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

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. 

Qualifications

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

Additional Information

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 t