← All roles

Senior Account Executive, Mid-Market

Block· 20213 S&M - Sales - Square Outside
Apply on company site
Hybrid (Toronto, Ontario)CA$193.4k - CA$290.2kfull-timePosted 3w ago

About the role

Senior Sales Account Executive on the Mid-Market Team responsible for driving multi-product deals from outbound prospecting to close, building and managing a high-quality pipeline, and delivering revenue targets across Square’s ecosystem for mid-market merchants.

Responsibilities

  • 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.

Qualifications

  • 5+ years of full-cycle B2B sales experience with consistent quota achievement.
  • Proven success in outbound prospecting and net-new business creation (SaaS or fintech preferred).
  • Experience closing complex, multi-threaded deals with longer sales cycles.
  • Ability to build pipeline from scratch using targeted, strategic outreach.
  • Exceptional communication, presentation, and negotiation skills across phone, video, and written channels.
  • Strong consultative selling skills — diagnose business challenges and map tailored solutions.
  • A hunter’s mindset — resilient, creative, and driven to win.
  • Ability to work independently while contributing to a team-first environment.
  • Advanced proficiency with Salesforce and modern sales tools.
  • BA/BS degree or equivalent experience

Skills

Required:Full-cycle B2B salesOutbound prospectingMulti-product solution sellingSalesforce

Benefits

  • Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering.
Last updated Sep 30, 2026. Interested? Apply on the company site.
Block logo

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.

technologyfinancial servicesdigital paymentsmusic streaming
Company profileWebsite

More open roles at Block