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.

 

Block takes a market-based approach to pay, and pay may vary depending on your location. U.S. locations are categorized into one of four zones based on a cost of labor index for that geographic area. The successful candidate’s starting pay will be determined based on job-related skills, experience, qualifications, work location, and market conditions. These ranges may be modified in the future.

To find a location’s zone designation, please refer to this resource. If a location of interest is not listed, please speak with a recruiter for additional information. 

 

Zone A:$179,704—$269,557 USDZone B: $167,104—$250,656 USDZone C:$158,179—$237,231 USDZone D:$152,779—$229,131 USDApplication Guidelines

Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed.

Use of AI in Our Hiring Process

We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws. 

Contact us here with hiring practice or data usage questions.

Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern