Head of Square Commercial Operations & Deal Excellence

Block
San Francisco
Workplace: RemoteFull timeUSD 239,600 - 359,400Function: Administration & Executive AssistanceExperience: 10+ yearsSkills: []

Build and lead the commercial operating system powering Square’s global Revenue organization. Own the end-to-end Deal Desk, pricing operations, strategic deal support, and commercial governance—enabling faster, smarter, and more consistent commercial decisions. Partner closely with Finance, Sales, Product, Engineering, Legal, Risk, and Revenue Operations to translate pricing strategy into scalable seller workflows, automate quote-to-cash, and track commercial performance through executive dashboards.

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FursaFursa
Block
Block
1 month ago

Head of Square Commercial Operations & Deal Excellence

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Last checked: 16 hours agoStatus: Live

Job Summary

Build and lead the commercial operating system powering Square’s global Revenue organization. Own the end-to-end Deal Desk, pricing operations, strategic deal support, and commercial governance—enabling faster, smarter, and more consistent commercial decisions. Partner closely with Finance, Sales, Product, Engineering, Legal, Risk, and Revenue Operations to translate pricing strategy into scalable seller workflows, automate quote-to-cash, and track commercial performance through executive dashboards.
Location: San Francisco
Workplace: Remote
Employment Type: Full time
Job Function: Administration & Executive Assistance
Seniority: Sr. Director level

Key Responsibilities

  • •Partner with Finance to operationalize Square’s pricing strategy, commercial policies, and investment guardrails, translating them into scalable seller workflows and decision-support tools.
  • •Lead commercial strategy for Square’s largest and most strategic opportunities, structuring creative solutions and advising executives on complex commercial decisions and investments.
  • •Own the end-to-end operation of Square’s global Deal Desk, including intake, review, approval, booking workflows, SLAs, operating rhythms, and repeatable playbooks.
  • •Modernize Square’s commercial operating model through AI and automation, embedding pricing recommendations and approval logic into seller workflows to improve deal velocity and quote-to-cash.
  • •Monitor and improve commercial performance by tracking pricing/approval trends, discount behavior, deal cycle time, and margin realization; build executive dashboards and evolve governance with Finance, Legal, Product, and Risk.
  • •Build and lead a high-performing global team across Deal Desk, pricing operations, strategic deal support, and commercial excellence.

Pay and Benefits

Salary: USD 239,600 - 359,400
Perks:Remote WorkHealth InsuranceFlexible TimeRetirement SavingsFamily Planning

Key Requirements

  • •10+ years of experience leading Deal Desk, Commercial Operations, Revenue Operations, Sales Strategy, Pricing, Consulting, or related functions.
  • •Experience building and scaling commercial operating systems within SaaS, fintech, payments, or enterprise software.
  • •Deep expertise in enterprise sales, pricing operations, commercial governance, and complex deal structuring.
  • •Proven ability to build scalable operating models, approval workflows, and AI-enabled commercial processes.
  • •Strong analytical and financial acumen with the ability to evaluate complex commercial tradeoffs, plus exceptional cross-functional leadership.
Experience:10+ years
Languages:English
Tech Stack:AIAutomationDashboardsQuote-to-cash

Company Brief

Block
Builds financial services and commerce tools to empower businesses and individuals, operating products such as Square, Cash App, Spiral (Bitcoin initiatives), TIDAL, and developer-focused payment and banking solutions.
Industry: Fintech Infrastructure
Company Size: Enterprise (1,001+ employees)
Revenue: USD 1B+
Growth: Public Company
Valuation: Public Company (Market Cap in USD)
Funding: IPO / Publicly Listed
Headquarters: San Francisco, United States
Founded: 2009
WebsiteLinkedIn