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Mid-Market Account Executive, Commerce

Block· 20229 S&M - Sales - Commerce Enterprise and Mid
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Chicago, IL$217.8k - $326.8kfull-timePosted 1mo ago

About the role

Mid-Market Account Executive responsible for building and expanding relationships with high-potential North American merchants, driving revenue for Cash App Pay and Afterpay across commerce payments products. Owns a portfolio from prospecting through contract and launch, collaborates cross-functionally, and travels as needed.

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.

Qualifications

  • 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.

Skills

Required:Full-cycle B2B salesPipeline developmentNegotiationCross-functional collaboration

Benefits

  • Remote work
  • medical insurance
  • flexible time off
  • retirement savings plans
  • modern family planning
  • employee benefits (see company pages)
Last updated Sep 16, 2026. Interested? Apply on the company site.
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About Block

Block builds technology to increase access to the global economy.

Made up of Square, Cash App, Afterpay, TIDAL, Bitkey, and Proto, Block, Inc. builds technology to increase access to the global economy.

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