Sales Enterprise Executive (Remote)

Tech Sales Jobs; United States; Remote; USD 85,000 - 120,000; Full time

Benefits offered by this job

Work from home stipend

Awesome remote culture

Generous paid time off

Job summary

Digitail is hiring a Sales Enterprise Executive for an experienced, senior sales professional. You will own end-to-end enterprise sales motions to veterinary groups, engaging C-suite stakeholders and guiding multi-location buyers through complex evaluations.

Remote role with opportunity to travel for executive meetings and industry events. You will partner with onboarding and product teams to ensure a smooth handoff from sale to launch, and you will consistently exceed revenue targets through

Qualifications

• Experience selling SaaS into enterprise veterinary groups
• Comfort engaging C-suite and senior leadership stakeholders
• Proven ability to manage RFQs, RFPs, pilots, and formal evaluation processes
• Willingness to travel for executive meetings and industry events

Responsibilities

• Own complex, full-cycle enterprise sales motions from discovery through close
• Lead consultative buying processes with multiple stakeholders including owners, sponsors, operators, and clinical leaders
• Conduct structured, outcome-driven demos mapping current-state workflows to future-state impact
• Maintain deal momentum with disciplined follow-up, stakeholder alignment, and next steps

Job description

Sales Enterprise Executive

Location: Remote

Eligible to candidates in Canada & most U.S. States

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.