Customer Success Automation Manager

  • Full-time
  • Alternate Location: New York, United States

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.

To solve this problem, we expanded into software and built integrated solutions to help sellers sell online, manage inventory, 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

Square's Customer Education Team equips sellers with technical product resources and foundational business knowledge, empowering them to independently navigate how to start, run, and grow the business of their dreams. Our simple, straightforward, and accurate content empowers Sellers with innovative learning experiences to build foundational product, technical, and business knowledge for sustained long-term growth. We answer questions while simultaneously teaching business owners how to maximize their use of Square.

As the Automation Specialist Lead you will champion customer success automations, increase self-service adoption, and improve Square's pre-contact experience. You will manage the performance of a growing team of Automation Specialists and launch automated experiences to support, troubleshoot and educate sellers through Square's ecosystem of products and services. On top of building a team, the Automation Specialist Lead will drive team results through active analysis of chatbot performance and work with several cross-functional partners across CS, Engineering, Onboarding, Marketing, Product, Localization, Compliance, Legal and Communications. This position will report to the Global Lead of Customer Education.

You Will:

  • Manage and measure a growing team of Automation Specialists, ensuring automation content is accurate and up-to-date.

  • Define automation team workflows, establish project timelines, implement process improvements, and draft improvement project proposals with key stakeholders.

  • Set the automation roadmap and drive ongoing improvement projects to the automated support experience.

  • Identify automation successes and areas of opportunity for the automated support experience, promoting the work of the automation team.

  • Surface trends in the seller support experience to help inform key changes, improvements, and experiences to drive automation KPIs.

  • Maintain in-depth technical knowledge of automation platform(s) workflows, dependencies, and limitations.


You Have:

  • 2+ years relevant experience leading technical, customer-facing teams with measurable results or 5+ years of automation writing experience with examples of launching large projects, measurable results, and improvements to content launch workflows.

  • Strong drive and proven ability to develop direct reports and others.

  • Experience influencing critical decisions within cross-functional organizations without direct authority.

  • Strong command skill and ability to confront team and cross-functional partners to hold them accountable to documented expectations.

  • Ability to be creative and strategic.

  • Strong project management and time management skills.

  • Interpersonal skills with a keen ability to explain complex concepts across the organization and to large audiences.

  • Scaled work to International markets is a plus

  • Experience developing conversational chatbots is a plus

Additional Information

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, 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, 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

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.

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