Tooling Strategy Head (Customer Success, Sales, and Account Management)

  • 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.

So we expanded into software and started building integrated, omnichannel solutions – to help sellers sell online, manage inventory, offer buy now, pay later functionality through Afterpay, 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 Growth Data & Strategy team is responsible for building the vision, driving data-driven programs, and defining tooling strategies to increase Sales, Customer Success (CS), and Account Management (AM) teams’ efficiency and effectiveness and improve the experience of businesses that use Square’s ecosystem of products. 

In this role, you will lead a team of Technical Program Managers that support Sales, CS, and Account Management teams in tooling and system decisions, as well as tooling focused project execution. Your team will identify technology opportunities, help define the tooling vision, streamline tech stack, scope solutions, assess trade-offs & risks, align cross-functional stakeholders, and drive execution of programs in partnership with Engineering, and Product Teams. 

With offices in the US, Canada, Japan, Ireland, Australia, Poland, Taiwan, and Guatemala, our goal is to improve both quality of the operations, increase cost efficiency, while fostering innovative solutions (e.g. GenAI). You will report to the Head of Growth Data and Strategy. 

You Will: 

  • Manage a team of Technical Program Managers (both ICs and leads) who are responsible for designing, documenting, building, and executing on essential strategic system/infrastructure programs to propel the Sales, CS, and Account Management organizations towards realizing our global vision and strategy

  • Become an expert on our business processes and technology platforms ecosystem

  • Build the tooling and system vision for Sales, CS, and Account management

  • Manage portfolio of tooling projects to achieve above vision

  • Propose wide-sweeping improvements to our infrastructure/tools suite through automation and redesign

  • Use your understanding of software development processes to identify dependencies, "long poles," “blockers,” and execution risks and develop mitigation strategies.

  • Ensure smooth operations of the global Sales, AM, and CS population regarding our tools and infrastructure suite. Work with our systems, engineering, and technology partners to refine our governance/operating model, holding each team accountable for system uptime (measurement and timely reporting) and delivery of new capabilities

  • Provide leadership oversight to ensure that – across all of the programs we're working on throughout the organization and with our cross-functional stakeholders – we are prioritizing our work and resources effectively, measuring impact, and delivering results

  • Develop deep, mutually-beneficial working relationships with various partners and stakeholders, including: internal product & engineering teams

  • Participate in annual and quarterly planning between business partners, Finance, systems, engineering, and technology partners


You have:

  • 8+ years of experience in technical project/program management, product management, or software engineering; 3+ years of experience building and managing a team

  • Ability to set the tooling and system vision for multiple organizations, achieving improvement in operational efficiency, and quality of operations

  • Knowledge of Sales, AM, Customer Success or similar contact center engineering landscapes

  • Knowledge of Go To Market motion

  • Experience in collaborating with engineering and product organizations for end-to-end design and implementation of technical solutions

  • Experience documenting business and technical requirements (i.e. writing Product Requirements Documents) – ready for project execution

  • The ability to establish and run a governance model across multiple cross-functional stakeholders (including engineering organizations)

  • Experience communicating and translating non-technical to technical (and vice versa) requirements and discussions, organizational, coordination, and running multiple projects

  • The ability to manage multiple projects simultaneously, often with competing resources.

  • A keen eye for prioritization and continuous optimization. You have the ability to discern the urgency and importance of work. You find creative ways to use the full potential of our existing tools, and advocate for novel solutions

  • The ability to analyze data to identify the largest strategic opportunities for the organization. Be able to use data-driven insights to provide high-impact recommendations 

  • Experience with Salesforce, Amazon Web Services, JIRA, SQL and Looker is a plus!

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 $180,000 - USD $270,000
Zone B: USD $171,000 - USD $256,600
Zone C: USD $162,000 - USD $243,000
Zone D: USD $153,000 - USD $229,600

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. 

Full-time employee benefits include the following:

  • Healthcare coverage (Medical, Vision and Dental insurance)
  • Health Savings Account and Flexible Spending Account
  • 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 (including 12 paid holidays)
  • Paid sick leave (1 hour per 26 hours worked (max 80 hours per calendar year to the extent legally permissible) for non-exempt employees and covered by our Flexible Time Off policy for exempt employees) 
  • Learning and Development resources
  • Paid Life insurance, AD&D, and disability benefits 

These benefits are further detailed in Block's policies. 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.

While there is no specific deadline to apply for this role, on average, U.S. open roles are posted for 70 days before being filled by a successful candidate.

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