Account Executive
Account Executive – Association Market
Sidecar
Full-Time | Sales | Association Market Focus
About Sidecar
Sidecar is the leading AI education platform built exclusively for association professionals. Through Sidecar’s Learning Hub for Teams, associations can train their entire organization on AI with role-specific learning tracks, a professional development certification, and strategic advisory support. Sidecar is on a mission to help the association community lead the AI transformation, not fall behind it.
About the Role
We're looking for a consultative, relationship-driven Account Executive to help grow Sidecar's new business. You'll be selling directly to association executives- CEOs, COOs, IT Directors, HR leaders, etc. with the goal of helping them understand why AI fluency is now a strategic imperative and how Sidecar is the right partner to get them there. This is a full-cycle role with significant upside for someone who knows the association space. Sidecar is in a period of significant growth, and this role offers real advancement opportunities for the right person. Candidates should expect a demanding schedule as weeks of 50+ hours are common, and efforts often extend outside traditional business hours. We're looking for someone who is motivated by that kind of environment and the opportunity it represents.
What You'll Do
- Own a pipeline of trade associations, professional societies, and membership organizations from first conversation through close
- Run discovery calls and demos that connect Sidecar's platform (Foundation, Growth, and Enterprise tiers) to each prospect's specific organizational goals and challenges
- Navigate consensus-driven buying at associations (boards, leadership teams, department heads) with patience and clarity
- Manage deals ranging from ~$4K to $250K+ depending on org size and product fit
- Partner with Customer Success on handoffs to drive retention and expansion revenue
- Represent Sidecar at association industry events
- Maintain accurate forecasting and CRM hygiene
What We're Looking For
- 1-3 years of B2B SaaS sales experience with a consistent record of exceeding quota
- Direct experience selling into associations, nonprofits, or membership organizations with an understanding of how they buy, who holds the budget, and how boards influence decisions
- Genuine passion for AI and the opportunity it represents for the association community
- Consultative selling skills to lead with curiosity and business impact, as opposed to feature lists
- Comfortable with revenue-based pricing models and multi-stakeholder sales cycles (30–120 days)
- Familiarity with ASAE, association industry events, or the broader association technology ecosystem is strongly preferred
- Proficiency with HubSpot, Salesforce, or similar CRM
Why Sidecar
- Sell a category-defining product in a market you already know and care about
- Clear, transparent pricing model that enables honest, consultative conversations
- Ground-floor opportunity to help shape how the association world adopts AI
- Competitive base & OTE
- Collaborative, driven team culture with a clear path to professional growth