Senior Customer Success Manager, Technical Support

  • Chicago, IL, USA
  • Employees can work remotely
  • Full-time
  • Alternate Location: Salt Lake City, United States

Company Description

Square builds common business tools in unconventional ways so more people can start, run, and grow their businesses. When Square started, it was difficult and expensive (or just plain impossible) for some businesses to take credit cards. Square made credit card payments possible for all by turning a mobile phone into a credit card reader. Since then Square has been building an entire business toolkit of both hardware and software products including Square POS, Square Stand and more. 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

On Customer Success, our mission is to turn questions into commerce; time is the most precious resource for business owners, and every minute our sellers spend struggling is a minute that could be used to bring about economic change for themselves and their communities. Technical issues, such as hardware defects or bugs in our software, can be especially painful -- interrupting our sellers’ business operations and, in extreme cases, preventing them from accepting payments. 


We are seeking a purpose-driven leader, with an analytical mindset and an aptitude for process improvement, to elevate our Technical Support program. As the Head of Technical Support, you will lead a team of senior Customer Success Specialists and ensure the white-glove resolution of technical issues. You will set the vision and strategy for the program: building out world-class operations, driving customer satisfaction, and promoting employee success. In addition to leading your team to greatness, you will inspire greatness across the organization by using your team’s data and insights to analyze, communicate, and resolve high-impact opportunities to improve the customer experience. 

You will:

  • Coach and mentor team members, with a focus on professional development and instilling a sense of pride and purpose in our work
  • Establish the vision and strategy for Square’s Technical Support program, creating an inspirational and actionable roadmap that answers the question “where are we going and how will we get there?”
  • Implement and improve standard operating procedures, creating highly efficient workflows that enable great customer outcomes
  • Define and implement KPIs, ensuring we have meaningful measures of success for individual contributors and the holistic Technical Support program
  • Introduce regular reporting on technical issues, providing quantitative and qualitative data on the trends and impact of products defects and bugs to stakeholders across the organization
  • Address opportunities to improve skills and knowledge of Technical Support Specialists and frontline Advocates (agents) to drive first-contact-resolution and reduce erroneous escalations 
  • Serve as a consultant and collaborator with product development and operational teams, influencing cross functional roadmaps and go-to-market plans with the customer experience in mind


  • 5+ years relevant professional experience, with at 2+ years of experience leading others
  • Extensive experience in process improvement and change management
  • Excels at data visualization (Looker, Tableau, etc) and analysis (cost/benefit, root-cause, etc.)
  • Excellent written and verbal communication skills
  • Ability to effectively influence and communicate at all levels of an organization
  • Top-notch problem-solving and decision-making abilities
  • Deep commitment to economic empowerment, with a passion for the customer experience

Even Better:

  • Experience building and scaling escalation teams (Help Desk, Tier 2, Tier 3, Advanced Support, Technical Support, etc.)
  • Experience and/or certifications in process improvement methodologies (Lean, Six Sigma, Kaizen, etc.)

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. 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.


At Square, we want you to be well and thrive. Our global benefits package includes:

  • Healthcare coverage
  • Retirement Plans
  • Employee Stock Purchase Program
  • Wellness perks
  • Paid parental leave
  • Flexible time off
  • Learning and Development resources

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. Square 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, 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.

Additionally, we consider qualified applicants with criminal histories for employment on our team, and always assess candidates on an individualized basis.


We want you to be well and thrive. Our global benefits package includes:

  • Healthcare coverage
  • Retirement Plans
  • Employee Stock Purchase Program
  • Wellness perks
  • Paid parental leave
  • Paid time off
  • Learning and Development resources

Square, Inc. (NYSE: SQ) builds tools to empower businesses and individuals to participate in the economy. Sellers use Square to reach buyers online and in person, manage their business, and access financing. Individuals use Cash App to spend, send, store, and invest money. And TIDAL is a global music and entertainment platform that expands Square's purpose of economic empowerment to artists. Square, Inc. has offices in the United States, Canada, Japan, Australia, Ireland, Spain, Norway, and the UK.

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