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• GTM Ops & AI

• Indefinite
• Full time
• Hybrid (Ontario, Canada)

Digitail is transforming veterinary care through bold, customer-first technology. Our all-in-one operating system empowers animal hospitals to seamlessly manage client communication, patient records, scheduling, billing, and more. Backed by top-tier investors - Gradient Ventures (Google’s AI fund), byFounders, Partech, Atomico, and Five Elms Capital - we're driven by a deep love for pets and respect for veterinary professionals.

We’re seeking a seasoned professional to lead GTM Ops & AI who brings strategic oversight, technical depth, and an AI-first mindset to power and scale our revenue engine. You’ll unify our GTM operations, architect automation across the revenue stack, and serve as the CRO’s right hand in shaping an AI-powered GTM motion.

What You’ll Do

1. Unify & Optimize Go-to-Market Operations

• Align Sales, Marketing, and Customer Success with shared revenue goals and KPIs (pipeline velocity, CAC, LTV, churn).

• Streamline lead handoffs, pipeline analytics, forecasting, deal inspection, and CAAR → ARR velocity.

• Manage GTM commission reporting, revenue analytics, and operational governance.

• Centralize GTM data and maintain consistent revenue architecture across teams.
  

2. Build & Orchestrate the GTM Tech Stack

• Architect integrations across CRM (HubSpot), sales engagement, marketing automation, AI agent platforms, and analytics tools.

• Design and maintain a scalable tech stack that minimizes manual work and maximizes automation.

• Automate workflows: lead scoring, enrichment, cadences, outbound sequences, SDR automation, Support Fin AI agent, and data pipelines.

• Build systems to support scalable pipeline generation and improved conversion efficiency.
  

3. Implement AI-Powered Automation & Experimentation

• Own the strategy and execution of AI-first GTM workflows - embedding automation into every stage of the GTM lifecycle.

• Rapidly prototype, test, and scale AI-powered workflows using agentic AI platforms, API-first builders, and automated enrichment tools.

• Design AI-driven outreach (personalized messaging, multi-channel sequences) supported by prompt-engineered workflows.

• Lead quarterly innovation initiatives: dynamic segmentation, AI-driven prospecting, workflow automation, and funnel experiments.
  

4. Ensure Data Integrity & Actionable Insights

• Maintain CRM accuracy and completeness - ensuring it functions as the single source of truth.

• Develop executive-level dashboards and reporting across revenue touchpoints (forecasting, pipeline, retention).

• Conduct ROI analyses, track AI and automation performance, and drive data-informed decision-making.

• Build automated data pipelines to support ICP definition, targeting, and segmentation.
  

5. Enable Cross-Functional Collaboration

• Serve as the CRO’s partner in driving AI-first GTM transformation.

• Educate GTM teams on AI-enabled workflows, new tools, and best practices.

• Collaborate with Product, Marketing, Sales, CS, and RevOps to support launches, campaigns, expansion strategies, and customer lifecycle improvements.

• Document and implement streamlined sales processes to increase consistency and adoption.

You Bring

• 4–7+ years in revenue operations, sales operations, GTM engineering, or AI-enabled growth roles.

• Experience in high-growth B2B SaaS environments (RevOps + AI/automation experience strongly preferred).

• Deep proficiency with:

  • HubSpot, Salesforce (bonus), Intercom, marketing automation

  • Sales engagement platforms (Outreach, Amplemarket, Lemlist, SalesLoft)

  • AI-driven prospecting tools (Clay, ChatGPT API, agent platforms)

  • Automation tools (Zapier, Workato)

  • APIs, data modeling, and integration workflows

• Strong analytical mindset with experience building dashboards, modeling revenue metrics, and optimizing funnels.

• Ability to manage complex cross-functional projects end-to-end.

• Exceptional communication - you can translate technical systems into strategy and influence adoption.

• High-agency, founder-like mindset: you iterate quickly, seek clarity, and move fast while maintaining quality.

• Bonus: Hands-on experience: scripting (SQL, Python/JS), enrichment tools, attribution models, and predictive analytics.