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:

As the Senior Manager, GTM Strategy & Operations, you'll be a strategic partner to senior Sales leadership and own the most consequential decisions shaping how Square's go-to-market organization is structured, prioritized, and scaled. You'll partner with senior leaders across GTM, Finance, Analytics, and Product/Engineering to translate company priorities into clear GTM direction and shape the bets that define Square's revenue trajectory.

This is a hands-on strategic role. You'll define the right questions, bring an independent point of view on where our GTM motion needs to evolve, and influence executive decisions through structured frameworks, financial rigor, and sharp written narrative. You'll also stay close to execution — building prototypes, owning complex cross-functional workstreams end-to-end, and raising the analytical bar across the team.

Your work will shape annual planning and investment strategy, the operating cadence of Sales leadership, the long-range design of Square's GTM motion across segmentation and coverage, and the executive narrative that aligns cross-functional partners around our most important bets. You will report to the Director of GTM Strategy & Operations, Global Sales, and will mentor junior members of the team.

You Will:

Sales GTM Strategy & Planning

• Serve as a thought partner to senior Sales and GTM executives, helping shape business priorities, resource allocation, and performance strategy.
• Partner with Sales leadership and Finance to shape the GTM strategy for the Sales organization, including segmentation, territory design, coverage models, and rep engagement frameworks.
• Own complex, cross-functional strategic initiatives end-to-end: problem framing, business case, stakeholder alignment, execution, and post-launch measurement.

Performance & Business Insights

• Analyze Sales funnel data to diagnose performance gaps and surface initiatives that improve contact-to-close rates, deal velocity, and quota attainment.
• Partner with Analytics and Finance to define KPIs, build executive-ready dashboards, and own the WBR/MBR cadence that keeps Sales leadership close to the business.
• Translate complex analyses into executive-ready performance narratives and recommendations that drive leadership decisions and shape strategic bets.

Cross-Functional Execution & Program Management

• Lead cross-functional workstreams across Sales, Marketing, Product, Engineering, Analytics, and Finance, driving clarity, alignment, and structure through ambiguity.
• Translate business goals into clear technical requirements (PRDs/BRDs) and partner with technical teams to deliver programs on time and to spec.
• Break large, multi-quarter initiatives into pilots and iterations; manage the roadmap in collaboration with leadership and cross-functional partners.

AI, Automation & Process Innovation

• Identify and champion AI-native opportunities to increase Sales productivity across prospecting, lead scoring, deal support, and rep workflow automation.
• Partner with CRM, Systems, and Engineering on the design of process, policy, and system architecture, including routing, SLAs, rules of engagement, and handoffs.
• Stay at the frontier of AI-native GTM tooling and bring proven new approaches into the team's playbook.
• Raise the AI-native operating bar across the GTM Strategy & Ops team — model what hands-on AI fluency looks like for other operators.

Team Leadership & Craft

• Mentor junior members of the GTM Strategy & Ops team; raise the bar on analytical rigor, written communication, and executive-ready output.
• Model the operating standards (ownership, bias to action, builder mindset) that define how the team works.

You Have:

• 8+ years of related experience with a Bachelor's degree; or 6 years and a Master's degree; or a PhD with 3 years experience; or equivalent experience in GTM Strategy, Sales Strategy, Revenue Operations, Business Operations, or Management Consulting — ideally within SaaS, FinTech, or high-growth technology.
• Proven track record of leading global, cross-functional strategic initiatives that drive measurable revenue, retention, or expansion outcomes.
• Demonstrated ability to influence executive-level stakeholders through structured analysis, clear narratives, and strong business judgment.
• Strong commercial instincts; comfort tying strategic decisions to investment prioritization and revenue outcomes.
• AI-native operating mindset: fluent with AI/LLMs in day-to-day work, hands-on with workflow automation, and energized by shipping real tools that remove manual work from the team.
• Expertise in CRM systems (e.g., Salesforce), GTM analytics tools (Looker, Snowflake, or equivalents), and SQL for independent data analysis.
• Executive-ready written and verbal communication — able to distill complex analyses into clear leadership narratives and board-level recommendations.
• Comfort with ambiguity and a low-ego, ownership mindset — no task is too small, and you're motivated to build the operating system behind a world-class Sales organization.

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

 

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:$156,200—$234,200 USDZone B: $145,200—$217,800 USDZone C:$137,400—$206,200 USDZone D:$129,600—$194,400 USD

Application 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 family planning are just some of our offering. Check out our other benefits at Block.

Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we’re helping build a financial system that is open to everyone.

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