Executive Operations Strategist Jobs in Santa Rosa, CA

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.

As the Manager, GTM Strategy & Operations, you'll play a central role in how Square's global Sales organization plans, prioritizes, and executes. You'll pair strategic depth with operational rigor to turn business priorities into results.

This is a builder's role at the intersection of GTM strategy, revenue operations, and cross-functional execution. You'll own complex, multi-stakeholder workstreams end-to-end, from problem framing through analysis, alignment, and shipped outcomes. You'll serve as a trusted voice in Sales planning, bringing an independent point of view on where our GTM motion needs to evolve.

You'll partner closely with Sales, Finance, Analytics, and Product/Engineering to design the operating cadence, analytical frameworks, and system architecture behind Square's Sales motions. Success is a more efficient operating rhythm, sharper funnel diagnostics, and strategy that translates cleanly into on-the-ground action.

This role requires a strong combination of strategic thinking, operational excellence, and executive influence. You will report to the Director of GTM Strategy & Operations, Global Sales.

• Sales GTM Strategy & Planning:

  • 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.
  • Size opportunities and build data-driven investment cases that inform capacity planning, incentive design, and where Square directs Sales resources.

  Performance & Productivity 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, stand up dashboards, and operate the WBR/MBR cadence that keeps Sales leadership close to the business.
  • Translate complex analyses into rigorous performance narratives and actionable recommendations that inform leadership decisions.

  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.

• 5+ years of experience in strategy and operations, revenue/sales operations, GTM strategy, business operations, or management consulting, ideally within SaaS, FinTech, or high-growth technology.
• A track record of owning complex, cross-functional strategic initiatives end-to-end - from problem framing through analysis, stakeholder alignment, execution, and measurement.
• Strong commercial instincts and comfort tying operational decisions to revenue outcomes, funnel health, and rep productivity.
• 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.
• Excellent communication and stakeholder skills: you can influence senior partners without direct authority and keep cross-functional teams aligned through ambiguity.
• Hands-on experience with CRM, BI, and data warehouse tools (e.g., Salesforce, Looker, Snowflake, or equivalents) - able to pull data, translate it into insights, and make it useful for Sales leaders.

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