Enterprise Account Executive

Digitail is the leading cloud-based, AI-native platform built to power every part of a veterinary clinic — scheduling and intake, medical records, invoicing, inventory, client communication, and a connected pet parent app. Founded in 2018 by Sebastian Gabor and Ruxandra Pui, the company set out to fix a category that had barely changed in decades: veterinary teams working across disconnected, outdated tools while drowning in admin. The platform replaces dozens of point solutions with one system, and it was designed for AI from the ground up rather than retrofitted. A fleet of 15+ AI agents handles intelligent patient intake, dictation for SOAP notes, automated record summaries, and treatment planning — saving clinics 50+ hours a month in administrative work and helping teams see up to 2x more patients per day. Digitail more than doubled its customer base in the last twelve months and now supports over 10,000 veterinary professionals and 3 million pet parents. In November 2025 the company raised a $23M Series B led by Five Elms Capital to accelerate AI development and scale globally. This is a company growing fast in a category that is finally ready to modernise. Highlights:Founded in 2018 by Sebastian Gabor & Ruxandra Pui, named to Forbes 30 Under 30 Europe (2023)Rated #1 in veterinary practice management software by its user baseTheir AI-powered veterinary assistant automates SOAP notes, patient summaries, treatment planning, patient intake, etcIn the past 12 months, Digitail has more than doubled its customer base.$23M Series B led by Five Elms Capital (Nov 2025); $37M+ raised to dateInvestors include Five Elms Capital, Atomico, Partech, byFounders and Gradient Ventures10,000+ veterinary professionals and 3M+ pet parents on the platformCustomer base more than doubled in the past 12 monthsOffices in Toronto (go-to-market), Iași, Romania (product and engineering), and London, plus a distributed US team15+ AI agents and 30+ integrations in a single platformInnovator of the Year, Tekpon Awards 2024Go-to-market led by CRO Daniella Bellaire, previously Head of Sales at Shopify About the Role:Digitail has product-market fit, a category-leading platform, and real momentum. The next opportunity is to build the enterprise motion around it — targeting the consolidators, corporate groups, and multi-location practices that represent the largest and most strategic opportunities in the market. As an Enterprise Account Executive, you’ll report directly to CRO Daniella Bellaire, with visibility and access to the executive team and co-founders. You’ll own the US and Canadian enterprise territory and have the opportunity to build a team underneath you as the motion scales. Please note: this is a remote, US-based role, with a preference for candidates in the East Coast or Central time zones.Own the full enterprise sales cycle across veterinary consolidators, corporate groups, and multi-location practices throughout the US and CanadaClose high-value, complex deals typically ranging from $70–100K in subscription ARR on 3–5 year terms, with the opportunity to attach Digitail’s payments product and approximately double the overall deal valueNavigate sophisticated buying processes involving multiple stakeholders, while building credibility with practice owners, operators, and CEOsLead the pilot motion end-to-end — shaping the pilot rubric, setting expectations, establishing success criteria, and converting successful pilots into broader rolloutsBuild the enterprise sales motion from the ground up, including messaging, qualification, sales process, pilot design, stakeholder mapping, and rollout strategyTurn what works into a repeatable playbook — defining the enterprise sales process, documenting it, and creating the foundation for future hires to scaleBring the market back into Digitail, sharing intelligence on competitors, buying triggers, customer needs, and where Digitail has a meaningful advantageWork cross-functionally throughout the sales process with outbound BDRs, Forward Deployed Engineers/Solution Engineers, Account Managers, and senior leadershipOwn pipeline, forecasting, and deal discipline, bringing rigor and visibility to a growing enterprise businessHelp shape Digitail’s broader GTM strategy, refining the enterprise proposition, positioning, messaging, and approach as the market evolvesAct as the voice of the enterprise customer, bringing insights back to Product, Marketing, and leadership to influence roadmap, positioning, and future growth About You:You’re a strategic, polished enterprise seller who knows the veterinary industry and can build credibility with senior leaders. You’re comfortable navigating complex buying environments, selling innovative technology, and helping customers understand the business impact of changing the way they operate. You’re equally comfortable closing large deals and helping build the processes needed to scale an emerging enterprise sales motion. Strong experience selling within the veterinary industry, ideally to large groups, consolidators, or multi-location organizationsEstablished veterinary industry relationships and a strong understanding of how larger veterinary organizations operate and buyProven enterprise sales experience managing complex, multi-stakeholder sales cyclesExperience navigating large or multi-year commercial agreementsStrong executive presence with the ability to engage and influence C-suite stakeholdersExperience selling innovative technology, SaaS, AI-enabled products, or other workflow-changing solutionsAbility to translate operational challenges into clear business cases and commercial valueComfortable building sales processes, messaging, and playbooks in an evolving startup or scale-up environmentStrong negotiation, forecasting, pipeline management, and commercial skillsComfortable with AI technology and able to clearly articulate its impact on veterinary workflowsExperience within a large veterinary lab, animal health company, or similar organization may also be relevant where there is strong regional sales experience and an established veterinary network The Extras that Matter:This is the first enterprise seller at a company that just doubled its customer base and raised a $23M Series B. You're not inheriting a playbook — you're writing it, and the ceiling on this role goes as far as you take it. What they’re building matters - it impacts the lives of real people and pets 🐶Comprehensive health coverage with generous PTOCareer growth opportunities within a rapidly scaling global organizationA modern AI-powered outbound stackYearly budget for learning and growth opportunitiesCompetitive compensation & equity - designed to provide you with financial security Compensation: $130K-$150K base, $260K-$300K OTE (USD)