Enterprise Account Executive

Who We Are At Opkey, we empower enterprises to unlock the full potential of their ERP investments with cutting-edge, agentic AI-powered automation. Our intelligent platform delivers continuous assurance across the entire ERP lifecycle - from initial deployment to day-to-day operations and long-term digital transformation. By eliminating manual errors, accelerating testing cycles, and ensuring seamless adoption of critical updates, Opkey helps organizations modernize with confidence and agility. Trusted by 250+ global enterprises, we reduce risk, drive efficiency, cut costs, and fast-track innovation; so businesses can focus on what they do best: growing and evolving in a dynamic digital world. What We’re Looking For We’re looking for a closer. A strategist. A trusted advisor who delivers. Opkey is seeking an experienced Enterprise Account Executive to identify, cultivate, and close revenue opportunities for our complementary SaaS platform that supports and redefines ERP transformation. This role is ideal for someone who thrives in complex selling environments, has experience influencing large buying committees, and is highly fluent in enterprise digital transformation, automation, and operational risk narratives. You know how to build pipeline, qualify rigorously, and advance deals with purpose. You’re fluent in sales methodology and comfortable navigating enterprise procurement, legal, security, and value validation processes. You run toward competitive deals—not away from them—and you win through clarity, preparation, and persistence. This role may be remote for the right candidate, but will require travel to our Pittsburgh office and clients up to 30% of the time. This role requires experience in the Oracle or Workday related ERP/SaaS ecosystem(s). What You’ll Do Run a Full-Cycle Enterprise Sales Motion: Own the entire sales lifecycle - from prospecting and multi-threading, to business case development, to contract negotiation and close - with a focus on mid-six to seven-figure ARR opportunities. Pipeline Creation & Discipline: Develop pipeline through outbound prospecting, channel collaboration, referrals, and ABM inputs. Maintain accurate, data-driven forecasting in CRM and operate with high deal hygiene. Drive Enterprise ERP Ecosystem Sales: Engage stakeholders within the Oracle Cloud and Workday ecosystem, including business leaders, IT owners, system integrators, and transformation partners. Master Consultative & Value-Based Selling: Lead discovery, identify compelling pain sequences, articulate transformation value, shape solution fit, and tailor positioning to customer priorities and processes. Navigate Complex Buying Committees: Multi-thread across business, IT, finance, procurement, and risk stakeholders to advance deals, neutralize obstacles, and accelerate closure. Partner Cross-Functionally: Collaborate with marketing, solutions engineering, product, and customer success to win deals, support POCs, and ensure successful handoffs and long-term expansion. Champion Sales Methodology : Apply frameworks including MEDDPICCR, SPICED, or similar to qualify deeply, build mutual action plans, manage evaluation criteria, and ensure predictability of outcomes. A Day in the Life You’ll start by reviewing late-stage deals and setting up next best actions—confirming a mutual action plan with a Workday customer, prepping for an Oracle SI co-sell call, or tightening an ROI justification for procurement. Midday might be a deep-dive demo with an enterprise transformation leader or a discovery session mapping testing and release management challenges. You’ll sync with demand gen on pipeline coverage, or with Pre-Sales Engineering to design an evaluation plan for a high-value ABM target. You’ll update Hubspot, refine forecasts, and work with rigor to advance opportunities. Every day blends strategy, execution, and competitive selling—if you thrive in big, complex motions, this is your lane. What You’ll Bring 4+ years of B2B enterprise sales experience, ideally in SaaS, services, or automation Consistent success closing six- and seven-figure enterprise deals Experience selling into Oracle Cloud (Fusion) and/or Workday ecosystems required. Understanding of enterprise transformation, business process automation, or ERP modernization Mastery of sales methodologies including MEDDPICCR, SPICED, or comparable frameworks Skilled in multi-threading, objection handling, and competitive positioning Strong business case development and executive presentation skills CRM discipline and forecasting accuracy (HubSpot, Salesforce, or similar) Collaborative mindset with a bias toward preparation, learning, and iteration Comfortable commuting to Pittsburgh office + traveling to enterprise clients as needed Bachelor’s degree preferred Equal Opportunity at Opkey At Opkey, we’re building a team as diverse and dynamic as the customers we serve. We are proud to be an equal opportunity employer and welcome candidates of all backgrounds, experiences, and perspectives. Direct applicants only, no recruiters. Compensation DOE.