Sales Enterprise Executive

Sales Enterprise Executive

- Indefinite

- Full time

- Hybrid (M5V 2G9, Toronto, Ontario, Canada)

- Sales & Marketing

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 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.

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