Position: President, CEO, and Founder
LinkedIn: [linkedin.com/in/nixmith](http://www.linkedin.com/in/nixmith)
Executive Summary
Nick Smith is the President, CEO, and Founder of Sailes, an enterprise AI company specializing in automating the entire sales prospecting lifecycle. Since founding Sailes in 2018, he has pioneered the development of Sailebot, the first AI designed to autonomously execute hands-free sales prospecting for large enterprises and leading sales organizations globally. Under Nick's leadership, Sailes has experienced over 130% year-over-year growth, rapidly expanding its client base across Fortune 500 to Fortune 50 companies and deploying AI solutions in 25+ countries.
Professional Background
Nick Smith brings a deep background in sales leadership from prominent organizations including CBS Corporation, iHeart Radio, and Audacy. His career trajectory is marked by strategic roles in enterprise sales management, political advertising, and abstract selling, providing him substantial insight into the operational pain points of large sales organizations.
- Founder of Sailes (2018–Present): Nick established Sailes to solve the fundamental issue of manual prospecting. Drawing on his frontline experience, he designed Sailebot, a software platform utilizing natural language understanding and multi-model AI to automate tasks typically performed by sales executive teams.
- Developed the Sailebot technology, multiplying sales executive productivity (claimed up to 16x), and promoted a vision of "digital labor"—automating the repetitive tasks of sales development representatives (SDRs).
- Sales Leadership (Prior Experience): Before Sailes, Smith led strategic and high-velocity sales teams at major media companies, where he was twice awarded the CBS New York “One to Watch” and was named one of the “40 Future Leaders of New York Politics” by City and State. He is also an Eagle Scout, highlighting his dedication and leadership from a young age.
Key Achievements & Industry Recognition
- Founded Sailes in 2018 with a problem-led, innovation-driven approach.
- Sailebot became the first AI system to autonomously handle end-to-end sales prospecting, now in active use across Fortune 1000 and Fortune 50 organizations.
- 130% YoY growth in revenue and client adoption.
- Multi-national reach: Sailebots are live in 25+ countries, supporting a wide range of languages (English, German, French, Spanish, Italian).
- Major clients include: Staples, Wiley, Rogers Electric, among others.
- Selected as one of 10 companies for the prestigious Comcast NBCUniversal LIFT Labs Enterprise AI Accelerator in 2023.
- Product and thought leadership featured in leading business publications including Forbes, Entrepreneur, and Pulse 2.0.
- Developed and trademarked the concept of “Digital Labor”—scalable, AI-driven automation of SDR tasks, which delivers significant productivity gains and conversion lift for sales teams.
- Contributes as a member of the Forbes Technology Council and is recognized as a market leader in AI automation for sales.
Sailes – Company Profile
Founded: 2018
Core Offerings:
- Sailebot: An AI-driven system capable of fully automating the sales prospecting lifecycle (identifying leads, engaging, qualifying, and reporting).
- Version 2 (2024 release) includes multi-layer AI cognition, contextual referral identification, and enhanced learning algorithms.
- Digital Labor: Trademarked concept referring to the automation of repetitive sales development tasks, enabling sales teams to focus on high-value, relationship-driven work.
- Starboard: Launched mid-2023, the first AI-centric CRM for managing, onboarding, and training Sailebots—designed for both “Captains” and frontline sellers.
- Digital Labor Live: Visualizes all ongoing AI activities for sales leaders in real time.
- ROI Live: Provides transparency and analytics on conversion and performance.
Market Positioning:
- Pursuing a $25.3B total addressable market with a focus on 351,520+ large enterprises.
- Differentiates by providing truly autonomous, "hands-free" prospecting AI as opposed to enabling more manual labor.
- Focused on hyper-personalization, dynamic learning, and seamless AI-human collaboration, integrated with enterprise sales ecosystems.
Noteworthy Milestones:
- Enterprise client expansion: Rapid early-stage adoption before even forming a dedicated sales team (sales team organically established in 2023).
- Consistent innovation cycles: Fast prototyping, customer-driven iteration ("small pivots"), and UI additions, especially Starboard, built from direct enterprise feedback.
Leadership Philosophy & Vision
Nick Smith emphasizes:
- Continuous innovation—driven by both client and investor feedback, with agile product pivots on a weekly basis.
- Mutual learning between AI and sales executives—creating an ecosystem where AI capabilities are shaped by real-world feedback.
- Empowering sales talent—allowing human executives to focus on closing and relationship management while AI handles scaling and qualification work.
- Commitment to go beyond traditional sales enablement, firmly positioning Sailes as a transformative solution provider in the enterprise sales tech sector.
Future Roadmap (2024–2025):
- Enhance AI’s multi-modal capabilities (e.g., advanced visual data processing).
- Evolve Starboard into a true collaborative workspace between human and AI, maximizing the exchange of actionable sales intelligence.
- Set new industry benchmarks for AI-driven sales automation, aiming for deep integration within global enterprise sales infrastructures.
Professional Accolades & Community Involvement
- Eagle Scout (leadership and service distinction)
- CBS New York “One to Watch” recipient
- Named “40 Future Leaders of New York Politics” by City and State
- Frequent speaker and panelist at AI, sales technology, and enterprise innovation conferences
- Published author and cited expert in the fields of AI, digital sales, and productivity automation
Education
- Attended the University of Missouri-Columbia (details of degree not specified in sourced information)
Geographic & Operational Footprint
- Based in New York, NY
- Sales, engineering, and client success operations supporting a global clientele, with product scalability demonstrated through active deployments in North America, Europe, and beyond.
Insights for Business Engagement
Nick Smith brings deep enterprise sales leadership, hands-on product innovation, and AI expertise to every partnership. His proven ability to identify core prospecting challenges, validate business needs, and rapidly iterate product offerings positions Sailes as both a technology vendor and a strategic partner to global sales leaders. Organizations engaging with Sailes can expect accelerated sales pipeline volume, enhanced qualification processes, and cutting-edge automation practices under Smith’s leadership. His personal visibility and thought leadership within the AI and enterprise technology sectors reinforce Sailes’ reputation as a high-trust, innovation-driven company for large-scale sales transformation initiatives.
