Closing the Deal: Turn Insights into Action with the Help of AI


Companies face significant hurdles if they don’t have a strong data foundation. SetSail grew from a need to address a major challenge shared by many large enterprises: how to get clean data and turn it into actionable insights for sales and go-to-market teams.

In this era of virtual and distributed work, sales reps and managers are essentially flying blind if they don’t have an accurate view into their customer accounts or pipelines. When sales leaders want to coach their teams, they fall back on anecdotes, their own experience, and word of mouth, because they have no data on which to base their advice. 

There are also a lot of silos between departments, which lead to inefficiencies. Many companies have multiple incomplete databases where they store their customer information. A lot of time is wasted trying to keep those databases in sync and discover the ultimate source of truth. This reduces everyone’s ability to identify and execute opportunities, and it makes for a bumpy transition when a client moves from one rep to another, or from the sales team to the customer success team. 

When a customer transition process is manual, significant customer information can be lost. Who are the key people involved? What is their primary use case and the challenge to be solved? This leads to a less-than-ideal experience for customers. 

While working at Google, Haggai Levi and I came up with a unique approach to these issues that combines machine learning and behavioral science. After trying this approach in a few different areas within Google and finding it to be very effective, we brought it into the world as SetSail in 2018. Today, SetSail employs 30 people. Haggai is the CEO and I am the Chief Product Officer.

Beyond Insights to Action

A lot of companies who use AI in sales right now have fallen short by stopping at insights. Our initial vision for SetSail was to turn data into action by leading our customers to the actual activities that seal a deal. That goal hasn’t changed, but what we realized since we founded SetSail is that many of our customers need to start at the foundational level of getting the basics of data right. So, while we still turn insights into action, that is the final step in a three-step process. 

Step one is to capture all the data in one place, make sure it’s clean, and make sure it’s accessible. All this happens in the background, so there isn’t any additional administrative work. It takes place through integrations with the channels where sales reps engage with their customers, such as Outlook or Salesforce. We then use orchestration logic to map out all of a seller’s engagements and contacts with customers, and record that within their CRM. We then enrich that data with information on the contact’s job title and workplace.  

Once you build a strong data foundation, you have to look at the data to discover what works.

Now that we have this data foundation, step two is looking to the data to discover what works. If we’re talking about a deal cycle, how do we know why deals are won or lost? This is where we use machine learning to measure different buying signals to determine the milestones and key behaviors that move a deal forward. This is one of our major points of emphasis, and what sets us apart from the typical approach that examines vanity metrics. 

It’s not about the quantity of activities—the number of meetings you have, the number of emails you send, the number of phone calls you log. Working from our buying signal library allows companies to hone in on what really matters, which is the quality of the interaction. If you’re meeting with a client, are you speaking with a high-level decision maker? The product you’re talking about, is it a pilot or a beta? We can extract these kinds of buying signals with our machine learning, and identify the buying signals that matter most to a particular company. 

The third step is to translate all of this into action: going beyond a dashboard with insights to creating an engaging and rewarding experience for salespeople. Up to this point, everything we do has been going on in the background, with no interruption to the seller. At this stage, we surface those insights and give visibility to reps and sales leaders on the progress of their teams when it comes to these different buying signals. We also give them the ability to run fun and engaging competitions to boost their team’s performance.

Empowering people to do better is what drives us. It’s why we founded this company and is what keeps us excited every day. We’ve found, however, that we have to teach many of our clients to walk in this direction before we can run with them. 

Our Unique Partnership with Cisco Venture Labs

In early 2020, we began conversations with Cisco Venture Labs, a new division of Cisco that partners with leading analytics and AI startups to solve key business challenges. We realized almost from the start that there was a lot of alignment between our efforts to help customers build a data foundation and translate that into action, and how Cisco wanted to improve their own engagement with customers.

A lot of those challenges we noticed at Google and with other enterprise companies were shared by Cisco across their teams. CRM data quality is a recurring issue, and they also realized that better sales data would bring value across their organization, from forecasting and cross-selling to territory coverage and coaching. From those early conversations we developed a pilot to demonstrate how SetSail could solve these issues and create that added value. Two countries within Cisco’s international portfolio, Canada and Germany, jumped at the opportunity to work with us, so that’s where we started.  

Better sales data brings value across an organization, from forecasting and cross-selling to territory coverage and coaching.

With this sort of project, we obviously worked with the Cisco technical teams to get the technology up and running, but we also worked closely and hosted live feedback sessions with the users, showing them the data and intelligence SetSail can provide. That was one of the most exciting aspects of the pilot for me, because I love talking to customers, whether it’s the executive buyers or the end users. 

When we work to get buy-in from sales reps, one of the things we emphasize is that everything we do happens in the background of their normal activities. It was so rewarding, then, to hear someone say, “This is like magic,” because they have so much more information available without any additional work. In those live sessions, I also heard that it used to be a difficult process to pass a customer from one rep to another when territories changed. With SetSail, it’s easy to pass the torch and know from day one who’s who in your new account. Finally, after Cisco validated the accuracy of sales data with sellers, we heard that the contact information was extremely accurate.

Cisco found SetSail to be responsive to feedback and the discovery of complex data structures, as well as easily customizable within Cisco’s existing environment.

Learning From One Another

After the pilot in the summer of 2020, we began to move toward a widespread rollout to 90 countries across Cisco in January 2021. Teams have never had this type of data available to them before, and the sheer number of possible use cases can be overwhelming. That’s why, at least to start, we advised teams to focus on one or two use cases that have the greatest impact and the quickest to add value. 

Speed is of the essence throughout this project. Not only has SetSail gone from zero to 90 countries in many languages and roles at Cisco in a matter of months, but we also enable Cisco to move quicker. We know how long it can take to onboard a new sales rep and see them start driving revenue. SetSail empowers them to be ready from day one. As for the speed of our implementation, we just hit the milestone of identifying 125,000 new customer contacts. 

When adopting a new solution, the number of possible use cases can be overwhelming. Focus on one or two with the greatest impact and shortest time to value.

As we build this data foundation globally across Cisco, we’re also focused on partnering with the Cisco data science and analytics teams on all the ways they could use this data. By doing so, we will further explore how the data SetSail provides could fuel Cisco’s larger vision. 

There are a lot of upsides to working with a company like Cisco, one of them being the scale at which they operate. They have so much experience scaling up and managing the complexity that goes along with that. Partnering with Cisco Venture Labs, we’ve had the opportunity to learn so much in this regard. 

SetSail and Cisco are both aware we’ve just scratched the surface of opportunities, and I know Cisco’s data science team is as excited to be working with us as we are with them. We are helping Cisco find all the ways to get the most out of their customer contact data, and Cisco, in turn, is teaching us ways we can further refine our product for the benefit of all our customers.