Sales Training Manager

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.

The Role

The Sales Engineering Specialist will help accelerate Gross Processing Volume (GPV) and revenue growth globally by supporting our Resellers in their efforts to acquire, retain, and expand seller use cases.

This role drives impact in two key ways:

1. Direct Reseller Support – Being a product expert, co-selling with Resellers, handling seller escalations, and recommending first- and third-party solutions that drive immediate GPV and revenue growth.


2. Strategic Insights & Enablement – Partnering with cross-functional teams (Product, Partnerships, Marketing, Enablement) to identify market opportunities, analyze product gaps, and inform long-term go-to-market strategy.

As a generalist Product Specialist, you will support sellers across the entire Square ecosystem and in all the industries we serve. You will work closely with our Resellers, and internal stakeholders to grow Square's presence globally.

Why Join?

As a member of the team, you will play an essential role in shaping Square's presence globally. You'll work at the intersection of Sales, Product, Marketing, and Partnerships—helping sellers grow their businesses while driving strategic impact. If you thrive in a dynamic, collaborative environment and are passionate about helping businesses succeed, we'd love to hear from you!

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, based solely on the core competencies required of the role at hand, and without regard to any 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.

Time allocation:

• 50% Reactive - Co selling, Product Demonstrations etc.


• 50% Proactive - Product Training, Installation and go-live Training etc


• (Significant Travel Required)

You Have

• 3-5 years of experience in Sales, Account Management, or a similar client-facing role.


• Consistent overachievement of goals and objectives.


• Experience with product development and an analytical approach to identifying market opportunities.


• Strong written and verbal communication, with the ability to simplify complex concepts for different audiences.


• Ability to manage multiple projects simultaneously while maintaining high attention to detail.


• Deep understanding of the ISO/Reseller community


• Capacity to assess business opportunities, understand buyer needs, and position Square effectively against competitors.


• Ability to collaborate cross-functionally and work with internal and external stakeholders to drive outcomes.


• Openness to feedback and a commitment to continuous improvement.


• Comfortable navigating changing situations and thinking quickly on your feet.