Professional Services, Lead

  • San Francisco, CA
  • Full-time

Company Description

We believe the economy is better when everyone has access. When everyone has room to grow. No one should be left out because the cost is too great or the technology too complex. We started with a little white credit card reader but haven’t stopped there. We’re empowering the independent electrician to send invoices, setting up the favorite food truck with a delivery option, helping the ice cream shop pay its employees, and giving the burgeoning coffee chain capital for a second, third, and fourth location. We’re here to help sellers of all sizes start, run, and grow their business—and helping them grow their business is good business for everyone.

Job Description

Square is looking for a passionate leader to develop and manage our US-based Professional Services Team. The Square Professional Services team leverages strong project management skills and industry knowledge to onboard Square’s largest and most complex customers using a number of different strategies: on-site training, partnerships, and scalable onboarding. You will be responsible for planning, organizing, and leading a 15-person Professional Services organization that is a part of the Square Sales organization. Your leadership will directly help Square drive revenue by scaling and refining our customer onboarding program. Your work will accelerate the Sales funnel, drive efficiency and automation in onboarding, while providing the best experience to Square customers. This role reports directly to our Head of SMB Sales in San Francisco.

You will:

  • Create the vision for Professional Services team growth in our San Francisco, New York, St. Louis and other offices and help our Professional Services Managers execute in tandem with their teams.

  • Deliver on expected levels of customer onboarding productivity as determined by the Sales model.

  • Scale and refine our customer onboarding program, driving efficiency and automation, while finding additional monetization opportunities across the organization.

  • Partner in cross-functional efforts across Sales, Sales Ops, Account Management, Customer Success, Product, Marketing, and Finance to remove obstacles, drive customer adoption and create an optimal customer experience.

  • Manage and develop 2 frontline Managers while leading and mentoring 2 teams of Professional Services Associates.

  • Exhibit a growth mindset; be proactive and entrepreneurial, fail fast and learn.


You have:

  • 6+ years of success across Sales, Professional Services and/or Operations.

  • 3+ years of success in a Sales/Professional Services/Operations Leadership role with experience leading a team of frontline managers and a proven track-record of business growth.

  • BA/BS Degree preferred.

  • Project/Program Management experience.

  • Experience in high transaction volume SaaS application or financial services Sales preferred.

  • Proven ability to work with and influence cross-functional teams and departments in a rapidly growing environment.

  • Excellent interpersonal, leadership, organizational, and communication skills.

  • Extensive experience in a metrics-driven Sales organization.

  • Strong ability to coach your Managers and Associates to higher performance (outputs and customer experience).

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.