Founding Account Executive — CollectWise

Location: Manhattan, NY (Onsite) | Compensation: $100,000 – $150,000 base

• OTE $200,000 – $300,000 + uncapped commission | Equity: 0.1% – 0.5%

About CollectWise

CollectWise is a YC-backed AI startup automating debt collection in a $35B US market. Their AI agents are already outperforming human collectors by 2x at a fraction of the cost. With a team of five, the company has scaled to a $2M annualized run rate and is targeting $10M ARR within the year.

The Role

This is the first dedicated sales hire. You will partner directly with the founder to build and scale the entire sales motion from the ground up. The product has already proven strong demand, and the role exists to expand capacity and accelerate growth.

What You'll Do

• Own the full sales funnel from first touch through close
• Run high volumes of demos and sales calls, up to 8 to 12 per day
• Build pipeline through outbound prospecting, relationship-driven selling, and creative sourcing
• Leverage referral pipelines that contribute 30 to 50 percent of opportunities
• Attend conferences, trade shows, and industry events to generate leads and relationships
• Work directly with the founder to refine messaging, positioning, pricing, and demo flow
• Navigate complex enterprise sales cycles across executives, legal, compliance, and procurement stakeholders
• Ensure signed customers successfully go live, as commission is tied to active revenue usage

Sales Context

• Average contract value: $100,000 with outliers from $300,000 to $500,000
• Sales cycle: Under one month
• Quota: $1M to $1.5M ARR annually
• Pipeline: 30 to 50 percent partner-sourced, 50 to 70 percent self-generated
• Commission: Uncapped, top performers exceeding $2M ARR can reach $400K+ OTE

What We're Looking For

• 3+ years as a full-cycle Account Executive in enterprise or complex B2B sales
• No SDR to AE progression without full ownership experience
• Proven record of closing $5M+ ARR with clear revenue metrics on resume
• Experience scaling a company from approximately $1M to $10M+ revenue
• Ability to independently build pipeline and operate without structured support
• Strong consultative and ROI-driven selling approach
• Experience navigating multi-stakeholder enterprise deals
• Must be based in or willing to relocate to NYC and work onsite
• Willing to travel approximately once per month for events

Interview Process

Intro call with Founder and CEO → Mock sales call → Reference checks → Offer