Enablement Program 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

We're looking for an Enablement Program Manager to join our Sales Onboarding team and lead onboarding and ramp enablement for Square’s AU sales reps (SDRs, BDRs, AEs, AMs, and Field Sales AEs). This role will own the strategy, design, and execution of scalable, new hire enablement programs for teams responsible for acquiring new sellers and retaining and growing existing sellers.

You’ll collaborate closely with Sales Leadership, Sales Ops, Product Marketing, and cross-functional partners to ensure reps are equipped with the knowledge, tools, and training needed to succeed in a complex, fast-paced sales environment.

You Will

• Design and implement a 30/60/90-day onboarding experience tailored to each sales motion, blending live instruction, digital content, lead coaching, and in-field application.


• Partner with Sales Leadership to define success metrics, identify capability gaps, and continuously evolve new hire training content based on rep performance and business needs.


• Create and manage new hire assets such as playbooks, certification programs, and manager toolkits.


• Collaborate with Program Managers, Enablement peers, and cross-functional stakeholders to ensure onboarding content is up-to-date, accessible, and globally aligned.


• Analyze program effectiveness using data and feedback loops; adjust training plans and rollout strategies accordingly.

You Have

• 4+ years in Sales and/or Sales Enablement Program Management or Learning & Development supporting outbound sales teams.


• Deep understanding of how to build and scale onboarding programs that reflect real-world sales processes and scenarios.


• Strong instructional design instincts with the ability to convert strategic objectives into tactical learning.


• Excellent project management skills; comfortable aligning multiple stakeholders across Sales, Ops, and Product teams.