Mid-Market Account Executive, Commerce

This is a fully remote position, open to applicants in Illinois.

📋 Description

• Manage a portfolio of mid-market opportunities, overseeing everything from prospecting and qualification to discovery, negotiation, contracting, launch, and final handoff.

• Create account plans that identify merchant priorities, key decision-makers, potential blockers, and revenue opportunities.

• Generate a pipeline through outbound outreach, market research, lead assignments, vertical insights, events, referrals, and introductions from partners.

• Assess and prioritize opportunities based on compatibility, revenue potential, product alignment, implementation requirements, and probability of closing.

• Conduct discovery sessions with both business and technical stakeholders.

• Develop merchant-specific business cases and sales narratives for Cash App Pay and Afterpay.

• Create commercial proposals and negotiate pricing, financial terms, contracts, procurement needs, and implementation dependencies.

• Organize deal teams across Product, Engineering, Marketing, Finance, Legal, Risk, Sales Strategy, and Operations.

• Oversee deal milestones, next steps, stakeholder responsibilities, and internal approvals.

• Keep opportunity data, pipeline reports, and sales forecasts updated in Salesforce and related systems.

• Provide merchant feedback, competitive intelligence, and market insights to Product and go-to-market teams.

• Contribute to sales processes, enablement materials, and operational rhythms.

• Achieve 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 similar go-to-market role.

• Preferably experienced in commerce, payments, fintech, SaaS, retail technology, or another fast-paced technology environment.

• Proven track record of meeting or exceeding quotas and closing mid-market or complex commercial deals.

• Strong skills in prospecting and generating a pipeline.

• Possess executive presence and the capability to influence senior stakeholders.

• Strong commercial judgment and negotiation abilities.

• Proficient in using data to build business cases, prioritize opportunities, assess pipeline quality, and communicate trade-offs.

• Demonstrated product curiosity and technical fluency in payments, commerce, customer acquisition, marketing, and merchant growth.

• Self-starter with a comfort level in ambiguity, change, and shifting priorities.

• Skills in cross-functional collaboration and the ability to lead workstreams without formal authority.

• Exceptional written and verbal communication skills.

• A mindset focused on continuous improvement.

• Willingness to travel for merchant meetings, industry events, and internal team engagements.

🏝️ Benefits

• Remote work options.

• Medical insurance coverage.

• Flexible time off policies.

• Retirement savings plans.

• Modern family planning benefits.

• Inclusive interview experience with reasonable accommodations.

• Commitment to equal opportunity employment.