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Field Sales Director, Central Region

Block· 20249 S&M - Sales - Square Field Sales
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Chicago, IL$318k - $477kfull-timePosted 1w ago

About the role

Square is seeking a Field Sales Director to scale and lead the Central Region field sales organization, building a high-performing team of Sales Managers and Territory Account Executives, driving strategy, execution, and growth across key Central markets while promoting Square’s ecosystem and omnichannel solutions.

Responsibilities

  • Scale with purpose: Strengthen and expand the Central Field Sales organization by refining territory models, optimizing go-to-market plans, and instilling operational rigor.
  • Drive to win: Build a culture grounded in performance, accountability, and competitiveness—where teams are motivated to exceed targets and celebrate excellence.
  • Lead from the front: Spend meaningful time in the field—co-selling, coaching, and demonstrating product fluency through action.
  • Be a product expert: Master Square's ecosystem end-to-end and ensure your teams sell consultatively—connecting product capabilities to seller outcomes.
  • Execute with speed and precision: Drive predictable, data-backed growth by managing pipeline health, conversion rates, and sales productivity.
  • Think like a builder: Continuously improve systems, tools, and playbooks to help the team sell smarter and scale faster.
  • Collaborate to amplify impact: Partner with Marketing, Sales Ops, Partnerships, and Product to align regional execution with national strategy and feedback loops.
  • Inspire and develop talent: Attract, retain, and grow high-performing sales professionals who are hungry to win and advance their careers.
  • Represent Square locally: Serve as the face of Square's brand and mission across key Central markets—connecting with business leaders, partners, and communities.

Qualifications

  • 10+ years of sales experience
  • 5+ years leading regional or field sales teams in a high-growth SaaS, fintech, or payments environment
  • Proven success driving overperformance with track record of exceeding regional revenue and productivity goals
  • Proven track record of building high-performance teams and cultures
  • Strong product acumen with ability to position complex solutions across multiple product lines and use data to guide decisions
  • Builder mindset with ability to move fast and scale
  • Deep operational expertise in forecasting, pipeline management, and KPI tracking
  • Excellent communication and executive presence with ability to influence across all levels of the organization

Skills

Required:Sales leadershipStrategic planningProduct acumen

Benefits

  • Remote work
  • medical insurance
  • flexible time off
  • retirement savings plans
  • modern family planning
Last updated Oct 14, 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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