The $1.2 Billion Pivot: Kashish Gupta’s Journey is the Quintessential American Dream
From his father's gas station in India, to building a $1.2 billion data platform, one founder's journey shows why betting on pivots—and people—changes everything.
Written by: Brianne Garrett Original photography by: Irina Logra and Olga Moiseenko
The Five-Year-Old's American Dream
For Kashish Gupta, fuel for thought came early. At five-years-old, he left his home in Haryana, India — four hours north of Delhi — for Atlanta, where his father staked everything on running a gas station in the Peach State. It was an early crash course in resilience and hustle that Gupta would come to appreciate, and rely on.
Gupta would need it for an entrepreneurial journey marked by relentless pivots, including a major shift during the global pandemic. Rather than let shifts derail his dream, each twist strengthened Hightouch. The company, valued at $1.2 billion, is now transforming how the world’s biggest brands — including Calendly, PetSmart, Warner Music, and Cars.com — use data and AI to deliver personalized marketing and forge deeper connections with customers.
The Gas Station MBA: Early Lessons in Building a Business
The gas station was undoubtedly Gupta’s first business classroom. Watching his father juggle priorities like margins, wholesaling, and accounting — grinding to keep a business in a competitive market alive and his family supported — taught Gupta lessons no traditional curriculum could match.
An early business lesson gleaned from his dad was, “Business is something you can’t learn in school. You have to learn on the job.” It helped that Gupta would also go on to study economics and computer science at Wharton and, later, continue on at UPenn to earn his Masters in machine learning.
Kashish, Josh, and Tejas.
This 360-degree lens, combining the out-of-the-box thinking from his dad with foundational business education, proved useful for Gupta in many ways. For one: It helped position Hightouch to disrupt the customer data sector at a time when major players, including Segment, where his two co-founders Tejas Manohar and Josh Curl worked before founding Hightouch, were already dominating the market.
Largely thanks to customer feedback (more on this later), Hightouch stepped in to serve businesses what they were missing: an architecture that would allow them to collect and leverage customer data from their own existing data infrastructure, rather than rely on traditional CDPs (Customer Data Platforms), which operate separate from the internal data warehouses of companies. This innovative approach, offering companies greater flexibility, control, and security, helped spark what’s now widely referred to as “composable CPD.”
Second, Gupta resisted the temptation to focus only on Silicon Valley’s biggest players. By design, Hightouch’s customers are remarkably diverse, ranging from companies in healthcare, DTC retailers, B2B SaaS startups, and Fortune 100 enterprises.
“We are mostly opportunity-seeking rather than risk-mitigating,” says Gupta, a mentality deeply rooted in watching his father’s courageous leap into immigrant entrepreneurship, and one that continues to serve him well. “Companies don’t die because of anything else other than giving up. If you can stay the course — building a new product on top of an existing one, raising more money to beat competitors, whatever it means — eventually things will probably work.”
The Power of the Pivot: From Travel Bots to Billion-Dollar Valuation
Hightouch hit snags before it hit big. Long before Gen AI was mainstream, Kashish described Hightouch as essentially like a “ChatGPT for travel” — a Slack-bot travel-booking service. Then in 2020, COVID happened, sparking a dire need to pivot (a blessing in disguise retrospectively, given the travel sector’s low margins and high competition).
With his co-founders on board, fresh out of their roles at Segment, the trio transitioned a few more times, pivoting to customer communications, then customer dashboards, and eventually to what they’re doing today: “the actual orchestration layer for customer data,” says Gupta.
Working on Hightouch’s side was its loyal customers — 30 of which changed everything. To identify a bold pivot, it interviewed a diverse set of B2B and B2C brands that shared a common pain point: not knowing that their customers actually wanted to buy.
“I don't think we could say truthfully that this was an idea that we had on a whiteboard,” adds Gupta, but it was the true lightbulb moment. “It was hearing many diverse customers say the exact same thing, which is that they're centralizing their data, and they don't have a way to make marketers self-serve. Oftentimes, your customers will tell you truths that you're not ready to hear, and you’ve got to listen to those above all else.”
By early 2021, Hightouch was unique among customer data platforms. They pioneered "reverse ETL," a category-defining model that directly syncs internal data from company warehouses to operational systems. This innovation enabled more secure, automated, and personalized customer experiences. (Traditional ETL — short for extract, transform, load — combines data from multiple sources into a consolidated data warehouse. Reverse ETL uses a different engine to change the flow of data— from data warehouses to everything else in a company's tech stack.) This approach laid the foundation for what is now known as Composable CDP.
Fortunately, investors trusted the vision, too. Pre-pivot, Hightouch had already raised $2.1 million in seed funding from Afore Capital and Slack Fund. They’ve since raised more than $170 million across multiple rounds between 2021 and 2025, from investors including Amplify, Bain, Y Combinator, ICONIQ, Databricks, and Sapphire Ventures. They have since reached the coveted status of “unicorn,” with a current valuation of $1.2 billion.
The Unconventional Leadership Model: Two CEOs, One Vision
In the spirit of disruption, Hightouch joined a newer wave of companies debunking the “lone genius” founder myth. Gupta shares his CEO title with Manohar, while Curl, who is CTO, completes the co-founder trio.
“It works for us,” says Gupta. “We keep adopting a fluid mentality — let's focus on making sure that we're set up to solve problems the best. Having that fluid structure has just been amazing because it allows us to do a lot more than other companies do.”
A solid leadership foundation has proved vital as the company’s scaled to a 240-plus-person team across two HQs in San Francisco and New York, plus smaller representation internationally. Gupta says growing a strong team allows him and his cofounders the leeway to fire themselves from roles they may have needed to take on in the past out of necessity.
The trio work fairly independently, but come together to make high-stake decisions. When a decision can’t be made unanimously, veto rights are granted to the person closest to the matter. “We basically make the final call in our domain,” he says.
Meet the Co-CEO Who Swapped Jobs Mid-Flight
Most startups struggle with one CEO. Hightouch has thrived with two—plus a CTO who completes their leadership trio. Discover how Tejas Manohar and his co-founders built a $1.2 billion unicorn by literally switching roles, embracing "domain trust," and proving that shared leadership isn't just possible—it's powerful.
Building on Unconvential Thinking: GDPR, Global Markets, and Cultural Bridges
Gupta sought to address privacy regulations, such as the European Union’s General Data Protection Regulation (GDPR), before American competitors even considered them. This paid off as 25% of Hightouch’s business comes from Europe, the Middle East, and Africa.
GDPR aims to give individuals more control over their data — a beast of a challenge for businesses looking to understand and act on customer behaviors. But because Hightouch works directly with a company’s existing data warehouse rather than duplicating data into separate tools, companies can better comply with GDPR requirements.
“I feel like we're finally now able to really prioritize these other regions,” says Gupta. “We really think that because of how common this problem is of wanting to use customer data to personalize marketing, there's no real inhibitors for us to be able to grow in those regions.”
Over the last three months alone, Hightouch’s Europe-based team has tripled as the company doubles down on underserved markets like France, Germany, and the Nordics, as well as unexpected segments such as luxury retail, given the high lifetime value of purchase in this space.
“We'll base our investments not only on past data, but also on qualitative indicators of future opportunity,” says Gupta. “We really do have customers all across the globe right now, and I think that will only continue to increase.”
Gupta’s 80% Rule (and Other Counterintuitive Wisdom)
Gupta strongly believes that if you’re making the right decisions 100% of the time, you’re probably not taking enough risks. His philosophy? CEOs should aim to be right about 80% of the time.
It’s all rooted in an innate curiosity and willingness to take calculated risks.
That mindset is difficult to teach — and even harder to orient a team around. “It’s really difficult to explain to a team that you need to be correct only 80% of the time in order for things to go ultra well,” says Gupta.
That’s why transparency is non-negotiable. “Internally, we’re brutally honest,” Gupta says. “If you hire smart people, they can tell when you’re not sure. They can tell when you’re making things up. The energy they get from that honesty is way better than from false confidence.”
This candor extends beyond internal decision-making. With customers and investors, Gupta prioritizes openness through product performance and real results — not fluffy marketing, trend-chasing, or obsessing over competitors. His core belief: show, don’t tell.
And the results speak for themselves.
- FabFitFun doubled new-member purchases and increased email-driven sales by 8% after using Hightouch to sync rich customer data from their warehouse to Braze for highly personalized campaigns.
- WeightWatchers boosted new-member conversions from Meta by 52%, cut onboarding time from two weeks to five minutes, and reduced data costs by 80% through more precise audience targeting.
- Meanwhile, Grammarly used Hightouch to personalize billions of emails and manage a 9-figure ad budget across 8 ad networks.
When it comes to Hightouch’s customers, “our retention has been above 90% every year,” says Gupta. “I think our principle is to really care about how the customers are onboarded, how much value they’re getting out of the product, and help them adopt future use cases. The best defense is offense.”
Building for the Future
Startups can be all-consuming and the personal cost of building Hightouch isn’t lost on Gupta. But he believes that the high level of investment now will pay off in the long term.
“The way I think about it is, if we can make meaningful wealth happen for our employees and ourselves, then that gives us more time to spend with our families later in life,” says Gupta.
Last year alone, 19 employees took parental leave, a significant measure of success for Gupta when it comes to company culture. Hightouch’s parental leave policy offers between three and four months of leave, well above the average paid parental leave in the U.S. private sector, which is typically between four and eight weeks.
“Many shared with us, ‘Because the company is doing well and I feel secure in my career, I’m excited to have kids,’” says Gupta. “I'm pretty pumped to be able to do that for myself as well.”
The Modern Immigration Debate Through an Entrepreneur's Eyes
“Every privilege or piece of luck I have today is because of my parents,” says Gupta. “None of this would have happened if they hadn’t taken a big bet on moving to the United States and investing in me.”
The current immigration landscape, however, presents a daunting reality that could prevent others from making the same leap. It’s a prospect Gupta finds disheartening.
While he refrains from weighing in on specific policies, Gupta offers a thoughtful perspective: he worries that fear and uncertainty around immigration might make talented individuals hesitant to come to the US. “Discouraging folks from immigrating is hugely risky to every economy we have, including technology and beyond,” he says. He hopes immigration decisions will be made with greater thoughtfulness and nuance, rather than broad public debate.
In Gupta’s view, America’s competitive advantage depends on welcoming ambitious people who choose to build their futures on US soil. His own story illustrates the multiplier effect of one immigrant founder creating hundreds of American jobs.
Looking Forward
As Hightouch moves ahead, Gupta envisions it leading “true customer intelligence,” empowering companies to act not just faster but smarter. “What I mean by this is we will be able to tell our marketers and our users what they should do to improve the customer experience for their customers or the LTV for their customers more proactively.”
A newer offering from Hightouch is AI Decisioning — an agentic AI product which Gupta says “can help customers more autonomously run the best marketing for every individual customer, as if you had one marketer per customer in your database.” When prompted with a particular goal, the product can run thousands of experiments to inform optimal campaigns.
Agentic AI is only growing, and Hightouch wants to be at the forefront. As the company breaks down in its own blog: while AI agents are software programs that handle very specific tasks, agentic AI can make autonomous decisions based on customer interactions and actually act on them with minimal human direction. Hightouch’s client Whoop — a health and fitness company producing wearable devices — for example, is seeing a 10% increase in upsells from this implementation.
Image © Hightouch
“That kind of proactive suggestion is what marketers have wanted for 10 years,” says Gupta. “It was not possible without agentic AI. And it's also not possible without the exposure to data that we have. Very few companies in the world have exposure to a brand's full customer data set the way we do.”
Redefining the American Dream
From a five-year-old in Haryana to a unicorn CEO in San Francisco, Gupta embodies — and perhaps redefines — the modern American dream.
“I’m very happy with what I have,” he says. “I don’t really need more in my life.” And, as his parents grow older, he’s focused on spending time with them; that and helping to reframe Silicon Valley’s values around immigrant founders and the undeniable opportunity they can create.
“All of these things are highly non-probabilistic for someone of my background,” says Gupta. He wishes that weren’t the case. Until then, his success story is a powerful example of what’s possible.
Author: Brianne Garrett
Brianne Garrett is a journalist, editor, and producer focused on entrepreneurship, lifestyle, and food. Before pivoting to freelancing, she held editorial roles at brands including Sweet July, Forbes, and Wine Spectator. She’s also the founder of Stella, a newsletter, podcast, and community platform that champions and connects Black women in media. A dual citizen of the United States and the United Kingdom, she splits her time between London and New York. She’s both a tiramisu lover and a Chardonnay hater.
