Head of Sales

About Sailes:

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.

Our Sailebots are not just sales enablement agents but a true Digital Labor solution that multiplies the power of world-class AEs by 16X.

At Sailes, we’re scaling the future of sales, and we’re looking for a visionary Head of Sales to lead our team of high-performing Account Executives to new heights of excellence and growth.

Your Mission:

As the Head of Sales, you will spearhead the growth of Sailes’ revenue engine, driving strategy, execution, and results across the entire sales organization. You’ll build and scale a dynamic, high-performance sales team while ensuring we meet and exceed ambitious revenue goals. Reporting directly to the leadership team, you’ll act as a key stakeholder in shaping our go-to-market strategy and customer success initiatives.

Key Responsibilities:

Strategic Leadership:

• Design and implement a modern GTM sales process, playbooks, benchmarks, and associated reporting
• Define sales goals, establish KPIs, and lead the team to consistently achieve and exceed targets.
• Collaborate with leadership on go-to-market strategies, pricing, and product positioning.

Team Management:

• Recruit, train, and mentor a team of Full Cycle Account Executives and other sales professionals, ensuring continuous development and engagement.
• Foster a collaborative and results-driven culture, promoting accountability and excellence at every level.
• Provide coaching on prospecting, solution selling, pipeline management, and closing strategies.

Revenue Generation:

• Drive the end-to-end sales process, from lead generation to contract negotiations and renewals.
• Oversee strategic account planning and ensure top-tier account management practices across the team.
• Proactively identify growth opportunities, both with new prospects and existing customers, to increase recurring revenue.

Customer Engagement:

• Cultivate relationships with key clients and act as an escalation point for high-value accounts.
• Partner with the support team ensure a seamless onboarding experience and high levels of customer satisfaction and retention.

Data-Driven Decision Making:

• Utilize data insights to refine strategies, optimize workflows, and drive operational efficiency.
• Ensure accurate forecasting, reporting, and CRM management across the sales organization.

Market Insights:

• Stay ahead of industry trends, competitive movements, and emerging technologies to maintain Sailes’ leadership position in the market.
• Share feedback with product and marketing teams to influence roadmaps and campaigns.

Competencies:

• 7+ years of progressive experience in sales, including leadership roles, with a proven track record of scaling teams and driving revenue growth.
• Deep expertise in full-cycle sales, including prospecting, closing, and account management.
• Strong analytical skills with the ability to turn data into actionable insights.
• Exceptional communication and negotiation skills, with a talent for influencing stakeholders at all levels.
• Proficiency in using sales tools (e.g., Salesforce, HubSpot, Gong) and a data-driven approach to managing pipelines and forecasting.
• Experience in SaaS, technology, or B2B industries is strongly preferred.
• Thrives in a fast-paced, entrepreneurial environment with a hands-on leadership style.
• Bachelor’s degree in Business, Marketing, or a related field; MBA is a plus.