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Account Executive, Enterprise

Plane· Go-To-Market (GTM)
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CanadaFull-timePosted 2mo ago

About the role

Enterprise-focused Account Executive responsible for full-cycle, end-to-end sales to technical buyers in regulated industries, aligning product-led growth with complex procurement and security requirements and contributing to the sales playbook and product feedback.

Responsibilities

  • Run deals end-to-end — from first enterprise inquiry to signed contract. You own the entire arc: discovery, demo, technical evaluation, security review, procurement, negotiation, close.
  • Convert product-led interest into enterprise revenue — engage self-hosting users hitting compliance or scale ceilings and guide conversations to deployment.
  • Navigate complex enterprise procurement in aerospace, defense, healthcare, and finance (security questionnaires, compliance reviews, legal redlines, multi-stakeholder approvals, multi-month timelines).
  • Hold technical credibility in conversations with VPs of Engineering, DevOps leads, and IT architects about self-hosted deployments, air-gapped environments, SSO configurations, and data residency requirements.
  • Build and refine the sales playbook — identify objections, typical deal cycles, bottlenecks, and missing collateral.
  • Feed product with deal intelligence — communicate market signals, competitor moves, and gaps back to the product team in a structured way.

Qualifications

  • Closed enterprise software deals in the $500K–$1M ACV range, full-cycle ownership.
  • Experience selling to technical buyers (engineering leadership, DevOps, IT) with knowledge of deployment models, infrastructure, and security.
  • Experience at an early-stage company (Series A or earlier) building pipeline, sequences, collateral, and motion.
  • Understanding of product-led growth and how to leverage free tiers as a funnel while knowing when to engage for enterprise.
  • Comfort with long deal cycles and multi-stakeholder procurement processes (4+ months, legal/security/compliance/IT vetoes).
  • Structured pipeline management and disciplined note-taking/follow-ups.
  • Ability to write clear follow-up emails, proposals, and internal summaries.

Skills

Required:Full-cycle enterprise salesTechnical credibility with engineering leadershipProduct-led growth fluencyProposal and email writing

Benefits

  • Competitive compensation structure (base + variable)
  • Opportunity to influence product direction and sales playbooks
  • Work with cutting-edge AI/automation in a regulated, enterprise-focused environment
  • Collaborative, cross-functional environment with direct interaction with CEO and product team
  • Equal opportunity employer; commitment to diversity and inclusion
Last updated Aug 19, 2026. Interested? Apply on the company site.
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The Open Source Project Management Tool

Open-source project management that's simple, extensible, and loved by teams.

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