Sales Enterprise Executive

This role is available as a remote position in the United States or as a hybrid position in Canada. About Digitail Digitail is the AI operating system for modern veterinary clinics. Digitail continuously improves how practices run — from client communication and scheduling to medical records, billing, and payments — so teams can focus on care, not admin. Unlike traditional PIMS that expect clinics to bend their workflows around clunky software, Digitail delivers a proven operating system designed and refined alongside veterinary teams. Digitail brings ten-plus tools into one intelligent platform, with built-in workflows and AI assistants working behind the scenes — giving growing clinics and established groups a shared system that scales with their operations, not against them. This role is for a senior, consultative sales professional with proven success selling software to enterprise veterinary groups . You are comfortable engaging C-suite stakeholders, navigating complex buying committees, and leading long-cycle, high-stakes decisions. You own end-to-end deal strategy and engage the right internal partners to advance multi-stakeholder enterprise opportunities. What You Will Do Own complex, full-cycle enterprise sales motions from initial discovery through negotiation, close, and handoff Lead consultative buying processes with multiple stakeholders, including practice owners, executive sponsors, operators, and clinical leaders Act as a trusted advisor, helping organizations evaluate change, mitigate risk, and align around a clear decision Run structured, outcome-driven demos that map current-state workflows to future-state operational and clinical impact Diagnose operational friction and translate it into quantified business, financial, and care-delivery outcomes Build and manage deal momentum through disciplined follow-up, stakeholder alignment, and clear next steps Navigate longer sales cycles by guiding buyers through evaluation, internal alignment, and approval processes Develop deep expertise in the product, market, and veterinary operating models to advise at an executive level Partner closely with onboarding, customer success, and product teams to ensure a seamless transition from sale to launch Own pipeline inspection, forecasting accuracy, deal strategy, and consistently exceed revenue targets How You Think & Solve Problems Discovery-first and hypothesis-driven, seeking to understand root causes before proposing solutions Comfortable operating in ambiguity and guiding buyers through complex, high-stakes decisions Oriented around business outcomes, workflow transformation, and long-term value—not feature comparison Able to connect technical and operational detail to executive-level priorities and risk considerations Skilled at simplifying complexity and communicating clearly across technical, clinical, and non-technical audiences Data-informed and structured in your thinking, using frameworks to drive clarity and alignment Proactive in leveraging technology, automation, and AI to increase leverage and scale impact Strong sense of ownership across the full deal lifecycle—from first insight to signed agreement and beyond Resilient, adaptable, and comfortable iterating your approach as deal dynamics, stakeholders, and priorities evolve Your Experience Demonstrated success selling SaaS into enterprise or multi-location veterinary groups Experience engaging C-suite and senior leadership stakeholders Comfort managing RFQs, RFPs, pilots, and formal evaluation processes Existing relationships and industry credibility within veterinary enterprise networks preferred Comfort working remotely and asynchronously Willingness to travel for executive meetings and industry events History of personal and professional excellence Lifelong learner mindset and commitment to professional growth and development You thrive while working in a fast-paced environment where change is common. You have strong sales acumen, effective time management and organization skills Compensation + Benefits Generous salary + uncapped commission and a pre-IPO equity package. Work from home stipend to set up your office Awesome remote culture Generous paid time off Mission-driven company serving veterinary clinics Salary Range 85-120k in local currency Final Note for Candidates This role is for enterprise sellers who value trust, accountability, and long-term relationships. You will be expected to lead complex conversations, manage multiple stakeholders, and own outcomes across large, strategic deals.