Account Executive, SMB

Overview

Account Executive (Velocity) - Caddie is hiring on behalf of a remote-first, Series A AI startup building an AI-powered Chief of Staff for modern teams.

Location: Remote (Canada)

Base Salary: $60,000 – $80,000 CAD

OTE: $120,000 – $160,000 CAD (50/50 split)

Our client’s product helps employees get more value from meetings by capturing discussions, surfacing insights, answering questions, and taking action using AI. The company is well-funded, backed by top-tier venture capital, and led by founders with previous successful exits.

They serve thousands of customers globally, from fast-growing startups to well-known mid-market and enterprise brands, and consistently earn top customer satisfaction ratings.

As part of continued growth, they’re expanding their sales team and hiring an Account Executive to help drive revenue in the SMB and Mid-Market segment. While candidates based in Canada are preferred, US-based candidates may be considered for the right fit.

• 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 Hub Spot CRM

• Minimum 1 year of experience selling SaaS
• Experience working in a product-led growth (PLG) environment strongly preferred
• 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

Our client is committed to building a diverse and inclusive team and provides equal opportunity regardless of race, ethnicity, religion, age, sex, sexual orientation, gender identity or expression, marital status, family status, disability, or other protected characteristics. Accommodations are available throughout the hiring process upon request.