introductions.
- Qualify and prioritize opportunities based on merchant fit, revenue potential, product alignment, implementation requirements, and likelihood to close.
- Lead discovery with business and technical stakeholders to understand merchant priorities, customer needs, payment flows, and implementation requirements.
- Build merchant-specific business cases and sales narratives that connect Cash App Pay and Afterpay’s capabilities to customer acquisition, conversion, and growth goals.
- Develop commercial proposals and negotiate pricing, financial terms, contracts, procurement requirements, and implementation dependencies.
- Coordinate deal teams across Product, Engineering, Marketing, Finance, Legal, Risk, Sales Strategy, and Operations.
- Manage deal progress using defined milestones, next steps, stakeholder ownership, and internal approval requirements.
- Maintain accurate opportunity data, pipeline reporting, and sales forecasts in Salesforce and related systems.
- Bring merchant feedback, competitive intelligence, and market insights back to Product and go-to-market teams.
- Contribute to sales processes, enablement materials, and operating rhythms that improve pipeline quality, deal velocity, forecast accuracy, and win rates.
- Deliver against individual revenue and sales targets.
- Represent Cash App and Afterpay in merchant meetings, industry events, and networking forums.
You have:
- 5+ years of experience in full-cycle B2B sales, business development, partnerships, or a related go-to-market role, preferably in commerce, payments, fintech, SaaS, retail technology, or another fast-moving technology environment.
- A demonstrated track record of meeting or exceeding quota and closing mid-market or complex commercial deals.
- Strong prospecting and pipeline-generation skills, including comfort building new business through outbound outreach, market research, partner referrals, events, and executive networking.
- Executive presence with the ability to earn trust, ask strong questions, influence senior stakeholders, and tailor communication to founders, functional leaders, and cross-functional buying committees.
- Strong commercial judgment and negotiation skills, including comfort working through pricing, legal terms, procurement, implementation dependencies, and internal approval processes.
- Comfort using data to build a business case, prioritize opportunities, inspect pipeline quality, and communicate tradeoffs.
- Product curiosity and technical fluency, especially around payments, commerce, customer acquisition, marketing, and merchant growth.
- A self-starter mentality and comfort operating through ambiguity, frequent change, and evolving priorities while still delivering results.
- Excellent cross-functional collaboration skills and the ability to lead workstreams without formal authority.
- Strong written and verbal communication skills, including the ability to build concise, compelling narratives for internal and external audiences.
- A continuous-improvement mindset and willingness to help build better team processes, enablement materials, and operating rhythms.
- A willingness to travel for merchant m