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 workplace where change is common.
- You have strong sales acumen, effective time management and organization skills 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.

📌 Sales Enterprise Executive (Canada)
🏢 Digitail
📍 Canada