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Nick Smith

Founder & CEO at Sailes
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Nick Smith is the President, CEO, and Founder of Sailes – the company that created the first AI software to automate all prospecting. Nick founded Sailes in 2018 after an extensive career in sales leadership at CBS Corporation, iHeart Radio, and other enterprise sales organizations. Recognizing the power of AI to multiply human potential, and with the knowledge that most sales teams were taking a proportional, “sales enablement” approach to prospecting, Nick invented the Sailebot® to prospect on behalf of Sales Executives while accounting for their unique personalities.

Nick’s accolades include an Eagle Scout award, a two-time CBS New York “One to Watch” award, and being named “40 Future Leaders of New York Politics” by City and State Magazine. Prior to founding Sailes, he co-hosted “Common Ground,” an audio program on WOR New York and iHeart Radio, dedicated to building bridges between business and labor organizations.

Sailes, a venture-backed “Startup to Watch”, currently serves Fortune 1000 to 50 enterprises and is based in New York, NY and Kansas City, MO.

Employment
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  • Nick Smith's Sales Strategy: Connect, Learn, Succeed
    Nick Smith, CEO of Sailes, advises new sales reps: Prioritize genuine connections, use technology smartly, and continuously learn. His humble beginnings in a smoky Camry led to mastering sales through storytelling and relationship-building.
  • Sailes CEO Projects AI-Driven Hiring Boom
    Nick Smith, CEO of Sailes, expects a summer hiring spike, with a 200% applicant increase for AI roles. Sailes leverages internships to test new positions and uses local events and unique branding to attract top talent.
Recent Quotes
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  • "Balancing competition and collaboration is an art in sales. While healthy competition can drive individual excellence, collaboration fosters a team spirit. I’ve found that setting team goals alongside individual targets can strike this balance effectively. For example, when we instituted a Digital Labor™ sales competition, it resulted in remarkable performance improvements. The collaborative aspect pushed team members to help each other succeed, which ultimately benefited the entire team."

  • "A great sales team is built on a foundation of trust, collaboration, and a shared commitment to success. I believe in cultivating a culture of continuous improvement, where team members are encouraged to enhance their skills and adapt to evolving market conditions. Effective communication, adaptability, and a customer-centric approach are crucial strengths I aim to cultivate within my team."

  • "In my career, the most interesting story revolves around the inception of Sailes. It all began on July 4th, 2018, at the Lake of the Ozarks in Missouri. I had a moment of inspiration that salespeople should have their own AI Sales Robot “Sailebot” that could automate prospecting tasks, allowing them to focus more on selling. I vividly remember jotting down this idea in my phone. The lesson I took from this is that great ideas can strike at any moment, even on a holiday, and it’s essential to act on them. Sometimes, those ideas can lead to transformative innovations."

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