Sailes builds personality-driven AI Sailebots to automate the entire prospecting lifecycle for the world’s leading sales executives and teams. Pulse 2.0 interviewed Sailes’ President, CEO, and founder Nick Smith to learn more about the company.
Nick Smith’s Background
Pulse 2.0 (Amit): Could you tell me more about your background?
Sailes (Nick): My name is Nick Smith, President, CEO, and Founder of Sailes – the company that created the first AI to automate all prospecting.
My journey with Sailes began in 2018, following a deep career in sales leadership with companies like CBS Corporation and iHeart Radio. Witnessing the transformative potential of AI in amplifying human capabilities, and noting the typical ‘sales enablement’ model in prospecting, I conceptualized the Sailebot. It was the first-of-its-kind invention that multiplied Sales Executives 16x. Rather than enable them to do more work, manually, it does all of the work for them – hands-free.
Our patent-pending Sailebot is not just another AI tool; it is the first and only AI designed to autonomously handle end-to-end sales prospecting and is currently in use by top-tier sales executives and teams across Fortune 1000 to 50 enterprises.
Formation Of Sailes
Pulse 2.0 (Amit): How did the idea for the company come together?
Sailes (Nick): I’ll be really specific. It was 11: 30 a.m. on July 4, 2018, and I was being yelled at by my family to hurry and get in the boat. We were at the Lake of the Ozarks and I needed a minute. I wrote down in my notes on my iPhone: Sailes. We actually ended up calling the business Saile for a while, but the first word was Sailes, which was pretty audacious but spelled with AI. I wrote down what I thought that would be, then I ran and got in the boat and it was on from that point.
We started with a problem before we started with AI. It wasn’t ‘What’s a cool AI company we could build.” It was very much a “Here’s a problem and I think AI can help us solve it better.”
I spent most of my career in sales and sales leadership. And the one constant throughout my career was the need to constantly be prospecting. Every Monday was like starting over or starting at zero. And so I learned firsthand that it was a problem companies not only had but were trying to solve in a number of different ways.
Next, I thought about myself as a sales executive; what would happen if I was starting a new job as a salesperson the next Monday? And I thought, ‘wow, there would be such an enormous amount of time spent ramping up just to get to the part that I’m good at.’ And I thought that it sounded miserable. And the idea literally was: what if I had my own bot to automate prospecting and just serve me more leads to close. Because I was a closer and I was a relationship builder and an expander… and that’s where my strength was. So if I had a personality-driven Sailebot, automating that upfront prospecting work and all of it, not just sending emails outbound, but everything from reading responses to finding the people to begin with, then I could be much more successful because I would constantly have opportunities served up. And then I took it a step further later down the road and thought, ‘What does this mean to their management? What does this mean to a sales manager?’ And there were a lot of problems to solve there as well. But that’s kind of how I narrowed in on it. And I will say I was pretty confident about product market fit from the beginning because, again, I did the job and I knew there was a need. But I also quickly learned that most, they call them sales enablement companies, most sales enablement companies are doing just that: They’re enabling more manual work. They’re not really doing the hard part, which in sales is creating demand, closing business, driving expansions, and so on.
I then got to work on the real-life solution to the age-old problem: I wish there were two of me.
Favorite Memory
Pulse 2.0 (Amit): What has been your favorite memory working for the company so far?
Sailes (Nick): My favorite memory working for the company so far has to be the day we turned on our go-to-market product for the first time. We had developed a Sailebot designed to prospect and engage potential customers, and it was a critical part of our strategy. I remember being at O’Hare airport in Chicago when we launched it, and witnessing someone respond positively to the Sailebot was a huge moment for me. Even though they didn’t end up becoming a customer, that initial positive interaction validated our efforts and demonstrated that the product worked. It was incredibly satisfying and reinforced my belief in our approach. This experience was pivotal as it marked the beginning of our growth, driven by these innovative Sailebots before we even had a dedicated sales team, which didn’t form until 2023.
Core Products
Pulse 2.0 (Amit): What are the company’s core products and features?
Sailes (Nick): Sailes has several core products, namely Sailebot, Digital Labor, and Starboard, each with distinct features aimed at enhancing sales efficiency and productivity.
As I mentioned earlier, Sailebot is an advanced AI system that automates the entire sales prospecting lifecycle. It significantly increases prospecting efficiency by 130% through the use of cutting-edge natural language comprehension and multiple AI models. With our version 2, which was released earlier this year, we’ve seen enhanced sales cognition, enabling it to perform complex tasks such as identifying referrals with the precision of a human sales executive. Additionally, it incorporates multi-layer intelligence, combining several AI models tailored to different steps in the sales process, which enhances its decision-making and reasoning capabilities. Best of all, as Sailebot learns and improves, it shares its intelligence with sales leaders, aiding them in refining their sales strategies.
Now a term I coined and then trademarked is Digital Labor. Digital Labor is essentially the sum of all the repetitive tasks that bog down SDRs daily which we automate, allowing sales execs to focus on high-value activities. By automating these tasks, Digital Labor significantly boosts productivity and can handle a large volume of tasks simultaneously, facilitating scalable outreach efforts without the need for additional staff. Moreover, Digital Labor improves conversion rates by using data insights to prioritize high-potential prospects.
The newest addition to our fleet of products is Starboard, released mid-2023. Starboard is the first CRM for AI that helps manage Sailebots for Captains as well as allowing users to onboard and train their fleet of Sailebots. Once onboarded, Sailers and Captains alike use our proprietary AI to create content and build targeted prospect lists, among a host of other customizations.
Challenges Faced
Pulse 2.0 (Amit): What challenges have Smith and the team faced while building the company?
Sailes (Nick): The challenge that happens at a startup is, soon enough, you’re having success and things get really busy. And as soon as that success comes, your space is invaded by people that have a difference of opinion… people that, maybe, are outside your walls but think they are inside the walls, and they want to share their opinion because they want the company to succeed as well. Or it’s your customers because they’re invested too. It’s then that you have to find a way to not lose any of that feedback while also keeping that space sacred for you, the founder that created this to begin with. So, what I’ve done when I know I have to brainstorm and I may or may not have the space to be creative is I record and talk to myself. A lot of Sailes was developed or ideated upon at the Lake of the Ozarks and the drive down, the time there, the drive back, there’s a lot of talking to myself and journaling.
Going back to feedback. Feedback can sometimes turn to pivoting, and pivoting is something that’s happening every single week at a startup. That is a benefit. It’s something that is an asset to a startup. It’s not a negative. Now, obviously, you don’t want things to be chaotic. But at a startup, you have the ability to continuously pivot and make small pivots along the way. I really believe that every week should be some sort of small pivot. I think that we, as a society, associate the word pivot with turning around, and giving up on something. It’s really just adjusting.
It’s making a move and adjusting for the market, for customer feedback, for internal feedback. And we’re doing that all the time.
My idea on prototyping, I’ll tell you, has changed after going through this experience. I think that there needs to be an environment of mutual understanding on iterations, on making progress, not making perfect. There needs to be a feedback loop and there needs to be an acceptance that we’re building and this will always get better.
That’s something that I could have embraced sooner to make us go even faster because, you know, newsflash, it’s never going to be perfect anyway, and it’s always going to change or update.
Evolution Of Sailes’ Technology
Pulse 2.0 (Amit): How has the company’s technology evolved since launching?
Sailes (Nick): We didn’t have a user interface until mid-2023, 5 years almost to the day that I wrote down ‘Sailes’ in my iPhone. Do you know what that means? That was 4+ years of customer success without the customer being able to visualize exactly what their Sailebots were doing. This was tough! But now looking back with rose colored glasses, we can be really proud of that, but it made it difficult.
Starboard launched as the first ever CRM for AI and is continuously optimized based on client feedback as well as investor suggestions. A couple of those I touched on previously but Digital Labor Live is a new addition that takes the visual of activities (Digital Labor) the Sailebot is doing and puts it right in front of the Captain so there’s no secret what the Sailebot is doing at any given moment. You can watch your AI work in real time. ROI Live is another addition to Starboard that helps Captains feel confident in their investment with their Sailebot.
I could talk about how Sailebot has evolved all day long. I mean, it evolves every single day, as it should. A stand out that comes to mind is that Sailebots now possess the unique ability to continuously learn and report back their findings to the owners. This dynamic capability keeps the Sailebot as an evolving tool that autonomously manages tasks while refining its performance based on real-world interactions. Acting as a digital extension of the sales team, the Sailebot leverages ongoing learning to adapt its strategies, aligning with the individual preferences and sales styles of each representative. This not only enhances efficiency but also fosters a deeper understanding of customer interactions, empowering the sales team to make data-driven decisions and achieve unprecedented success in the market.
Significant Milestones
Pulse 2.0 (Amit): What have been some of Sailes’ most significant milestones?
Sailes (Nick): There have definitely been some big ones. For starters, we’ve reached a remarkable 130% year-over-year growth and adoption by Fortune 500 to Fortune 50 companies. Additionally, our client roster boasts prominent names such as Staples, Wiley, and Rogers Electric and Sailebots are now operational in 25 countries and support multiple languages, including German, French, Spanish, Italian, and English.
Furthermore, Sailes was selected as one of 10 companies for the Comcast NBCUniversal LIFT Labs Enterprise AI Accelerator, a program designed to hand select innovative startups to work onsite with specific divisions of Comcast.
Total Addressable Market
Pulse 2.0 (Amit): What total addressable market (TAM) size is the company pursuing?
Sailes (Nick): The total addressable market (TAM) Sailes is pursuing is $25.3 billion, encompassing approximately 351,520 large companies.
Differentiation From The Competition
Pulse 2.0 (Amit): What differentiates Sailes from its competition?
Sailes (Nick): What sets Sailebot apart is its role as a personal AI companion for enterprise sales executives, operating seamlessly to navigate the complexities of the sales process. It’s crucial to emphasize that we don’t merely offer a platform with AI capabilities; we provide a transformative experience with a technology that mirrors the nuanced approach of human sales executives. Sailebot goes beyond the conventional understanding of AI, learning the intricacies of an ICP and engaging customers with a level of sophistication that mirrors human interaction.
One of Sailebot’s key advantages is its continuous learning capability. It gets smarter over time, adapting to new information and improving its responses. The autonomy of Sailebot is a game-changer, reading and reacting to responses, thus freeing up valuable time for sales leaders to focus on strategic decision-making rather than mundane tasks.
Our commitment to hands-free, autonomous sales prospecting is not just a claim but a tangible reality. Our AI technology actively contributes to revenue generation by delivering real opportunities back to sales leaders. This level of integration and effectiveness is a testament to our dedication to pushing the boundaries of what AI can achieve in the realm of enterprise sales. As we continue on this journey, we remain steadfast in our pursuit of excellence, consistently refining and advancing Sailebot to meet the evolving needs of the sales landscape.
Future Company Goals
Pulse 2.0 (Amit): What are some of the company’s future company goals? Smith concluded:
Sailes (Nick): Our future goals for 2024 focus on positioning our AI as a leader in sales automation applications and setting new industry standards. We aim to not only participate in the market but to drive innovation, shaping the future of sales with our advanced AI solutions. A key aspect of this success involves expanding our AI’s capabilities beyond traditional automation.
We are working towards enabling our AI to process visual data with exceptional accuracy and to adapt and learn dynamically in real-time situations.
A cornerstone of our vision is Starboard, our dashboard that facilitates interaction and collaboration between our AI and human Sales Leaders, Captains and Sailers. This year, we envision Starboard evolving into a dynamic environment where AI and human expertise seamlessly integrate. It will be more than just an automation tool; it will be a collaborative space where our AI benefits from the insights of human Sales Leaders, and vice versa. Our goal is to create a symbiotic relationship, fostering a continuous exchange of knowledge and performance trends that elevate both AI and human contributions to new levels of excellence.
