Enterprise Account Executive - Chicago, USA

Enterprise Account Executive - Chicago, USAUnited StatesSingleStore is looking for an accomplished sales professional to join our Sales Team. AI is moving from experimentation into production, and this role is an opportunity to break into AI while doing meaningful enterprise selling.As an Account Executive, AI Hunter, your job is simple: create new SingleStore customers. You will find companies building AI applications where data access, real-time context, memory, retrieval, or operational scale is becoming a constraint—and turn those challenges into new SingleStore customers. You will own a broad territory, build a majority self-sourced pipeline, create demand in an emerging category, and close greenfield enterprise opportunities.This is a true hunting role. You will engage customers before they have a defined project, develop customer-specific points of view, create urgency around business and technical problems, work with technical experts to land first production workloads, and build a measurable new-logo business with broad ownership. The ideal candidate is a measurable enterprise hunter who is competitive, curious, technically credible, resilient, and able to sell business outcomes. Direct AI sales experience is valuable, but proven selling ability and technical curiosity matter more than a narrow "AI seller" title.Role and ResponsibilitiesBuild and execute a territory strategy for net-new customer acquisition.Prospect fearlessly across a broad account universe using proactive, persistent outbound, account-based, partner, and market-education motions; stay resilient and effective through rejection and ambiguity.Form account hypotheses, map the buying center, and earn first meetings with relevant points of view tailored to the customer.Engage executive, business, technical, security, and procurement stakeholders.Lead great business-first discovery, connect AI and data challenges to fundable goals, and build quantified ROI, TCO, or operational-impact cases.Build and develop champions, multi-thread the buying group, earn executive and economic-buyer access, and maintain stakeholder alignment; own the stakeholder plan, mutual action plan, close plan, value case, stage gates, forecast, and commercial outcome.Lead complex sales cycles through technical validation, security, legal, procurement, negotiation, and close.Partner with Solutions and Forward Deployment Engineers and cross-functional teams to validate technical fit and establish the first production workload.Navigate competitive displacement and maintain disciplined activity management, CRM hygiene, reporting, qualification, forecasting, and opportunity management; showcase clear metrics such as pipeline created, meetings, conversion, quota attainment, and new-logo performance.Be AI fluent: use AI and research tools productively and responsibly while applying judgment, validating outputs, and separating facts from hypotheses.Travel within the assigned territory as required.Required Skills and Experience5+ years of quota-carrying B2B enterprise software sales experience, ideally selling to large or technically sophisticated organizations; experience in data, cloud, analytics, AI, or adjacent technical domains is a plus.Repeated, quantified quota success with clear ownership of new-logo wins and self-sourced pipeline.Experience closing complex, multi-stakeholder deals involving executives, technical evaluators, security, legal, finance, procurement, and partners.Ability to sell measurable business outcomes and build ROI, TCO, or operational-impact cases.Technical fluency in an adjacent domain such as databases, data infrastructure, analytics, AI/ML, cloud, Kubernetes, developer tools, cybersecurity, observability, or open-source software.Strong qualification, account planning, forecasting, CRM, negotiation, and deal-management skills.Learning velocity and coachability, demonstrated through specific behavior change after feedback; ability to explain technical concepts clearly to technical and executive audiences.Executive presence, customer trust, resilience, intellectual honesty, and excellent communication skills.B.A., B.S. degree or equivalent in a related field.Experience with Fortune 500 or security-sensitive organizations, cloud ecosystems, open-source or consumption-based products, or emerging categories is preferred.