• Exhibit effective appointment setting skills and set the required number of appointments each week with the correct decision makers. • Effective Selling Skills: Utilizing professional selling skills, discover prospects incremental and programmatic needs, effectively communicates Staples value propositions, capabilities, products and assortments including all categories. Capable of overcoming objections and closing the sale. • Utilize prescribed selling tools to prioritize activities and drive efficiency, as well as to document customer engagement and information (ex: Priority List, Tenfold, SFDC). • Internal Partnerships: Effectively work with customer support/set up teams and category specialists to progress deals forward to closed won. • Implements and ramps wins driving compliance to new account/program.. • Expertise of prospect industry buying process’ and ability to support product selection and standardization.

• Align with the company's strategic objectives • Handle and grow revenue and market share at designated Enterprise accounts • Develop and deliver business plans to address customer priorities • Convey public intelligence about customer technology footprints and competitive landscape • Introduce domain product and service experts while maintaining account oversight • Own account relationships and drive overall customer success • Build consensus and develop relationships at multiple levels • Lead large scale transactions to close deals • Build pipeline, forecast business, lead the internal team

Role Description As an Enterprise Account Executive, you'll be the tip of the spear for Square's most strategic, high-value deals. You'll navigate multi-threaded sales cycles with executive stakeholders involving technical integrations and cross-functional alignment. This is a role for a seasoned enterprise seller who owns the full deal lifecycle — from cold outreach to signed contract — and thrives in the complexity that comes with it. You'll join a high-performing enterprise sales team that is deeply supported and strategically prioritized. Square is making significant investments to bring Square upmarket at scale and enable enterprise sales success. This is a team that operates with rigor, moves with urgency, and takes pride in signing the largest deals for the company. You Will - Craft and Lead Deal Strategy: Develop sophisticated, insight-led sales narratives tailored to client business priorities. Identify the right entry points, mapping stakeholder influence, and building compelling business cases that create clear ROI. - Own the Full Sales Cycle: Manage your pipeline end-to-end with precision — from prospecting and discovery through negotiation and close — qualifying rigorously and driving momentum at every stage without losing sight of the details. - Lead Technical, Complex Sales Cycles: Partner closely with Solutions Engineering to scope platform requirements and API integrations. Translate deeply technical concepts into language that resonates with executive decision-makers and know when to bring in the right expert at the right moment. - Orchestrate Internal Alignment: Quarterback cross-functional stakeholders across Finance, Legal, Risk, Product, Solutions Engineering, and Account Management — proactively surfacing blockers, resolving ambiguity, and ensuring everyone is aligned and moving in the same direction. - Represent Square at the Highest Level: Represent Square in C-suite meetings, on stage at industry conferences, or in working sessions with a prospect's technical team — with executive presence that is polished, credible, and authentic. - Build Block's Enterprise Network: Represent Square at industry events, trade shows, and networking functions; develop lasting relationships with senior leaders at leading brands and platform partners. - Be a Multiplier for the Business: Channel the voice of the customer internally to influence product roadmaps and go-to-market strategy; apply AI tools to sharpen your research, automate workflows, and increase your overall output. Qualifications - 8+ years of enterprise sales experience, with a track record of closing complex, high-value deals with end-to-end ownership. - Deep experience in technical sales cycles — fluent in conversations involving API integrations, custom development, and platform configuration, and collaborate naturally with Solutions Engineering teams. - A proven ability to orchestrate multi-stakeholder deals — internally and externally — with exceptional communication, follow-through, and organizational discipline. - Executive presence that's equally at home on a conference stage, in a C-suite boardroom, or on a discovery call with a technical champion. - Experience selling a complex ecosystem of SaaS or fintech products, ideally in payments, commerce, or adjacent verticals. - The ability to operate independently in a fast-paced, ambiguous environment — you don't wait to be told what to do next. - A talent for translating complexity into clarity — whether that's simplifying a technical integration for a CFO or structuring an ambiguous problem for an internal stakeholder. - A BA/BS degree or equivalent professional experience. - Willingness to travel ~40%. Benefits - Remote work. - Medical insurance. - Flexible time off. - Retirement savings plans. - Modern family planning. Company Description 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: The easy way to spend, send, and store money. - Afterpay: Transforming the way customers manage their spending over time. - TIDAL: A music platform that empowers artists to thrive as entrepreneurs. - Bitkey: A simple self-custody wallet built for bitcoin. - Proto: A suite of bitcoin mining products and services.

• Ramp quickly on Medely’s platform, value proposition, and the healthcare staffing landscape. • Begin 1:1s with your manager, align on your 30-60-90 plan, and shadow discovery and demo calls. Learn the sales tech stack (Salesforce, Outreach, Gong, Google Workspace) and territory structure. • Start building your outbound prospect list and following up on inbound leads. • Own a territory plan for outpatient healthcare facilities in your assigned region. • Run consultative discovery calls that uncover operational pain points and staffing needs. • Demonstrate Medely’s platform with confidence, tailoring use cases to each facility type. • Generate pipeline primarily through self-prospecting; while some inbound opportunities will come your way, the majority of your success will come from your own outreach and relationship-building. • Begin closing your first deals. • Consistently meet or exceed activity metrics and pipeline targets. Navigate multi-stakeholder sales cycles, engaging both clinical and administrative decision-makers. • Build a steady stream of net new opportunities while also expanding relationships with existing customers. Partner with Customer Success to ensure smooth onboarding and high adoption. • Be a top-performing AE, exceeding quota and contributing to Medely’s growth in your market. • Share market insights with leadership to refine our go-to-market approach. • Mentor newer AEs as they ramp.