Description
The North American Mid-Market Sales team at Cash App and Afterpay is responsible for driving revenue across commerce payments products. As a Mid-Market Account Executive, you will 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.
Responsibilities:
- 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.
Requirements:
- 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 meetings, industry events, and internal team moments.