Head of Channel Sales Enablement

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 Head of Channel Sales Enablement will lead the strategic development and execution of learning and development programs that accelerate Channel Sales (Resellers and Independent Contractors) performance across all markets. This role is responsible for managing a team of coaches and trainers, developing sales-led learning content, and optimizing tooling and systems to drive faster ramp times and improved Seller productivity. As Channel Sales motions scale globally, this leader will build and grow the training and coaching function to support expanding business needs.

You Will

Team Leadership & Development

• Manage and develop a team of sales coaches and trainers, providing guidance on coaching methodologies and performance standards.
• Build and scale the enablement team in alignment with Channel Sales growth across markets
• Coordinate activities across the team, ensuring alignment on priorities, methodologies, and success metrics
• Foster a culture of continuous improvement and data-driven decision making within the team

Learning Content & Curriculum Design

• Own the strategy and execution of learning content focused on sales-led approaches for Channel Sales teams
• Design and implement comprehensive onboarding and ongoing development programs that reduce ramp time and improve seller effectiveness
• Partner with key support functions, and other stakeholders to ensure content reflects current go-to-market strategies and product positioning
• Establish frameworks for content creation, quality standards, and regular updates to keep pace with market changes

Tooling, Systems & Process Optimization

• Define requirements for and manage learning technology stack, including learning management systems, coaching platforms, and performance analytics tools
• Work cross-functionally to integrate learning systems with sales tools and CRM to create seamless seller experiences
• Establish measurement frameworks and KPIs to track learning effectiveness, ramp time improvements, and business impact
• Identify and resolve systemic barriers to seller productivity through process improvements and tool optimization

Strategic Planning & Execution

• Develop and execute multi-quarter roadmaps aligned with Channel Sales strategic objectives
• Analyze complex learning challenges across diverse markets, evaluating variable factors such as regional differences, product complexity, and Seller segmentation
• Exercise judgment in selecting methods, techniques, and evaluation criteria for program design and delivery
• Recommend and implement changes to enablement policies and procedures that affect the broader sales organization

Cross-Functional Collaboration & Influence

• Network with key functions across Sales, Marketing, Product, Operations, and other functions to ensure learning initiatives support business priorities
• Lead cooperative efforts among cross-functional teams to design and launch new Channel Sales programs
• Frequently interact with senior sales leadership and functional peer groups on matters concerning learning strategy, resource allocation, and performance outcomes
• Gain acceptance and drive adoption of learning programs across geographically distributed teams

You Have

Experience & Background

• Minimum of 8 years experience working in a FinTech or the payments industry at a leadership level
• Proven track record in sales enablement, sales training, or sales operations roles with increasing scope and responsibility
• Experience managing teams and coordinating activities across multiple geographies or business units
• Deep understanding of sales methodologies, adult learning principles, and enablement best practices
• Experience with channel sales or partner ecosystems strongly preferred

Skills & Competencies

• Strategic Thinking: Ability to translate business objectives into comprehensive enablement strategies and execution plans
• Leadership: Demonstrated capability to manage, develop, and scale high-performing teams
• Analytical Rigor: Strong data analysis skills to measure program effectiveness, identify trends, and make data-driven recommendations
• Cross-Functional Influence: Proven ability to lead without direct authority, building consensus and driving outcomes across diverse stakeholder groups
• Communication: Excellent written and verbal communication skills, with ability to present to senior leadership and gain buy-in for initiatives
• Execution Excellence: Track record of delivering complex programs on time and achieving measurable business results
• Adaptability: Comfortable working in fast-paced, evolving environments with changing priorities

Technical Knowledge

• Wide-ranging experience with enablement technologies (LMS, coaching platforms, analytics tools)
• Understanding of sales tools and CRM systems (e.g., Salesforce)
• Familiarity with content development tools and learning design methodologies
• Ability to leverage data and analytics to inform decision-making

Location & Travel

• This role may require travel to support enablement programs across multiple markets (travel percentage to be determined based on business needs)

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. Want to learn more about what we're doing to build an inclusive workplace? Check out our Inclusion & Diversity page