As SetSail's VP of Design, I led the design of an AI-powered analyst that empowers revenue teams to sell smarter.

 Roles

    • VP of Design
    • SetSail Cruise Director 

Responsibilities

    • Collaborate with the CPO to define the product vision, strategy, & OKR's
    • Optimize the design-to-development workflow with the CTO & push the limits of feasibility in order to maximize customer value
    • Partner with the CMO to define a bold PLG strategy to drive self-serve user adoption & viral user growth
    • Foster company-wide cross-functional collaboration
    • Co-create (as Cruise Director) a company-wide culture of inclusion 

Results

    • Led the research-based design & iteration of an AI-powered revenue analyst that generated strong engagement in early trials with customers & design partners 
    • Designed an AI-powered notification system that achieved a customer open rate >80% 
    • Led the design of a React-based design system that enhanced UI coherence & reduced development time by >50% 

SetSail AI

 

SetSail began with a singular vision: to harness the power of sales data to drive revenue growth. This data could only be effective for GTM teams if it was complete, current, and omission-free. Therefore, the founding team created a platform that collected all essential types of sales data relating to reps, opportunities, and accounts – including emails, calendar events, meeting recordings, performance metrics, and additional key info – and wrote it all to the customer’s CRM. Tools were then built upon this data foundation that enabled sales leaders to identify and incentivize the most effective behaviors of their reps. This became known as SetSail’s Sales Data Platform.

 

The Problem

 

Even the best, most complete data platforms don’t hit revenue targets – high-performing sales reps do. While data completeness certainly helps, if reps don’t know how to decipher and skillfully use this data, it doesn’t move the needle. What sales leaders truly needed was for every rep on their team to have easy access to the data and insights that would help each of them rock their meetings and crush their targets.

 

 

 

The Solution

 

Enter the transformative power of AI. Built on the foundation of the Sales Data Platform and surfacing as customizable push notifications, SetSail AI delivers the precise info, when & where sales reps need it, to help them track & close more deals.

When reps want to dig deeper into any notification, SetSail AI makes this easy with contextually-relevant suggestions and the ability to ask anything directly to their enterprise sales data. 

 


Our Process

 

Ideation

Listen & learn from customers

 

Shortly after the launch of Open AI's ChatGPT API in November of 2022, we realized that it radically transformed the technology landscape. By enabling people without coding skills to interact with enormous sets of unstructured data as easily as if they were having a chat with a coworker, GPT unlocked data analysis superpowers for all. 

 

Without needing to write a single line of code, people could use natural language to ask in-depth questions directly to their enterprise data. What was once a laborious and expensive process that required data analysts to write sophisticated custom queries in order to extract insights from enterprise data lakes had been transformed into a quick and casual interaction. This enabled people to make sophisticated data-driven decisions at a greater speed and with vastly less effort and cost than had previously been possible. 

 

Recognizing how this disruptive new technology was set to transform the revenue intelligence space, we treated the launch of GPT as the starting signal in a race to get these powers in the hands of our customers as quickly as possible. Although the race was on, we prioritized a factor even more highly than speed to market: Speed to impact.

Our true measure of success wasn’t how quickly we could graft AI onto our product and rush it into our customers’ hands; it was how effectively we could deliver the precise features that would create a step change in the efficiency and effectiveness of their work.

Maximizing our speed to impact demanded a rigorous process of engaging deeply and frequently with our customers & design partners. We conducted in-depth interviews to assess their highest-priority needs, to understand their concerns about using generative AI, and to map their ideal workflows. Upon analyzing these findings, our team developed hypotheses about the most valuable solutions to their needs and tested them in follow-up sessions. We then rapidly designed functional prototypes, tested these prototypes, iterated the designs based on our findings, and then tested them again with our customers.

Throughout the early ideation and testing phase, our Product team maintained tight coordination with our Data Science and Engineering teams, providing the guidance they required to build the scaffolding required for our reinvented product. We also collaborated closely with our GTM teams, learning from our Sales team members about market interest and demand and partnering with Marketing to co-create a PLG strategy that would drive self-serve adoption and viral user growth.

An Early Correction

The chat-based design pattern of ChatGPT had led us to believe that sales reps would primarily want to use AI to  “Ask anything” of their sales data. However, early testing of this hypothesis wotj customers revealed that rather than requiring users to pull information from a system by formulating and asking questions (which required a significant amount of mental effort), most users preferred a system that would automatically push to them the information they wanted, how and when they wanted it. 

This pivotal early research finding gave rise to SetSail AI’s primary feature – Notifications.

 

SetSail AI – Early User Flow Diagram 

 

We used this insight to redesign the user flow, moving the Notifications flow into primary position and the "Ask Anything" flow into secondary position.

Positioned between these two main flows, the Settings flow enabled users to  configure SetSail AI to their liking.

Now that our research had revealed that users prefer to receive notifications over asking anything, the key question became: Which notifications? 

 

Prototype & test

 

As soon as our research with customers validated that we had discovered the kind of interaction that would be most valuable to sales reps – push vs. pull – we focused on learning their preferred types of notifications and the content that would be most useful for them. 

Sales reps ranked their preferred notification types accordingly: 

      1. Email (~75%)
      2. Slack (~23%)
      3. In-app (~2%)

Regarding content, our research showed that reps considered these notifications most useful: 

      1. Meeting Prep – "Give me all the info I need to rock my sales meetings."
      2. Accounts at Risk – "Which accounts are at risk of churning and why?"
      3. Opportunities at Risk – "Which deals looks like they might not close and why?"  
      4. Pipeline Generation – "Provide an overview of key stats, e.g., new opportunities created, new business meetings booked  
      5. Anomaly Detection – "Alert me when circumstances deviate from the norm (both in ways that appear negative & positive)."  
      6. Weekly Recap – Provide an overview of the key events of this past week

Here's an example of an email notification that we designed, tested, and iterated based on customer feedback:

 
 


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I'm making daily additions and edits. Check back soon for a more complete version... 

 

SetSail Team Feedback

"Shalom  is a passionate and skillful partner and leader, always inspiring our team to do our best work and pushing our product to deliver on its highest potential and delight our users.

"Beyond his design expertise, he excels at collaboration and user empathy. Shalom fostered communication between design, marketing, sales, and customer success. He created a tight feedback loop and ensured our product vision was clear and aligned across the company.

"More than any designer I've worked with, Shalom has a passionate focus on the human dimension of human-centered design. He's constantly (one could say obsessively) striving to understand our customers and to solve their problems in the most useful way. And, he rigorously tests and iterates his work based on feedback. This philosophy proved instrumental when he tackled the challenge of integrating AI features into our product. He worked tirelessly to "humanize AI", with early testing showing great success..."

- Bert Lui, CPO

"Shalom has been an exceptional VP of Design at SetSail for the past two years. His leadership in cross-functional team collaboration has been transformative, consistently building bridges between teams and fostering a culture of cooperation and shared vision. His devotion to human-centered design is truly inspiring; he approached every challenge with deep empathy for our users, ensuring that their needs and experiences are at the forefront of every decision.

"Shalom never settles for simply useful solutions but continuously pushes our products to realize their fullest potential, always striving to delight our users."

- Haggai Levi, CEO

 

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