• Lead full sales cycles - from discovery to signed contract • Own relationships with CFOs and Controllers, deeply understanding their workflows and pain points • Demonstrate how DualEntry delivers clarity, automation, and 10× efficiency to their accounting operations • Refine messaging, build talk tracks, test hypotheses, battlecards and shape how we sell • Collaborate closely with founders, GTM, product, and marketing teams • Serve as the bridge between customers and product - influencing roadmap and positioning • Help scale our sales motion with speed, precision, and high accountability

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 looking for a Territory Account Executive to join our newly established field sales organization. Our goal is to bring a local experience to our Sellers (aka customers/merchants) everywhere. You will engage with our Sellers in a relevant and authentic way, demonstrate Square's mission of economic empowerment and provide a truly local presence. This individual contributor sales role will work with restaurants, retailers and service based businesses in our largest and highest potential markets. THIS IS A HUNTER AND FIELD BASED SALES ROLE. You will build a vision and strategy plan for winning market share in your city. You will collaborate to create a build top of funnel leads, referrals, connect with local partners, attend/host local events within your community to generate new business, kickstarting the flywheel and build Square's brand awareness within your city. This role requires excellent communication skills, persistence, and a strong ability to build rapport with sellers to negotiate and close complex deals both remotely and in person. You Will - Sell into your market in-person. You will sell face to face 80% of the time to source leads, perform discovery and demos to generate interest and close deals selling our Square ecosystem - Get to know the active Square Sellers within your community - keep a pulse on their account health and partner with account management and customer support, and generate referrals - Engage and partner with onboarding teams to ensure Sellers are implemented successfully - Build a sustainable, top of funnel pipeline through a combination of tactics - walking your city and performing 50-60 drop-ins a week to prospective sellers, create a referral channel with active Square sellers, strategic partnerships or local community associations - Develop a strong on-hands skill of demo and onboarding of Square hardware and software solutions - Work with our channel sales team to identify complementary partners in your market for referrals and build that referral channel - Cultivate a deep understanding of the business and technology needs of our primary vertical markets (restaurants, retail and services) - Achieve and exceed monthly sales goals and key performance indicators (KPIs) - we are big on metrics - Utilize Salesforce to track, monitor, and report on sales activities, pipeline status, and outcomes You Have - 2+ years of sales experience in a full cycle closing role with direct 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 or near 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) Pay Transparency 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 on a cost of labor index for 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 modified in the future. To find a location's zone designation, please refer to this resource . If a location of interest is not listed, please speak with a recruiter for additional information. Zone A: ($148,700 - $223,100) Zone B: ($138,300 - $207,500) Zone C: ($130,900 - $196,300) Zone D: ($123,400 - $185,200) Amounts listed above include target variable compensation. 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 an equal opportunity employer evaluating all employees and job applicants without regard to identity or any legally protected class. We will consider qualified applicants with arrest or conviction records for employment in accordance with state and local laws and "fair chance" ordinances. 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 a workplace that is fair and square? Check out our I+D page . While there is no specific deadline to apply for this role, U.S. roles are typically open for an average of 55 days before being filled by a successful candidate. Please refer to the date listed at the top of this job page for when this role was first posted. Application Guidelines Candidates may submit up to 9 active applications within a 60-day period. Reapplications to the same role are accepted 90 days after a previous application has been reviewed. Use of AI in Our Hiring Process We may use automated AI tools to evaluate job applications for efficiency and consistency. These tools comply with local regulations, including bias audits, and we handle all personal data in accordance with state and local privacy laws. Contact us here with hiring practice or data usage questions. Every benefit we offer is designed with one goal: empowering you to do the best work of your career while building the life you want. Remote work, medical insurance, flexible time off, retirement savings plans, and modern family planning are just some of our offering. Check out our other benefits at Block. Block, Inc. (NYSE: XYZ) builds technology to increase access to the global economy. Each of our brands unlocks different aspects of the economy for more people. Square makes commerce and financial services accessible to sellers. Cash App is the easy way to spend, send, and store money. Afterpay is transforming the way customers manage their spending over time. TIDAL is a music platform that empowers artists to thrive as entrepreneurs. Bitkey is a simple self-custody wallet built for bitcoin. Proto is a suite of bitcoin mining products and services. Together, we're helping build a financial system that is open to everyone.

• Drive new business revenue across the Northeast region • Build and execute a regional sales strategy • Prospect into enterprise accounts and develop qualified pipeline • Identify business pains related to productivity and technology issues • Engage stakeholders across various domains • Evangelize Nexthink’s value proposition • Lead discovery and business case development • Manage customer expectations and relationships • Consistently exceed sales targets

About Gusto At Gusto, we're on a mission to grow the small business economy. We handle the hard stuff — payroll, health insurance, 401(k)s, and HR — so owners can focus on their craft and their customers. With teams in Denver, San Francisco, and New York, we support more than 500,000 small businesses nationwide and are building a workplace that reflects the people we serve. All full-time employees receive competitive base pay, benefits, and equity (RSUs) — because everyone who helps build Gusto should share in its success. Offer amounts are determined by role, level, and location. Learn more about our Total Rewards philosophy. AI is a fundamental part of how work gets done at Gusto. We expect all team members to actively engage with AI tools relevant to their role and grow their fluency as the technology evolves. AI experience requirements vary by role and will be assessed during the interview process. About the Role: Gusto is building its PEO sales org from the ground up, and we're looking for a quota-carrying seller to be one of the founding members of that team. This is a true ground-floor opportunity: you'll be among the first reps closing PEO business at Gusto, working directly with the Head of PEO Sales to prove out and scale the motion. You'll drive new PEO revenue by selling Gusto's co-employment solution to both net-new prospects and our existing base of 400,000+ customers — Gusto's single biggest competitive advantage over legacy PEOs. The market opportunity is real, the pace is fast, and the early sellers on this team will help define what "good" looks like.Use AI-powered workflows as a core part of how you sell: running assigned tools daily, surfacing friction and inefficiencies as you find them, and collaborating with your team to influence what gets built or improved next. If you're excited to roll up your sleeves, lead by example, and architect something from scratch, let's talk. About the Team: You'll be an early individual contributor on Gusto's founding PEO sales team, reporting to the Head of PEO Sales. As one of the first sellers, you'll carry a personal book of business, run the full sales cycle end to end, and serve as a Subject Matter Expert who guides prospects through complex co-employment buying decisions. You'll partner closely with HR, benefits, and payroll counterparts to deliver a seamless customer experience, and you'll work alongside the Head of PEO to surface what's working in the field — feedback that directly shapes the playbook, tooling, and pipeline architecture as the org scales. Your biggest unfair advantage: Gusto's existing install base. Like the best scaled PEOs, a meaningful share of your pipeline will come from converting existing payroll customers to PEO — and you'll be one of the first to run that motion at scale. Here’s what you’ll do day-to-day: - Own the full sales cycle. Prospect, qualify, run discovery, demo, navigate complex buying groups, and close. This is a quota-carrying role for a seller who's comfortable owning a deal from first touch to signed agreement. - Sell across both motions. Close net-new prospects and convert existing Gusto payroll customers to PEO. You'll learn the distinct objections, value propositions, and rhythms of in-base selling vs. cold-start prospecting. - Serve as a PEO Subject Matter Expert. Guide prospects through co-employment, benefits, compliance, and the practical realities of moving onto a PEO. Build and maintain deep knowledge of PEO compliance, co-employment regulations, and applicable state and federal employment law. - Sell with selling-season fluency. Understand and plan around PEO's concentrated selling window (Sept–Dec, with the bulk of new business landing Jan 1). Build pipeline early and manage your funnel to hit those timelines. - Work the channel. Partner with broker, GA, and accountant referral sources to develop pipeline, and feed insights back on what's converting. - Manage your pipeline rigorously. Keep Salesforce clean and current, forecast accurately, and operate within the sales stages, routing, and reporting the team establishes. - Use AI to sell smarter. Bring genuine AI fluency to your daily workflow — leveraging AI tools for prospecting, call prep, follow-up, and forecast hygiene. We expect our sellers to be hands-on with AI and to share what's working with the broader team. - Collaborate cross-functionally. Work closely with Marketing, Product, and the broader Sales org to surface market signals, sharpen positioning, and improve the customer experience. Here’s what we're looking for: - PEO / HCM Sales Experience: 4+ years in a closing sales role, ideally in PEO, HCM, or benefits. Direct PEO selling experience is strongly preferred. - Quota Attainment: Consistent, demonstrable track record of meeting and exceeding individual sales targets. - Full-Cycle Ownership: Proven ability to own a deal end to end — prospecting, discovery, multi-stakeholder navigation, and close — in a consultative, complex sale. - Selling-Season Fluency: Familiarity with PEO's Jan 1 selling cycle (Sept–Dec pipeline build, renewal dynamics) is a strong plus and a key screen for PEO-specific experience vs. generic HCM. - Install-Base Conversion: Experience selling into or converting an existing customer base to a higher-tier or adjacent product is a plus. - Channel Familiarity: Understanding of broker, GA, and accountant referral channels in the PEO or benefits space. - Sales Acumen: Strong working knowledge of inbound and outbound sales methodologies in SMB SaaS or HCM/PEO environments. - Collaboration: Ability to work effectively across HR, Benefits, Product, and Marketing; excellent interpersonal skills. - AI Fluency: Proven, day-to-day experience integrating AI into how you work — across writing, research, prep, and summarization as a core part of your workflow, with a track record of giving clear, useful feedback that helps improve your tools and processes. - Technical Proficiency: Salesforce.com (SFDC) experience required; familiarity with HCM platforms and benefits administration tools preferred. Our cash compensation amount for this role is $115,000 to $129,500 USD for Denver, Phoenix, Atlanta, Chicago metro areas and $140,000 to $150,000 USD for San Francisco & New York. This OTE is structured with a target 60% base pay and 40% commission pay with an uncapped commission structure. Final offer amounts and the exact base/commission split are determined by multiple factors including candidate location, experience, and expertise and may vary from the amounts listed above. Gusto has physical office spaces in Denver, San Francisco, and New York City. Employees who are based in those locations will be expected to work from the office on designated days approximately 2-3 days per week (or more depending on role). The same office expectations apply to all Symmetry roles, Gusto's subsidiary, whose physical office is in Scottsdale. Note: The San Francisco office expectations encompass both the San Francisco and San Jose metro areas. When approved to work from a location other than a Gusto office, a secure, reliable, and consistent internet connection is required. This includes non-office days for hybrid employees. Our customers come from all walks of life and so do we. We hire great people from a wide variety of backgrounds, not just because it's the right thing to do, but because it makes our company stronger. If you share our values and our enthusiasm for small businesses, you will find a home at Gusto. Gusto is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex (including pregnancy, childbirth, or related medical conditions), marital status, ancestry, physical or mental disability, genetic information, veteran status, gender identity or expression, sexual orientation, or other applicable legally protected characteristic. Gusto considers qualified applicants with criminal histories, consistent with applicable federal, state and local law. Gusto is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans in our job application procedures. We want to see our candidates perform to the best of their ability. If you require a medical or religious accommodation at any time throughout your candidate journey, please fill out this form and a member of our team will get in touch with you. Gusto takes security and protection of your personal information very seriously. Please review our Fraudulent Activity Disclaimer. Personal information collected and processed as part of your Gusto application will be subject to Gusto's Applicant Privacy Notice.