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Founding Account Executive

Willow· Sales
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Hybrid (San Francisco, CA)$200k - $300kFull-timePosted 7mo ago

About the role

Willow is a voice dictation app building a voice operating system. The Founding Account Executive will be the first dedicated sales hire, turning product-led demand into enterprise revenue and building a scalable GTM playbook in collaboration with the CEO and GTM advisory team.

Responsibilities

  • Run full-cycle deals from first conversation through close. You own the pipe, the relationship, and the outcome.
  • Convert product-led demand into enterprise revenue. Identify high-potential accounts, find and enable champions, and turn organic adoption into commercial deals.
  • Build and execute the expansion motion across departments within existing logos.
  • Systematize inbound and prioritize pipeline using usage/signup data to surface high-intent accounts.
  • Navigate enterprise deal mechanics with IT, security, and procurement; handle security questionnaires, negotiate contracts, structure pilots, and manage multi-threaded deal cycles.
  • Shape the sales narrative in collaboration with the founding team on positioning, objection handling, competitive differentiation, and pricing strategy.
  • Document learnings to become the foundational playbook for the GTM team.

Qualifications

  • 2-5+ years in full-cycle enterprise B2B SaaS or developer-focused/productivity companies.
  • Experience selling into enterprise with IT, security, and procurement stakeholders.
  • Founding AE, first sales hire, or early GTM at a company needing to build from scratch.
  • Experience converting bottom-up product adoption into top-down commercial relationships (PLG-to-SLG).
  • Strong systems-thinking approach with CRM hygiene, pipeline management, outbound tooling, and AI-powered workflows.
  • Clear, empathetic communicator able to engage founders, IT directors, CTOs, and COOs.
  • Strong ownership mindset and proactive problem-solving.

Skills

Required:Full-cycle enterprise salesAccount expansion / land-and-expandOpportunity management & pipelineStakeholder navigation (IT, security, procurement)
Last updated Aug 26, 2026. Interested? Apply on the company site.
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About Willow

The voice interface replacing your keyboard

Willow is an AI dictation app that lets you type with your voice. Built to 4x the productivity of anyone spending too much time on email, docs, and AI prompting workflows. We’re Mac-only for now. You can try it free at WillowVoice.com

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