Head of Sales Strategy & Operations

Block•New York, NY

About The Position

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.

Requirements

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
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

Nice To Haves

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

Responsibilities

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
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
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
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
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
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
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

Benefits

Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering.
Check out our other benefits at Block.

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