Inside Summit: Fireside Chat with Kashish
To close out the Inside Summit, Madison and Claudia sat down with one of The Room Podcast’s early guests, CEO of Hightouch, Kashish Gupta. Listen to the conversation here on Apple and Spotify.
Gupta moved to the U.S. when he was just five years old. His father owned and ran a gas station in Atlanta, GA, which gave Gupta the hands-on learning that he never could access in school (though he did excel in school, graduating with an MSC in Robotics from Penn and a BS in Economics from Wharton). In his own words, watching his father handle everything from margins, to toplines, competition, and price advantaging taught him about being “a high agency person”. Overall, it was this real-world education that pushed Gupta to seek out environments where he could similarly learn from others, rather than books.
As a “chronic entrepreneur”, Gupta shared about his own persistence, and what drove him to reach early milestones as a YC participant.
Most important to that persistence?
A “why not me” mentality.
Though his first YC start-up was a travel-booking tool, Gupta has since pivoted to being the co-founder and CEO of Hightouch, which is a reverse ETL tool for syncing customer data from datawarehouses to business tooling. Hightouch is used by top-brands such as Petsmart, Spotify and Soundcloud.
Gupta is ⅓ of the founding team, which also includes his co-CEO Tejas Manohar and CTO Josh Curl. He shared about his experience as a co-CEO, and the advice he has for other teams considering the same model.
For Gupta, the “#1 thing you can do for your company is having a good relationship with your co founders”. He also stressed the importance of identifying skill and passion, and assigning tasks accordingly. After splitting verticals of marketing, GTM and product engineering, he and his team then identified where they needed help — either in the form of hiring or training.
As for what powers the co-ceo model, on the Hightouch team, each of the three leaders is driven by solving the “most important problem at that time”. For any team, figuring out the problems that each co-founder wants to solve is key to getting alignment and maximizing output.
Hightouch, which launched in July 2020, has seen impressive growth in the last few years. As Claudia called out, in 2022 the company was valued at $450M, and just two years later, is valued at $450M. Reflecting on this growth, Gupta recalled early strategies in GTM that helped get the company where they are today.
The first was figuring out what kind of growth was actually applicable. Early on in Hightouch, the team tried to retrofit a PLG GTM strategy, only to realize that when building for enterprise, sales and marketing are critical to the flywheel.
The other key point was identifying gaps and filling them creatively. Gupta and team acknowledged that they didn’t have a strong blog presence/following, so rather than try to establish that following, they hit the ground running by publishing blog posts on more trafficked channels (like Snowflake’s blog). As Gupta remarked, being “honest” about what strategies and tools they had and didn’t have allowed them to optimize early on.
As the company has grown and raised funding, Claudia and Madison asked Gupta for his advice on taking capital and creating a board.
On taking capital: “Do it when you have the most momentum”
On building a board: Gupta stressed the importance of learning and iterating before scaling. Keeping a small board has allowed Hightouch to be dynamic and scale effectively before bringing in more members. That said, Gupta echoed the sentiment of earlier guest, KJ Sidberry, who stressed the importance of transparency between a founding team and their board. Gupta took this one step forward, encouraging founders not to risk the trust of the board or employees by hiding problems, and instead, being honest and asking for help as soon as they arise.
To close the conversation, thoughts on generative AI, the future of Hightouch, and how he thinks the generation of founders has changed since he, Madison and Claudia entered the industry in 2018.
On Gen AI: Gupta first acknowledged that many marketers are “not ready” for the full automation of tasks that AI is promising. Rather, the innovation will come on the deep learning side to help marketers understand what the customer wants. Gupta and his team are looking forward to continuing to integrate with powerful generative AI models to change the future of marketing by customizing marketer experience.
On What He’s Excited About at HighTouch:
“Unlocking people and letting them run”
On How The New Generation of Founders:
“In SF, people are playing a positive sum game. Everyone wins”.
On how funders can best support founders?:
“Patience.”
For those who haven’t already, listen to Kashish’s first appearance on The Room Podcast in Season 7.
