Founding Account Executive

Founding Account Executive

WaySky | Contractor to start | 10% commission on collected revenue

WaySky helps companies get recommended by ChatGPT.
We do that by improving the internal trust signals, public proof, and credible third-party coverage AI systems rely on when deciding which businesses to surface. We’ve built technology that can diagnose a company’s AI visibility and AI trust score in minutes. Those diagnostics open the door to paid follow-on work: Fix Packs, Source Sprints, and Visibility Retainers.
We’re looking for a founding AE who can sell that work clearly, confidently, and without hype.

Who you’ll sell to

• VP Marketing
• Head of Growth
• Product Marketing leaders
• Founders / owners These are smart buyers. They will ask hard questions. You need to be able to handle that.

What you’ll be selling:
You’ll own the motion from first outreach to close, converting qualified accounts into:

• Fix Pack — starting at $15K
• Source Sprint — $7,770 to $55,770+
• Visibility Retainer — starting at $5K/month

What the job actually is:
This is not a “spray and pray” SDR role.
You will:

• run outbound across email, LinkedIn, and phone
• qualify aggressively and walk away from weak fits
• run discovery with senior marketing leaders
• present the offer clearly
• close premium, consultative deals
• keep pipeline and notes clean in the CRM
• work directly with the founder to improve messaging, objections, and pricing based on real conversations

What success looks like in the first 30 days

• You can book and run discovery calls without hand-holding
• You close your first Reality Checks
• You develop a repeatable talk track that converts
• You can confidently explain why WaySky is not “paying for fake reviews” and how our model relies on disclosures and honest evaluations

Requirements

Non-negotiable:

• 3+ years selling to marketers (VP Marketing, Growth, PMM)
• Proven ability to close $15K–$100K+ deals in SaaS or services
• Strong written outbound — your emails do not sound like spam
• Comfortable selling directly and honestly: no fluff, no hype
• Can handle objections around ethics, trust, and “will this actually work?”

Nice to have

• Experience selling SEO, content, PR, review platforms, analyst relations, or agency services
• Familiarity with B2B SaaS categories like RevOps, sales tech, or martech
• Experience selling retainers
• Comfortable selling a structured diagnostic first

Compensation

• Contractor to start
• 10% commission on collected revenue