[Remote] Account Executive, SMB

Remote, USA
Posted Jun 14, 2026
Full-time

Note: The job is a remote job and is open to candidates in USA. Caddie AI is a remote-first, Series A AI startup creating an AI-powered Chief of Staff for modern teams. They are seeking an Account Executive to drive revenue in the SMB and Mid-Market segment by closing inbound leads and managing deals with multiple stakeholders.

Responsibilities

  • Close a high volume of inbound leads using your SMB SaaS sales experience
  • Manage and quarterback deals with multiple stakeholders
  • Work directly with C-level executives and business owners to understand challenges and propose solutions
  • Develop deep product knowledge to help customers achieve their desired outcomes
  • Drive high customer satisfaction, retention, and long-term value
  • Maintain accurate records of all customer interactions in HubSpot CRM

Skills

  • Minimum 1 year of experience selling SaaS
  • Proven success closing deals in the $5K–$10K+ ARR range
  • Track record of strong sales performance
  • Comfortable operating in ambiguous, fast-changing environments
  • Strong negotiation and communication skills
  • Self-starter with a bias toward action and ownership
  • Highly organized with strong attention to detail
  • High emotional intelligence and customer empathy
  • Experience working in a product-led growth (PLG) environment strongly preferred

Company Overview

  • Caddie AI is the global hiring marketplace built for tech startups. It was founded in 2024, and is headquartered in San Francisco, California, US, with a workforce of 2-10 employees. Its website is https://www.hirecaddie.ai/.

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