Scaled Seller Onboarding Enablement Lead

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, 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.

About the role

Square is looking for an enablement expert to help sellers get started, train their teams, and confidently use our products. You’ll bring deep product and services expertise into our onboarding operation, building programs that help employees, third-party providers, and sellers succeed at scale.

You’ll work across three connected areas: internal team enablement, seller education, and third-party training and coaching. You should be exceptional at teaching a seller one-to-one, coaching an onboarding specialist, or helping a service provider navigate a complex setup. Your primary impact, however, will come from turning that expertise into repeatable programs, practical tools, and consistent training standards—not personally delivering every session.

This is an individual contributor role within Global Onboarding Operations. You’ll partner with onboarding leaders, Product, Sales, Support, and customer education teams to connect product knowledge with how onboarding is delivered. You’ll stay close to sellers and frontline teams, then use what you learn to improve how the broader operation teaches, coaches, and supports them.

What you’ll do

Turn product expertise into scalable enablement

• Develop deep expertise in Square’s products, onboarding services, and common seller workflows, including configuration, hardware setup, and getting ready to transact.
• Translate product capabilities and technical concepts into practical guidance tailored to different business types, roles, and levels of experience.
• Identify recurring knowledge and skill gaps through seller interactions, training observations, quality reviews, and frontline feedback.
• Turn those insights into reusable training modules, demonstrations, facilitator guides, job aids, and coaching resources.
• Establish ways to keep enablement materials accurate as products and services evolve.

Strengthen internal onboarding teams

• Design and improve onboarding, ongoing learning, and product-readiness programs for employees who help sellers get started.
• Build role-based learning paths that develop both product proficiency and the ability to teach sellers effectively.
• Create practice scenarios, knowledge checks, and skill assessments that test whether employees can apply what they’ve learned.
• Equip managers and team leads with coaching tools, observation rubrics, and clear standards for effective seller training.
• Support complex training needs directly when appropriate, then turn the lessons into resources others can use.

Improve seller training

• Shape training approaches that help sellers complete setup, understand relevant features, and prepare their teams to use Square.
• Develop reusable agendas, demonstrations, exercises, and follow-up materials for individual training, group sessions, and webinars.
• Deliver selected seller sessions to test new approaches, understand learning needs, and model high-quality facilitation.
• Partner with the self-service onboarding team to bring product expertise and frontline insights into digital learning content.
• Connect live and self-service learning so sellers receive consistent guidance and can continue learning after a session ends.

Build third-party training and coaching programs

• Create training and readiness programs for third-party providers delivering onboarding, installation, or seller education.
• Develop train-the-trainer programs so partners can build capability within their own teams.
• Establish practical standards for product knowledge, demonstration skills, seller communication, and training quality.
• Use session observations, assessments, and seller feedback to identify coaching needs and improve partner delivery.
• Partner with vendor operations leaders to make training, refresher learning, and readiness checks part of ongoing partner management.

Drive adoption and measure effectiveness

• Own enablement initiatives from needs assessment through design, pilot, rollout, and continuous improvement.
• Coordinate subject matter experts and cross-functional contributors without relying on direct reporting authority.
• Measure success through demonstrated proficiency, time to readiness, training quality, reduced rework, and seller onboarding outcomes—not attendance alone.
• Use AI-assisted tools where they improve content creation, practice, or knowledge access, with appropriate accuracy checks and human review.
• Prioritize programs that address recurring needs and help more people deliver effective onboarding independently.

What you’ll bring

• Significant experience in product enablement, customer education, technical training, implementation, or a related field.
• A track record of turning hands-on product expertise into training programs, tools, and systems used across teams or partner networks.
• Strong instructional design skills, including adult learning principles, curriculum development, practice-based learning, and assessment.
• Exceptional facilitation and coaching skills, with experience teaching customers and adapting your approach to different levels of technical confidence.
• The ability to learn complex software and service offerings deeply, explain them clearly, and connect them to real business workflows.
• Experience building train-the-trainer programs, facilitator resources, and coaching frameworks that enable others to teach effectively.
• Hands-on experience creating learning modules, product demonstrations, videos, job aids, and knowledge resources.
• Strong program management skills, including prioritization, stakeholder coordination, launch planning, and content maintenance.
• The ability to use performance data and qualitative feedback to distinguish training needs from product, process, or tooling issues.
• Experience leading cross-functional work independently and gaining adoption without direct authority.

Additional experience we’d value

• Expertise in Square products or experience with payments, commerce, point-of-sale systems, or business software.
• Training that combines software configuration, hardware setup, and operational workflows.
• Enablement programs for outsourced teams, implementation partners, or field service providers.
• Experience supporting a high-volume sales and onboarding environment.
• Familiarity with learning management systems, content authoring tools, knowledge platforms, and learning analytics.
• Experience adapting training across markets, languages, or delivery channels.

Why this role matters

A strong onboarding experience depends on more than knowing the product. It requires people who can teach it well—and programs that make that expertise available consistently.

You’ll help turn individual product knowledge into shared capability, giving employees, third-party providers, and sellers the tools and confidence to put Square to work.