Sailes is the market-leading, authentic, AI for Sales on Autopilot for the Fortune 500+. Our patent-pending, personality driven AI autonomously completes every step of the sales prospecting process - from research and discovery to data enrichment, intelligent interaction, objection handling, and social media engagement - hands-free.

Beyond sales enablement agents, our Sailebots are a true Digital Labor solution that multiplies the power of world class AEs by 16X.

Sailes is Sales with AI and we’re looking for a dynamic and proven renaissance AE to serve on a select team within our organization.

Your Mission:

As an AI Account Executive at Sailes, you will be responsible for acquiring net new customers (targeting companies with 200+ employees) as well as expanding relationships within existing accounts. You'll lead the entire sales process—from prospecting through negotiation and deal closure to nurturing and managing customer accounts—with the support of your very own Sailebot to help you identify, nurture, and qualify leads.

This role requires you to be a true AI evangelist—demonstrating how Sailes’ innovative solution drives substantial ROI and transforms how sales teams prospect, engage, and close.

Key Responsibilities:

Prospecting & Lead Generation: Identify and engage prospective customers through outbound strategies (cold calling, email campaigns, social selling) and follow up on inbound leads.

Discovery & Solution Selling: Conduct discovery calls to understand customer needs, challenges, and goals. Present tailored solutions that demonstrate the value of Sailes’ offerings.

Pipeline Management: Build and manage a robust sales pipeline to consistently meet or exceed monthly and quarterly quotas.

Closing Deals: Handle contract negotiations, address objections, and secure new business.

Account Management:

• Serve as the primary point of contact for assigned accounts, ensuring high levels of customer satisfaction and retention.
• Proactively monitor account health, provide ongoing support, and resolve any issues in collaboration with the customer success team.
• Identify upsell and cross-sell opportunities, presenting additional products or services that align with client needs.

Collaboration: Partner with internal teams, including marketing, product, and support, to enhance the customer journey and drive results.

CRM Management: Maintain accurate records of all sales activities, customer interactions, and account updates in [CRM tool, e.g., Salesforce, HubSpot].

Market Insights: Stay informed about industry trends, customer needs, and competitor offerings to position Sailes effectively.

Qualifications:

• Minimum 3-5 years of full-cycle selling experience, with a proven ability to sell complex, disruptive solutions to enterprise organizations.
• Experience in selling technology solutions—ideally AI, automation, or SaaS products.
• Ability to manage ambiguity and self-direct in a fast-paced, innovative sales environment.
• Exceptional communication skills—both written and verbal—with the ability to articulate the business value of abstract concepts like AI and Digital Labor™ in concrete, understandable terms.
• Proximity to NYC for weekly in-person collaboration.
• Influencer presence is a plus

This role is perfect for an ambitious sales professional with a passion for cutting-edge technology and a drive to help clients realize the transformative power of AI. If you’re ready to be at the forefront of sales innovation and help organizations revolutionize their sales processes, we want to hear from you.