Mid-Market Account Executive, Remote

Block, Inc

• $156K — $234K *
Business Services
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • 4+ years of sales experience in a full cycle closing role
  • BA/BS degree or equivalent experience
  • Proven track record of exceeding sales targets and handling complex deals
  • Experience in business development and new logo acquisition
  • Ability to operate independently in a fast-paced environment
  • Collaborative mindset and team player
  • Prior experience with Salesforce or similar CRM tools

Responsibilities

  • Own the complete outbound sales cycle from prospecting to close for mid-market merchants
  • Build and manage a high-quality sales pipeline through various outreach methods
  • Develop and tailor multi-product solutions to meet unique merchant needs
  • Collaborate with Business Development on lead flow while pursuing net-new logo acquisition independently
  • Conduct impactful discovery, demos, and negotiations across multi-stakeholder deals
  • Act as a trusted advisor, flexibly handling roles as needed
  • Work cross-functionally with Product, Marketing, and Operations to create cohesive solutions
  • Maintain disciplined management of pipeline and ensure accuracy in Salesforce forecasting
  • Consistently achieve and exceed monthly and quarterly revenue goals

Benefits

  • Remote work flexibility
  • Medical insurance
  • Flexible time off
  • Retirement savings plans
  • Modern family planning support
Full Job Description
The Role

At Square, we're re-imagining how mid-market businesses grow. As a Senior Sales Account Executive on our Outbound Team, you'll bring Square's ecosystem to new sellers across diverse industries by building, shaping, and closing your own pipeline. You'll run sophisticated, multi-product deals from the first touch to final close - blending hunter instincts, consultative depth, and strategic execution.

If you're an experienced closer who thrives in outbound environments, loves solving meaningful business challenges, and consistently delivers against ambitious targets - this is your role.

You Will
  • Own the full outbound sales cycle - from prospecting to negotiation to close - with mid-market merchants.
  • Build and manage a high-quality pipeline through cold outreach, social selling, targeted campaigns, and creative outbound strategies.
  • Develop multi-product solutions across Square's ecosystem and tailor them to each merchant's unique needs.
  • Partner with Business Development on lead flow while independently driving net-new logo acquisition.
  • Conduct high-impact discovery, demos, and negotiations with decisiveness across multi-stakeholder deals.
  • Act as a consultant and trusted advisor - seamlessly flexing across BDR, AE, and AM responsibilities when needed.
  • Collaborate cross-functionally with Product, Marketing, Implementation, and Operations to deliver cohesive solutions.
  • Maintain disciplined pipeline management and forecasting accuracy in Salesforce.
  • Consistently hit and exceed revenue goals - monthly and quarterly.

You Have
  • 4+ years of sales experience in a full cycle closing role
  • A BA/BS degree or relevant experience
  • Demonstrated exceeding sales targets, selling a diverse ecosystem of products, and closing complex deals
  • The ability to drive deals independently in a fast-paced, dynamic environment
  • Business development experience (e.g. new logo sourcing and acquisition)
  • A collaborative and team player mentality
  • Prior Salesforce experience or equivalent

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.

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