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 Square's Revenue leaders and own the most consequential decisions shaping how our go-to-market organization is structured, prioritized, and scaled across the full seller lifecycle — from acquisition and conversion through retention, expansion, and portfolio growth. You'll partner with senior leaders across Sales, Account Management, Partnerships, Finance, Data Science, Marketing, Product, and 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 motions need to evolve, and influence executive decisions through structured frameworks, operational 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 planning and investment strategy, the operating cadence of Revenue leadership, the design of Square's GTM motion across segmentation and coverage, and the executive narrative that aligns cross-functional partners around our most important bets. This role is designed to flex across the Revenue organization — anchored in Strategy & Ops with scope that can shift across acquisition and post-sale motions based on where the business most needs leverage. You will report to the Director of GTM Strategy & Operations and will mentor junior members of the team.

 

Key Responsibilities

GTM Strategy 

• Serve as a thought partner to senior Revenue leaders, helping shape business priorities, resource allocation, and performance strategy across the GTM organization.
• Partner with Revenue leadership and Finance to design the GTM motion — including segmentation, territory and coverage models, engagement strategies, and the operating playbooks that scale across acquisition and post-sale.
• Own complex, cross-functional strategic initiatives end-to-end: problem framing, business case, stakeholder alignment, execution, and post-launch measurement.

Performance & Business Insights

• Analyze pipeline, productivity, and lifecycle performance data to diagnose gaps and surface initiatives that improve conversion, deal velocity, retention, and expansion outcomes.
• Partner with Data Science and Finance to define KPIs, build executive-ready dashboards, and own the WBR/MBR cadence that keeps Revenue 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 the Revenue organization and its partner teams, 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 rep productivity across the full seller lifecycle — from prospecting and acquisition through portfolio management, retention, and expansion.
• Partner with CRM, Systems, and Engineering on the design of process, policy, and system architecture, including routing, SLAs, rules of engagement, segmentation, 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.

Qualifications

• 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 / Revenue Strategy & 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.