IT Strategy and Portfolio Management Office Lead

  • San Francisco, CA
  • Full-time

Company Description

When we launched the little white reader, we invented mobile, ubiquitous payments and enabled anyone to start, run, and grow a business. Ten years and billions of transactions later we’re reimagining commerce for businesses of all types and sizes—we’re enabling the independent electrician to send invoices, helping the beauty salon pay its employees, and giving the burgeoning coffee chain capital for a second, third, and fourth location. We’re working to find new and better ways to help businesses succeed on their own terms—and we’re looking for people like you to help shape tomorrow at Square.

Job Description

Join our growing Business Technology team as we empower business to achieve our next chapter of global growth and scale with a digital and distributed workforce. We are seeking a strategic, innovative, pragmatic player-coach leader to establish and manage the strategic vision of the IT project portfolio in support of the Company’s growth.

The Head of IT Strategy and Portfolio Management is accountable for the planning, execution, and monitoring of the overall IT project portfolio.  This individual will establish and directly manage a Program Management Office (PMO). This leader will drive PMO best practices to ensure quality in PMO related data, process, and solutions.  The ideal candidate will possess a strong sense of ownership, deep knowledge of planning practices, and broad PMO experience. At Square we do IT differently, we focus on exceptional employee experience and technology innovation.  This position reports to the Head of Business Technology and is based out of San Francisco CA or Oakland CA.    

You will: 

  • Understand and translate business strategy into an aligned IT strategy and portfolio of programs, projects and applications.

  •  Partner and collaborate with key Biz Tech staff of other Square divisions to support cross functional business initiatives, and explore IT synergies and efficiencies.

  • Create and implement IT planning practices that help Business Technology deliver the highest value for Square employees

  • Collaborate with key business and IT decision makers to identify IT projects that align with business priorities

  • Connect planning practices to long term strategic roadmaps

  • Lead and mentor program managers focusing on execution excellence and career growth

  • Foster a business-oriented team culture and mindset

  • Clearly define the priorities of the PMO and manage resource allocation effectively

  • Lead the continuous improvement of  PMO methodologies, standards, tools, and policies

  • Act as a trusted advisor to build and maintain empowered partnerships with IT and business leaders

  • Foster a lean portfolio management and agile project management environment

  • Manage portfolio level activities like change control, portfolio health reviews, and planning processes

  • Identify trends and opportunities to improve the management of project financials, timelines, resources, and delivery quality

  • Work with the various IT teams to establish key performance metrics, and measurements are implemented to predictable delivery of technology solutions and ensure continuous improvement is established

  • Oversee IT technology communications including internal comms regarding technology initiatives and organizational comms.

  • Manage execution of complex cross functional programs.

  • Overall budget management for Business Technology group.


You have:

  • 15+ years of IT experience

  • 5-10 years experience with project portfolio and planning experience, IT management, and program management

  • Bachelor’s degree in Information Systems, Computer Science, or other related technical degree or equivalent work experience

  • Track record of establishing credibility with senior executives and technical and non-technical team members

  • Ability to attract, retain and develop high caliber program managers

  • Strong organizational and project management skills

  • Hands-on leadership experience and can provide direct guidance to program managers

  • Deep understanding of planning, portfolio management, and program management methodologies

  • Experience defining and managing a KPI oriented and value based planning process

  • Excellent verbal and written communication skills 

  • PMP certification is a plus

  • Experience implementing SaaS solutions

Additional Information

At Square, our purpose is to empower – within and outside of our walls. In order to build the best tools for the businesses and customers we support all over the world, we have to start at home with a workforce as diverse and empowered as our sellers. To this end, we take great care to evaluate all employees and job applicants equally, based on merit, competence, and qualifications. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, disability status, or any other characteristic protected by law. We encourage candidates from all backgrounds to apply and always consider qualified applicants with arrest and conviction records, in accordance with the San Francisco Fair Chance Ordinance. Applicants in need of special assistance or accommodation during the interview process or in accessing our website may contact us by sending an email to assistance(at) We will treat your request as confidentially as possible. In your email, please include your name and preferred method of contact, and we will respond as soon as possible. Perks At Square, we want you to be well and thrive. Our global benefits package includes: Healthcare coverage, Retirement Plans, Employee Stock Purchase Program, Meal reimbursements, Wellness perks, Paid parental leave, Flexible time off, Learning and Development resources