Head of Sales Strategy & Operations

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.

Role Purpose:

The Head of Sales Strategy & Ops is responsible for enabling and executing the expansion of channel programmes into new markets. This role sits at the intersection of strategy, product, and operations, ensuring that channel expansion is commercially viable, competitively differentiated, compliant with local regulations, and operationally ready for launch.

The role will lead market research and competitor analysis to inform pricing, proposition design, and go-to-market decisions, while working cross-functionally to ensure all operational, regulatory, and legal requirements are met. The successful candidate will be highly commercially minded, product-driven, and focused on delivering measurable results.

Key Responsibilities:

Market Expansion & Strategy

• Own the operational and strategic readiness for expanding channel programmes into new markets


• Assess market attractiveness and prioritise expansion opportunities based on commercial potential, competitive landscape, and operational feasibility


• Develop market entry assessments and business cases to support expansion decisions

Market Research & Competitive Analysis

• Conduct detailed market research to understand customer needs, channel dynamics, and local market conditions


• Analyse competitor offerings, pricing models, incentives, and positioning to inform differentiated channel propositions


• Translate insights into clear recommendations for pricing, proposition design, and programme structure

Pricing & Proposition Development

• Partner with Channel Sales, Product, and Finance to define market-appropriate pricing and commercial models


• Ensure channel propositions are aligned with product capabilities, customer value, and revenue objectives


• Support the evolution of channel programmes based on market feedback and performance data

Regulatory, Legal & Compliance Readiness

• Identify regulatory, legal, and compliance requirements for new markets in partnership with Legal, Risk, and Compliance teams


• Ensure channel programmes meet all local market requirements prior to launch


• Proactively surface risks and dependencies that could impact market entry timelines

Operational Readiness & Execution

• Coordinate cross-functional readiness across Product, Sales, Operations, Finance, Legal, and Enablement teams


• Ensure processes, tools, documentation, and support models are in place to successfully operate in new markets


• Drive execution against launch timelines, resolving blockers and ensuring accountability

Performance & Results Focus

• Define success metrics for market expansion initiatives and track performance post-launch


• Use data and insights to recommend optimisations to channel programmes and operational models


• Maintain a strong outcomes-driven mindset, balancing speed, quality, and commercial impact

Stakeholder Management

• Act as a key partner to Channel Sales leadership, providing strategic and operational insights


• Influence cross-functional teams without direct authority to deliver expansion objectives


• Communicate clearly and confidently with senior stakeholders on progress, risks, and results

Skills & Experience

Essential

• Proven experience in strategy, operations, commercial planning, or channel-related roles


• Strong commercial acumen with the ability to evaluate market opportunities and financial trade-offs


• Experience conducting market research and competitor analysis to inform strategic decisions


• Demonstrated ability to work cross-functionally in complex, fast-moving environments


• Product-driven mindset with a focus on customer value and measurable outcomes


• Strong analytical skills with the ability to turn insight into action

Desirable

• Experience supporting market entry or international expansion initiatives


• Familiarity with channel sales models, partner programmes, or indirect distribution


• Exposure to regulatory or compliance considerations across multiple markets


• Experience working in technology, payments, financial services, or platform-based businesses

Personal Attributes

• Commercially curious and results-oriented


• Structured thinker who thrives in ambiguity


• Highly organised with strong attention to detail


• Confident communicator who can influence at multiple levels


• Proactive, ownership-driven, and comfortable operating independently

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 an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and “fair chance” ordinances. 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.