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 best-in-class, high-impact field sales organization, and we are looking for an exceptional Territory Account Executive — someone who consistently exceeds expectations, takes full ownership of their territory, and brings Square’s mission of economic empowerment directly to the businesses that need it most.

This is a field-driven, execution-focused role designed for individuals who thrive in dynamic, demanding environments. You will spend most of your week out in the market — meeting businesses, conducting live demos, and closing deals with confidence. The pace is fast, the expectations are high, and your ability to operate strategically and decisively will determine your success.

You will serve as Square’s presence and competitive advantage in one of our highest-opportunity markets — responsible for building pipeline from the ground up, elevating Square’s visibility in your community, establishing high-value partnerships, and helping local businesses grow through our ecosystem of industry-leading software and hardware.

If you are motivated by impactful work, driven to outperform, and eager to join a high-performance team with high standards, this role is built for you.

You will:

Lead your market with disciplined, in-person execution

• Spend ~80% of your week in the field — walking your territory, engaging local businesses, and driving 50–60 targeted business visits each week.
• Run a full-cycle, self-sourced sales motion: generate leads, identify needs, deliver compelling demos, and close deals across Square’s full product suite.

Establish yourself as the go-to Square expert in your city

• Build strong, trust-based relationships with local sellers by being present, reliable, and value-driven.
• Partner cross-functionally to ensure a seamless onboarding experience and fast time-to-value for new sellers.
• Implement a disciplined referral strategy to turn every new customer into future opportunities.

Build a high-velocity pipeline from the ground up

• Develop a repeatable top-of-funnel engine through door-to-door outreach, community engagement, events, networking, and targeted partnerships.
• Work with channel partners to generate a consistent, high-quality referral stream that grows over time.

Master your verticals and sell with precision

• Build deep expertise in key verticals — including restaurants, retail, and services — to diagnose challenges and position the right Square solutions.
• Sell consultatively and competitively, staying proactive and strategic throughout the sales cycle.

Achieve exceptional results in a high-accountability environment

• Maintain strong operational rigor in Salesforce: track activity, manage pipeline, and forecast accurately.
• Measure performance frequently and improve continuously.
• Consistently exceed quota within a culture where high standards are the norm.

You have:

• 3+ years of sales experience in a full cycle closing role with field sales experience
• Experience exceeding sales targets, selling a diverse ecosystem of products, and closing complex deals
• Ability to drive deals independently in a fast-paced, dynamic environment 
• Business development experience (e.g. hunting and cold calling)
• Since this is a field position, you must have reliable transportation and live in the market you are serving
• A collaborative and team player mentality
• Prior Salesforce experience or equivalent
• Even better:
• 2+ years of payment processing OR related technology (i.e. payroll, loyalty, time management)
• 1+ years of relevant audience experience (experience working in/selling to restaurants, retailers or services based businesses)

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

Location: Remote (US only) + 60–80% travel to jobsites nationwide

About Human Agency

We're scaling rapidly and have a growing pipeline of opportunities that demand exceptional talent across disciplines. Our mission is to bring on individuals, from creative producers to technical experts to entrepreneurial leaders, who can help us realize this next chapter of growth.

We are a company of doers. Leaders roll up their sleeves, teams work flat, and everyone contributes to what ships. Titles don't insulate us from feedback or basics. We invite critique, learn quickly, and keep raising the bar. The best ideas win here, no matter where they come from, because clients trust us to deliver the strongest outcomes every time.

Our clients' missions, products, and bottom lines are sacred. We immerse ourselves in their world, becoming stewards of their goals and partners in solving big problems. Every product, strategy, or asset we create must be both beautiful and functional; practical, usable, and designed for real-world impact.

Humans are our most valuable resource, and we only grow by hiring people who push us forward. Across strategy, engineering, design, data, and operations, we seek out teammates who raise the bar and make us better. Always hire up, never down.

We partner with organizations of all sizes to explore, design, and implement AI strategies that are secure, scalable, and human-centered. We believe AI should amplify human potential, not replace it and we build with that conviction in every engagement. From advisory and tooling to implementation and education, we meet clients where they are at and help them integrate AI in ways that align with their mission and values. Our goal is to empower teams to work smarter, move faster, and unlock new possibilities through thoughtful, responsible innovation.

And through it all, we lead with purpose, love, and adventure. We do meaningful work with people we care about, and we make the ride an adventure worth taking. Because at Human Agency, who we are and how we work are one and the same.

The Opportunity

We partner with large design-build companies (~$10B revenue) that employ thousands of project engineers and project managers running complex jobsites across the country. Human Agency is building custom AI tools and strategies to make those teams dramatically more effective. The missing piece is someone who lives in the field, understands how construction actually works, and can connect the dots between emerging technology and real jobsite needs.

That’s this role. You’ll travel to active jobsites, shadow project teams, and develop a deep, current picture of how work gets done, where it breaks down, and where technology can genuinely help. You’ll be the person who’s wildly up to speed on everything happening in construction technology — from autonomous equipment to AI-assisted estimating to reality capture — and can evaluate where each piece might actually fit in the real workflows you’re observing.

You carry two mandates. Enablement: helping field teams understand and leverage AI tools to work better, faster, and smarter. Intelligence: capturing expert knowledge from the people who actually build things, understanding the technology landscape with depth and nuance, and feeding those insights directly into Human Agency’s venture studio and product roadmap. Your perspective shapes what we build, who we invest in, and how we think about making our design-build partners great.

What You’ll Own

Field Intelligence & Expert Knowledge Capture

• Conduct structured job shadows of Project Engineers, Project Managers, and superintendents across project types — healthcare, industrial, data centers, commercial — to map how work actually flows day-to-day and where the friction, waste, and brilliance live.
• Extract and codify expert knowledge from experienced construction professionals. The people you shadow know things that aren’t written down anywhere. Your job is to capture that institutional intelligence and make it an asset.
• Synthesize field observations into actionable briefs for Human Agency’s venture studio and product teams, directly informing what to build, what to invest in, and where the biggest opportunities are.
• Build and maintain a living knowledge base of construction workflows, pain points, and technology gaps across our design-build partners’ project portfolios.
• Identify systemic patterns across jobsites and project types that point to high-leverage opportunities for technology intervention or process improvement.

Contech Landscape & Evaluation

• Maintain comprehensive, current knowledge of the construction technology landscape. You should have an informed opinion on every major platform, startup, and emerging capability in the space.
• Evaluate emerging technologies like Bedrock Robotics (autonomous heavy equipment), reality capture tools, AI co-pilots for estimating and scheduling, and next-generation project management platforms against real jobsite needs you’re observing firsthand.
• Develop technology fit assessments: given what you see in the field, where could a given tool actually create value vs. where would it be shelfware? Your judgment on this is the product.
• Brief Human Agency and client leadership on contech trends, investment-worthy companies, and technology bets with a practitioner’s perspective, not a vendor’s pitch.
• Contribute directly to Human Agency’s venture studio thesis on where the AEC industry is heading and which technology gaps represent real opportunities.

AI Enablement & Coaching

• Help jobsite teams understand and adopt AI-assisted workflows that Human Agency has built for the client — tools for submittals, change orders, RFP assessment, meeting synthesis, quality knowledge, and more.
• Run hands-on coaching sessions (1:1, small group, lunch-and-learns) that translate AI capabilities into construction language. You’re teaching a PM how this saves them an hour on submittals, not lecturing about large language models.
• Identify the highest-leverage AI use cases for specific roles and project types based on what you’re seeing in the field, and work with our product team to customize solutions accordingly.
• Serve as the credible, trusted voice on AI and technology for field teams. You earn this by understanding their work, not by evangelizing from a slide deck.
• Surface adoption barriers, user friction, and workflow mismatches back to the product team so tools get better with every jobsite visit.

Who You Are

Required

• Construction industry experience (3+ years) with time spent on or around jobsites. You know what a three-week lookahead is, you’ve seen a PE’s actual day, and you understand the difference between how construction is supposed to work and how it actually works. Backgrounds in project engineering, project management, field operations, or construction technology.
• Deep fluency with the contech landscape. You follow the space obsessively — you know the players, the platforms, the funding rounds, and the gaps. You have a point of view on where it’s all heading.
• AI literacy that goes beyond using ChatGPT. You’ve built workflows, automated processes, and can demonstrate how AI tools change the way people work. You can teach this to others.
• Exceptional communication skills across audiences — you can have a credible conversation with a superintendent on a slab at 6am and brief a C-suite on technology strategy at 2pm.
• Comfort with heavy travel (60–80%) to jobsites across the country. This role lives in the field, not behind a desk.
• Natural credibility with construction professionals. You’re respected in those rooms because you understand the work, not just the tools.

Preferred

• Direct experience with construction technology platforms (Procore, PMWeb, OpenSpace, Bluebeam, BIM tools, or similar) — either as a power user, implementer, or builder.
• Background in construction technology or AEC innovation — whether at a startup, a GC’s operations or innovation team, or a technology consultancy serving the industry.
• Experience in technology evaluation, venture analysis, or strategic advisory roles where your judgment on “will this actually work” was the deliverable.
• Familiarity with how AI products are built — understanding how field insights and user research translate into product decisions.
• Comfort operating in a consulting structure where you’re a Human Agency team member embedded in a client’s organization and culture.

Why This Role Matters

Construction is a $13 trillion global industry where the people doing the work are brilliant but chronically underserved by their tools. Technology companies build for construction from the outside. Consultants advise from conference rooms. Nobody is living on jobsites, capturing what experts actually know, staying current on every emerging technology, and connecting those two things together.

That’s the gap this role fills. Your field intelligence shapes what Human Agency builds, who we invest in, and how we help our design-build partners operate at the highest level. Your enablement work ensures that the tools we’ve already built actually land with the people who need them. You’re the connective tissue between technology and the real world — and in an industry this large and this underserved, that’s a position with enormous leverage.

Equal Opportunity Commitment

Human Agency is an Equal Opportunity Employer. We value diverse backgrounds and strive to build an inclusive culture where everyone feels welcomed and empowered.