Senior Manager, GTM Strategy

Block

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. The Role In 2026, Square is focused on deepening our presence in key verticals and the Sales Intelligence team will play a critical role in the success of this effort, acting as the translation layer between GTM teams and our partners on Product ensuring roadmaps unblock deals and accelerate existing account growth. In the Senior Manager role you will define and drive our Services vertical strategy, from identifying growth opportunities to influencing roadmap priorities and accelerating revenue performance, all closely tied to our sellers’ feedback and the deals our team are working. This is a highly autonomous, commercially oriented role with direct influence on product direction and go-to-market execution.

Requirements

8–12+ years of experience in sales strategy, product strategy, vertical GTM, consulting, or similar fields
Proven track record of leading global, cross-functional strategic initiatives that drive revenue growth, retention, and expansion
Strong commercial instincts and comfort tying business decisions to revenue outcomes
Demonstrated ability to partner with and influence senior executives and align diverse stakeholders around strategic priorities
Exceptional problem-solving and analytical skills; able to translate complex data into actionable insights and executive recommendations
Experience operating in ambiguity, driving clarity, and executing in a fast-paced, dynamic environment
Executive-ready communication and storytelling skills
A passion for helping customers grow and thrive with Square

Responsibilities

Drive Measurable Revenue Impact
Partner across Sales and Product leadership to improve win rates, expansion outcomes, and reduce churn through stronger product-market alignment
Translate roadmap priorities into actionable field guidance
Identify recurring deal blockers and convert insights into scalable solutions
Shape Product Roadmap Direction
Partner with Product leaders to prioritize Services vertical investments
Quantify the revenue impact of roadmap decisions
Advocate for innovation that drives durable differentiation
Create tight feedback loops between GTM insights and product execution
Lead Cross-Functional Alignment
Build strong partnerships across Sales, Product, and cross-functional teams
Institutionalize mechanisms for signal clarity and insight synthesis
Elevate strategic tradeoffs to leadership with data-backed recommendations