Sales Enterprise Executive

Toronto - Canada

Monthly Salary: Not Disclosed

Posted on: 2 hours ago

Vacancies: 1 Vacancy

Job Summary

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 valuenot 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 lifecyclefrom 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 in-office (Toronto) & remote culture
Generous paid time off
Mission-driven company serving veterinary clinics

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.

About DigitailDigitail 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...