Sales Enterprise Executive

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

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.

#J-18808-Ljbffr