AI Account Executive

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 report directly to the CEO and 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 to negotiation and deal closure—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 include:

• Conduct Discovery Calls: Understand business challenges and strategic initiatives, positioning Sailes’ AI-driven solution as the key to solving pain points and driving measurable outcomes.
• Tailor Solutions: Showcase how Sailes’ AI technology delivers personalized, scalable solutions that meet a prospect’s most important business objectives.
• Collaborate & Innovate: Work with peers, sales leadership, and product teams to continuously improve Sailes’ offerings and the way you sell them. Share best practices and contribute to developing the future of sales AI.
• Lead the Sales Cycle: Navigate complex sales cycles with contract values ranging from five to high-six figures. Use your AI-powered prospecting tools to streamline lead generation, qualification, and deal progression.
• Expand Customer Accounts: Post-sale, continue to work with the customer success team to expand relationships and ensure that clients realize the full value of Sailes' AI capabilities.
• Achieve Sales Targets: Consistently exceed revenue and pipeline goals by strategically selling AI-powered solutions that transform prospecting and sales workflows.

Competencies:

To thrive in this role, you will need to possess a blend of technical understanding and sales acumen, along with the ability to build strong relationships with senior decision-makers in medium-to-large organizations.

• AI Sales Expertise: A deep understanding of AI technologies and how they are transforming the sales landscape.
• Consultative Sales: Ability to engage prospects in meaningful conversations, uncover their needs, and position Sailes' AI-driven solution as a strategic asset.
• Sales Strategy: Navigate long sales cycles (3–9 months) and manage complex, multi-stakeholder deals with contract values starting in the five-figure range and scaling upwards.
• Strong Negotiation Skills: Proven experience in structuring and negotiating high-value contracts.
• Relationship Building: Develop trusted partnerships with prospects and customers, driving long-term loyalty and expansion.

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 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.

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 report directly to the CEO and 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 to negotiation and deal closure—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 include:

• Conduct Discovery Calls: Understand business challenges and strategic initiatives, positioning Sailes’ AI-driven solution as the key to solving pain points and driving measurable outcomes.
• Tailor Solutions: Showcase how Sailes’ AI technology delivers personalized, scalable solutions that meet a prospect’s most important business objectives.
• Collaborate & Innovate: Work with peers, sales leadership, and product teams to continuously improve Sailes’ offerings and the way you sell them. Share best practices and contribute to developing the future of sales AI.
• Lead the Sales Cycle: Navigate complex sales cycles with contract values ranging from five to high-six figures. Use your AI-powered prospecting tools to streamline lead generation, qualification, and deal progression.
• Expand Customer Accounts: Post-sale, continue to work with the customer success team to expand relationships and ensure that clients realize the full value of Sailes' AI capabilities.
• Achieve Sales Targets: Consistently exceed revenue and pipeline goals by strategically selling AI-powered solutions that transform prospecting and sales workflows.

Competencies:

To thrive in this role, you will need to possess a blend of technical understanding and sales acumen, along with the ability to build strong relationships with senior decision-makers in medium-to-large organizations.

• AI Sales Expertise: A deep understanding of AI technologies and how they are transforming the sales landscape.
• Consultative Sales: Ability to engage prospects in meaningful conversations, uncover their needs, and position Sailes' AI-driven solution as a strategic asset.
• Sales Strategy: Navigate long sales cycles (3–9 months) and manage complex, multi-stakeholder deals with contract values starting in the five-figure range and scaling upwards.
• Strong Negotiation Skills: Proven experience in structuring and negotiating high-value contracts.
• Relationship Building: Develop trusted partnerships with prospects and customers, driving long-term loyalty and expansion.

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 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.