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.
Company: Sailes
We are thrilled to have you join us today, welcome to ValiantCEO Magazine’s exclusive interview! Let’s start off with a little introduction. Tell our readers a bit about yourself and your company
Nick Smith: I’m the President, CEO and Founder of Sailes. I founded Sailes, Inc. after a long career in sales and sales leadership to be the first company to develop AI (Sailebots) that prospect autonomously on behalf of salespeople and account executives.
What specific areas of your business have been most impacted by AI, and how?
Nick Smith: Our Sailebot product is the nucleus of the company. It’s a wheel that drives the business internally and externally. It generates demand for our sales teams and our customers and there are numerous applications of AI throughout. Beyond the product, our engineering team uses AI in development and our Senior ML engineer uses AI in analysis. We even have AI ready to use on our website where we actually let customers compare us to competitors.
How are you ensuring ethical considerations are taken into account in your use of AI?
Nick Smith: Given our global enterprise customer base, it’s incredibly important that standards and international frameworks are followed. We use these in practice – some related to AI and some not – throughout the customer journey. An important note here is that we develop our models using our own primary data, which prevents some of the pitfalls from off the shelf models.
What advice would you give to other CEOs looking to integrate AI into their business?
Nick Smith: Start with a real problem and be obsessed with solving that beyond being obsessed with AI solving it. Sometimes AI is not the answer and the CEO may be tempted to apply it where it doesn’t make sense or to be influenced by eager voices internally that want to apply it. AI has changed the world forever and it can solve a lot of problems, but is it the best way to solve yours?
How do you see AI evolving in your industry over the next 5 years?
Nick Smith: Personally, I’ve felt the AI-as-task automation or the pervasiveness of companies that are AI in Name Only (AINO) to be disappointing. There are some great companies that provide task automation or work flows that lean heavily into AI marketing or branding. This creates a misnomer in the market that AI should be the 12th platform or 10th point solution in a stack. That’s not AI. AI is meant to fundamentally disrupt and improve lives. I believe AI should be replacing point solutions, replacing unnecessary workflows, and ultimately serve as a nucleus to the company. This is what we’re living with our company every day and hope that it can inspire others.


