Head of Finance & Strategy, Square GTM

  • Full-time

Company Description

Since we opened our doors in 2009, the world of commerce has evolved immensely, and so has Square. After enabling anyone to take payments and never miss a sale, we saw sellers stymied by disparate, outmoded products and tools that wouldn’t work together.

To solve this problem, we expanded into software and built integrated solutions to help sellers sell online, manage inventory, book appointments, engage loyal buyers, and hire and pay staff. Across it all, we’ve embedded financial services tools at the point of sale, so merchants can access a business loan and manage their cash flow in one place. Afterpay furthers our goal to provide omnichannel tools that unlock meaningful value and growth, enabling sellers to capture the next generation shopper, increase order sizes, and compete at a larger scale.

Today, we are a partner to sellers of all sizes – large, enterprise-scale businesses with complex operations, sellers just starting, as well as merchants who began selling with Square and have grown larger over time. As our sellers grow, so do our solutions. There is a massive opportunity in front of us. We’re building a significant, meaningful, and lasting business, and we are helping sellers worldwide do the same.

Job Description

The role

Go-to-market (GTM) is the engine that empowers Square’s growth. Our GTM motion encompasses our Marketing, Sales, Account Management, Customer Success and Hardware functions. Across GTM we invest nearly a half billion dollars annually to enable acquisition of all types of customers (“sellers”). We have a long track record of success highlighted by consistent, strong returns as we’ve evolved our growth efforts into new channels, new markets and new seller segments.  

We are looking for a finance executive to run our Finance & Strategy GTM organization. In this role you will partner with the CEO of Square and her executive GTM team to (1) help design and execute our marketing strategy, (2) identify, assess and drive investment strategy and growth opportunities, (3) lead and scale a growing finance organization to drive excellent results for the business. At Square, Finance & Strategy’s mandate is to drive financial and operational decision-making. Our team’s core value is trust – we build it by making what is complex simple, and we do it with analysis that is accurate and easy-to-understand. Partners rely on our insights and trust us to help solve all problems - both big and small. We believe good ideas can come from anywhere, and we’ll rely on you to work with others, form intelligent opinions, and present your thoughts to decision-makers and company executives. 

This position can sit in any US Block office or be 100% remote from any US state with the exception of Alaska.

You will: 

  • Report to the Head of Square Finance & Strategy (Square CFO)
  • Oversee the GTM finance organization of over twenty-five people. You will grow and scale the existing team as well as hire, mentor and retain top talent 
  • Partner with the Square CEO, Head of Square Marketing, Head of Square Sales/AM, Head of Square Customer Success and Head of Square Hardware to build and unify the strategies behind our Square GTM motion. Critical to success in this role will be your ability to work cross functionally with these and other senior stakeholders
  • Drive Square’s investment strategy across GTM functions and channels, building frameworks to measure outputs and success and to assess trade-offs across investment opportunities. Success will be measured not only on your ability to help create and execute a unified investment strategy but also on the growth performance of the business
  • Lead and execute all of the financial, strategic and planning processes supporting our GTM activities including monthly / quarterly performance reviews, Annual Plan and Long Range Planning activities
  • Create / delivery strategy for pricing, customer acquisition incentives, revenue attainment forecasting, headcount investment, SLA and SEV remuneration, custom pricing management, sales incentives
  • Program and project manage OKRs to deliver near and long term success for the business
  • Drive process excellence in the work of your team and partners, including: (1) overseeing organization-wide planning cycles with complex multiple stakeholder dependencies, (2) work with our Business Intelligence teams to build new metrics and tools for measuring and reporting KPIs and business performance, (3) drive increased efficiency in the processes and output of the F&S GTM team   
  • Work closely with our Data Science teams to assess / review efficacy of our unified attribution models, incrementally measurement and ROI projections


  • At least 15+ years of relevant experience in marketing/sales investment, finance and strategy creation & execution
  • Experience running and scaling large finance organizations, including building and maintaining a high-performing team through hiring and coaching
  • Served as a trusted advisor and partner to senior executives; advising on company-level strategy initiatives and investment decisions that have enabled company-wide growth
  • Excellent problem solving skills and a track record of delivering results on corporate wide initiatives
  • The ability to distill complex information into clear problem statements that can be systematically analyzed and communicated; frames both approaches and solutions in a way that is actionable for all audiences
  • Comfort working with metrics, building new KPIs and navigating large data sets to find answers to complex problems
  • Commitment to Square’s purpose of Economic Empowerment

Additional Information

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

Zone A: USD $296,600 - USD $362,500
Zone B: USD $296,600 - USD $362,500
Zone C: USD $296,600 - USD $362,500
Zone D: USD $296,600 - USD $362,500

To find a location’s zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information. 

Benefits include the following:

  • Healthcare coverage
  • Retirement Plans including company match 
  • Employee Stock Purchase Program
  • Wellness programs, including access to mental health, 1:1 financial planners, and a monthly wellness allowance 
  • Paid parental and caregiving leave
  • Paid time off
  • Learning and Development resources
  • Paid Life insurance, AD&D. and disability benefits 
  • Perks such as WFH reimbursements and free access to caregiving, legal, and discounted resources 

This role is also eligible to participate in Block's equity plan subject to the terms of the applicable plans and policies, and may be eligible for a sign-on bonus. Sales roles may be eligible to participate in a commission plan subject to the terms of the applicable plans and policies. Pay and benefits are subject to change at any time, consistent with the terms of any applicable compensation or benefit plans.

We’re working to build a more inclusive economy where our customers have equal access to opportunity, and we strive to live by these same values in building our workplace. Block is a proud equal opportunity employer. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, veteran status, pregnancy, gender expression or identity, sexual orientation, citizenship, or any other legally protected class. 

We believe in being fair, and are committed to an inclusive interview experience, including providing reasonable accommodations to disabled applicants throughout the recruitment process. We encourage applicants to share any needed accommodations with their recruiter, who will treat these requests as confidentially as possible. Want to learn more about what we’re doing to build a workplace that is fair and square? Check out our I+D page.

Additionally, we consider qualified applicants with criminal histories for employment on our team, assessing candidates in a manner consistent with the requirements of the San Francisco Fair Chance Ordinance.


Block, Inc. (NYSE: SQ) is a global technology company with a focus on financial services. Made up of Square, Cash App, Spiral, TIDAL, and TBD, we build tools to help more people access the economy. Square helps sellers run and grow their businesses with its integrated ecosystem of commerce solutions, business software, and banking services. With Cash App, anyone can easily send, spend, or invest their money in stocks or Bitcoin. Spiral (formerly Square Crypto) builds and funds free, open-source Bitcoin projects. Artists use TIDAL to help them succeed as entrepreneurs and connect more deeply with fans. TBD is building an open developer platform to make it easier to access Bitcoin and other blockchain technologies without having to go through an institution.

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