datascalehr Inc. Enterprise Account Executive New York, NY · Full time Company website

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datascalehr is building a new category: the AI-native context layer for global HCM. We sit between every system of record (Workday, SAP, Oracle) and every payroll provider, agent, and application that needs cross-system, cross-country workforce data. The results are staggering: what used to take six months of manual integration takes days and monthly payroll operations are 10x more efficient. The thesis is no longer theoretical. Three of the top five global payroll providers already run on datascalehr. KMod™, our proprietary knowledge engine, has processed 2M+ validated mappings across 1,100+ live connectors in 150+ countries. Foundation Capital, Gartner, and Microsoft all describe a "context layer" as the missing infrastructure for agentic AI. datascalehr has already built it for the hardest data domain in the enterprise. We are backed by Acadian Ventures, the leading early-stage venture firm investing in the new architecture of work. The people who do their best work at datascalehr build rather than maintain. They prefer writing the playbook over executing one that someone else wrote. They want to own outcomes, not just contribute to them. They are pragmatic about ambiguity and impatient to resolve it. If that sounds like you, we should talk.

Your Mission

This is a founding Enterprise Account Executive role at datascalehr. You report directly to the CEO and co-founder.  You are the first sales hire, and you own the entire enterprise direct motion from the ground up.  You will be selling into CHROs, CIOs, COOs, and CFOs at Global Fortune 2000 companies, navigating complex multi-stakeholder cycles and defining how datascalehr wins in the enterprise direct market.

A majority of our revenue today comes from global payroll service providers, not direct enterprise customers. The direct enterprise motion is the next phase, and that is the gap you fill. We are already in active contracts and POCs with our first direct enterprise customers, including Global Fortune 2000 companies.

You are not starting cold. You have a top-rated GTM engineering agency and a modern sales and marketing technology stack (Claude, HubSpot, Clay, HeyReach, and others) at your service. Your job is to develop and iterate the playbook that turns activity into repeatable new customer wins, and put datascalehr on a doubling growth trajectory within twelve months. Once the playbook works, you build the team that runs it.

You will also work alongside the Chief Customer Officer, who manages partner relationships, client success, and account expansion.

What You'll Do

• Own enterprise pipeline from qualification through close, with disciplined deal reviews and accurate forecasting.
• Drive new business across Global Fortune 2000 accounts, navigating complex multi-stakeholder cycles spanning CHROs, CIOs, COOs, CFOs, procurement, legal, and IT security.
• Build the enterprise sales playbook from scratch, including ICP, buying triggers, qualification criteria, demo flow, proposal structure, and close process.
• Partner directly with the CEO, CFO and CCO to refine positioning, pricing, packaging, and competitive intelligence as the motion takes shape.
• Bring a consultative, change-management approach to selling a category-defining product that requires educating the market.
• Hire and lead the team that runs the playbook once it is repeatable.

Who You Are

• 5-10 years of B2B SaaS or enterprise software sales experience with a strong individual closing track record.
• Proven ability to close six-figure and seven-figure enterprise deals.
• Comfortable selling into complex buying committees spanning HR, IT, Finance, Operations, Procurement, Legal, and C-suite.
• Built (not just executed) an enterprise sales motion at an early-stage or high-growth startup, with quantifiable pipeline you generated from near-zero.
• Founder mindset, energized by selling a category-defining product that requires educating the market. You build process, collateral, and competitive intelligence because that is what the moment requires.
• Technically fluent enough to hold your own with a CIO or CTO on data infrastructure, APIs, and AI.
• Execution-first. Rigorous on pipeline, sharp on discovery, relentless on follow-through.

Bonus

• HR tech, payroll, or workforce management domain experience.
• Background in data infrastructure, integration platform, or API-first product sales.
• Experience selling compliance or regulatory products to multinationals.
• Multinational sales cycle experience across multiple countries and legal entities.
• Experience at a category-defining infrastructure company at Seed or Series A stage.

What we Offer

• Huge market opportunity at the intersection of AI and global HCM, selling into a category we are defining.
• Validated traction from day one. Three of the top five global payroll providers already run on datascalehr, and Global Fortune 2000 enterprises are in active contracts and POCs.
• Real ownership. You shape GTM strategy and build the playbook the rest of the team will run, not someone else's spreadsheet.
• Compensation and equity: $250k - $350k OTE, uncapped commission, and meaningful equity as the first sales hire.
• We are a remote company, but this role is based in the New York / New Jersey area as the CEO is based outside NYC.  You should expect up to 30% travel for customer meetings, conferences and onsite events.

This is not necessarily an exhaustive list of all responsibilities, skills, tasks, requirements, efforts, or working conditions associated with the job. While this is intended to be an accurate reflection of the current job, datascalehr reserves the right to revise or change job duties and responsibilities as business needs arise. In compliance of ADA regulations, the employee must be able to perform essential functions with or without reasonable accommodation in a satisfactory manner, further accommodations shall not be made if it constitutes an undue hardship on this organization. datascalehr is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, national origin, disability, veteran status, or other characteristics protected by law.