Enterprise Account Executive - $250K to $300K OTE - AI Automation for Insurance & Financial Services

RevsUp represents a rapidly scaling AI automation company that is transforming back-office operations in the insurance and financial services industries.This 35-employee, Series A firm ($11.65 million from Neotribe Ventures and AZ-VC), is hiring an Enterprise Account Executive to sell $100K to $400K+ ACV SaaS solutions to third-party administrators (TPAs) and insurance organizations located across the United States. You will report to the VP of Sales and can work remotely with optional access to a Scottsdale, Arizona office.SolutionThis is an AI-powered automation platform purpose-built for third-party administrators (TPAs) and insurance organizations. The platform streamlines complex back-office workflows by extracting, classifying, and processing unstructured data from documents"”replacing manual, people-heavy processes with intelligent automation.With solutions tailored to trust accounting and customer experience, the platform enables firms to modernize operations, boost efficiency, and reduce reliance on outsourcing and legacy tools.Role • Full-cycle, quota-carrying AE role reporting to the VP of Sales. • $125K to $150K base with $250K to 300K OTE; uncapped, monthly commissions with accelerators. • Own a $1.5M quota selling CX solutions ($100K-$400K ACV) and TA solutions ($50K-$75K ACV). • Work remotely, with ~25% travel to home office, conferences, trainings, and meetings. • Engage C-level decision-makers in long-cycle, complex deals; especially in CX automation. • Must have 5 to 10 years of B2B SaaS sales experience, ideally in early-stage or CRM-lite/workflow automation sectors. • Requires experience selling into complex buying groups with a Challenger-style approach.Culture • Series A company with $11.65M in funding from Neotribe Ventures and AZ-VC. • 35-person team headquartered in Scottsdale, AZ; collaborative environment with clear TAM and leadership access. • Strong GTM motion with SDR support, webinars/events, and marketing content. • Benefits include full medical/dental/vision, unlimited PTO, paid parental leave, QACA 401(k), equity, and stocked office.Official Job DescriptionThe RoleThis role owns and expands the enterprise motion across a focused, high-value market of third-party administrators and insurance-related organizations. This role is a full-cycle, quota-carrying position responsible for sourcing, developing, and closing complex, high-ACV opportunities"”primarily for customer experience automation solutions.This is a hybrid role with flexibility to work remotely anywhere in the U.S. Travel of approximately 25% is expected for conferences, trainings, and key customer engagements. The Enterprise AE works closely with executive leadership, product, and marketing.Responsibilities • Own a $1.5M annual quota focused on enterprise accounts, with no fixed geographic territory • Run full-cycle sales motions from discovery through close on complex, multi-threaded deals • Sell high-ACV CX automation solutions (typically $100K-$400K ACV) and Trust Automation solutions ($50K-$75K ACV) • Execute top-down, consultative sales motions with executive buyers including Owners, COOs, CTOs, and Heads of IT • Lead strong discovery to uncover operational pain, competing priorities, and ROI drivers tied to automation and workflow replacement • Evangelize the platform's value by helping prospects understand the cost of manual work, outsourced operations, and legacy tools • Drive urgency and momentum in longer, variable enterprise sales cycles • Collaborate closely with SDRs, product, and marketing to refine messaging, demos, and go-to-market strategy • Maintain strong CRM hygiene and forecasting accuracy using HubSpot and outbound toolsQualifications • 5-10 years of B2B SaaS sales experience, with demonstrated success in enterprise or complex mid-market environments • Proven track record of closing six-figure ACV deals and consistently carrying $1M+ quotas • Startup experience required; candidates with only large-enterprise backgrounds are not a fit • Strong discovery, demo, and objection-handling skills in legacy-replacement or zero-competition environments • Comfortable multi-threading and navigating complex buying committees • Experience selling workflow automation, back-office software, or CRM-lite platforms preferred • Familiarity with Challenger-style sales motions is strongly preferred • Proficiency with modern sales tools (HubSpot, Apollo, Outreach or similar)Compensation & Benefits • Base Salary: $125,000-$150,000 • On-Target Earnings (OTE): $250,000-$270,000 (uncapped) • Commission Structure: Tiered accelerators ranging from approximately 7%-22% • Equity: Included • Benefits: o Full medical, dental, and vision coverage o Unlimited PTO o Paid parental leave o 401(k) with QACA match (100% of first 1%, 50% of next 5%) o Monthly commission payouts o Free lunches and stocked office for in-office daysLocation & Travel • Open to candidates nationwide within the United States • Work remotely with optional access to the Scottsdale, AZ headquarters • Approximately 25% travel for conferences, trainings, and customer meetingsWhy Join • Clear, focused enterprise TAM with real operational pain and strong ROI drivers • Series A company with momentum, strong leadership access, and room to build process • Collaborative, high-caliber sales team with strong product and executive support • Opportunity to sell transformational automation technology into a traditionally underserved market • Meaningful upside and career growth as the company scales its enterprise motion

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