Manager, Field Sales

Apply RemoteChicago, IL, US Req ID: R0005093 Posted Date: 12/04/25 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

Square is building a world-class, high-accountability field sales organization — and we’re looking for a leader who is both a coach and a builder. You know the craft of selling deeply: how to open doors, generate pipeline, position value competitively, and close with precision. You lead from the front, developing your team through active engagement — not from the sidelines. You will be the driving force behind a disciplined, insight-led sales motion that blends in-person selling with proactive outbound strategy. Your leadership will elevate both the quality and velocity of revenue while shaping a culture rooted in excellence, ownership, and growth. If you are a hands-on leader with deep product expertise, strong competitive instincts, and a track record of raising the bar for sellers — this is your next move.

You will:

Lead with expertise in the field

• Develop Territory Account Executives through active, in-market coaching — from sourcing and opening conversations to consultative discovery, competitive positioning, and closing with clarity.
• Model world-class selling by joining prospect and customer meetings, demonstrating product fluency, value articulation, and decisive deal strategy.
• Spend significant time in the field with your team, strengthening local relationships, fueling community-driven pipeline creation, and ensuring sellers experience Square through a human, product-driven presence.

Operate in the details

• Manage pipeline and KPIs with rigor — diagnosing gaps, identifying risks, expanding coverage, and guiding AEs to create and progress high-quality opportunities.
• Run disciplined weekly pipeline , forecast ,and deal reviews that drive action , accountability ,and predictable outcomes across multiple markets.
• Use data-backed insights to coach AE effectiveness , elevate sales execution ,and ensure consistent momentum across high-velocity , complex sales cycles.

Build a high-performance , high-accountability culture

• Create an environment defined by trust , clear expectations , ownership ,and open communication .
• Hold the team to a high bar of execution while providing the clarity , structure ,and hands-on coaching needed to meet it .
• Hire , onboard ,and develop AEs to ramp quickly , deepen product expertise ,and consistently exceed quota.

Scale expertise , process ,and go-to-market effectiveness

• Become a product and competitive expert — ensuring your team can confidently articulate Square’s value and differentiation .
• Build scalable , repeatable field sales motions that increase funnel quality , improve outbound productivity,and accelerate growth in your assigned cities .
• Continuously refine strategy,p laybooks,and operating rhythms to deepen Square’s presenceand win market share across key local ecosystems.

Partner and innovate across the business

• Champion the customer voiceand collaborate cross-functionallyto strengthen product-market fitand unlock new revenue pathways .
• Engage deeply with community networks ,partners,and local events to amplify brand awarenessand fuel top-of-funnel opportunity creation.

You have:

• 8+ years of sales success , ideally in a high-growth environment
• 5+ years of leadership experience , preferably managing field account executives
• Experience in high-transaction SaaS or financial services sales
• Strong bias toward actionand experimentation , balanced with thoughtful decision-making
• A track record of buildinga winning , high-performing culture through hands-on leadershipand coaching
• Extensive experience operatingin a metrics-driven sales organization
• Proven abilityto influenceand collaboratewith cross-functional partnersin a rapidly scaling business
• Experience scalingand overseeing large Field Sales teams
• Strong abilityto communicateand build relationshipswith senior executives
• Excellent interpersonal , leadership , organizational ,and communication skills

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 ona cost of labor indexfor 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 modifiedin the future.To finda location's zone designation , please referto this resource.Ifa locationof interest is not listed , please speakwitha recruiterfor additional information. Zone A: ($198 ,000 - $297 ,000) Zone B: ($184 ,000 - $276 ,000) Zone C: ($174 ,000 - $261 ,000) Zone D: ($164 ,000 - 246 ,000) Amounts listed above include target variable compensation. We're workingto builda more inclusive economy where our customers have equal access to opportunity,and we striveto live by these same valuesin building our workplace.Block is an equal opportunity employer evaluating all employeesand job applicants without regardto identity or any legally protected class.We will consider qualified applicantswith arrest or conviction recordsfor employmentin accordancewith stateand local lawsand "fair chance" ordinances.We believein being fair,and are committedto an inclusive interview experience,includ ing providing reasonable accommodations to disabled applicants throughoutthe recruitment process.We encourage applicants to share any needed accommodationswith their recruiter , who will treat these requests as confidentially as possible. Wantto learn more about what we're doingto builda workplace that is fairandsquare? Check out our I+D page. Application Guidelines Candidates may submit up to 9 active applications withina 60-day period.Reapplications to thesame role are accepted 90 days aftera previous application has been reviewed. Use of AI in Our Hiring Process We may use automated AI tools toevaluate job applications for efficiencyand consistency.These tools complywith local regulations,includ ing bias audits,and we handle all personal datain accordancewith stateand local privacy laws.Contact us herewith hiring practice or data usage questions. Every benefitwe offeris designed with one goal: empowering you todo the best workof your career while buildingthe life you want.Remote work , medical insurance , flexible time off , retirement savings plans,and modern family planning are just someof our offering. Check out our other benefits at Block. Block , Inc.(NYSE: XYZ) builds technologyto increase access tothe global economy.Eachof our brands unlocks different aspects ofthe economy for more people. Square makes commerceand financial services accessible tosellers. *Cash App is theeasy wayto spend,s end,and store money.* Afterpay is transformingthe way customers manage their spending over time.* TIDAL isa music platformthat empowers artists tot hrive as entrepreneurs.* Bitkey isa simple self-custody wallet built for bitcoin.* Proto** isa suiteof bitcoin mining productsand services.Together,were helping builda financial systemthat is open toeveryone.*