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Drew Williams
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Nick Dauk
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Kristen Anzelc
In fact, the founder and CEO of TribalScale has watched industries bottom-out and businesses crumble – including his own.
Jaitly has seen, felt, and contributed to failure – and it’s created a foundation for success that’s made him Swagger’s latest Self-Made Man.
Sheetal Jaitly only knew Hindi by the time he started kindergarten. The Toronto native was born of immigrant parents, and though he lacked knowledge of the English language early on, he certainly learned to communicate in the language of business far younger than most entrepreneurs.
“My dad did very well in real estate and I learned how to speak in a business development sense from watching him work,”Jaitly said.
He recalled being eight or nine years old when he got his first taste of sales. Jaitly’s father was selling multiple houses on the same block, asking Sheetal to wait for a potential buyer in one house while he checked on another next door. Not content to twiddle his thumbs, Sheetal mimicked his father by showing a couple the house, room by room, and sat them down to fill out letters of interest.
“This lady started crying in front of me,” he remembered. “She’s like, ‘I can’t believe we’re making our biggest financial decision ever and a kid sold us the house.’”
The couple did purchase the home, and while this taste of success created a powerful memory, Jaitly’s entrepreneurial spirit was more impacted by the taste of failure that came a few years later when the housing market crashed.
“My family almost lost everything,” he said. “I held my baby sister in my arms, and even though I was twelve, that was the day that I became an adult. I had to figure out what to do to make sure that this never happens to my family again.”
The deep-voiced teenager worked as a telemarketer, worked in factories, in retail, and even bought an old computer so he could create resumes for people. After graduating high school, his father encouraged him to develop a career so he started in the shipping and receiving department of Keating Technologies.
“I got exposed to the developing tech scene and learned more at work than I did in the college courses I was taking,” he said. “I saw what rapid growth from 30 to 300 people looked like.”
He also saw what another industry collapse looked like.
When the tech bubble burst, he was eventually laid off. Coupled with losing loved ones at the same time, Jaitly fell into a depression.
“I think a lot of men and women in their early 20s don’t know what to do next with their lives. You think you have the world figured out on your path then you’re left confused. My dad was the one who told me to get up off my ass and push grocery carts if I needed to. He told me to go out and keep learning, so I did.”
Jaitly landed at Ricoh as a copy machine salesman, immersing himself in the product, the fast-pace, and the earning potential. He learned how to sell, how to hustle, and how to learn from those around him. A customer poached him, forcing Jaitly to learn how to sell predictive analytics and data sciences.
It was an emerging technology in the mid 2000s and Jaitly had to figure out how to sell a product that his clients didn’t know existed and convince them to spend money they hadn’t budgeted.
“I had to learn to empathize with our clients. I literally worked with former NASA rocket scientists so it was a matter of using this knowledge to create a holistic plan for my clients that would result in a win-win situation.”
Evidently, his math checked out and he was poached once again. After a small stint as a director-level employee at only 27 years old, he joined his friends at the newly launched Xtreme Labs, and helped grow the business to $37.5m in revenue in five years.
But as Xtreme Labs was acquired by Pivotal, and then by Dell, Jaitly struggled to find his place.
“I had the money to make the home with a white picket fence dream a reality. But I wasn’t happy. I was just one person at a desk in this big machine where I didn’t feel like I made an impact.”
Jaitly started TribalScale in November of 2015, walking away from a solid career that he knew could provide the financial security he fought for so desperately since watching his parents’ financial foundation crumble. Instead, he saw a gap in the market and was excited about the potential to produce five-star digital products and transform enterprises in Agile ways.
He didn’t need to wait long for TribalScale to land its first big client. Jaitly was half-way through his pitch for one of the world’s largest media companies when the decision-maker – a former client of his from Pivotal – told him to stop the presentation.
They told him bluntly: “We’ve been working together for five years. You once could have sold me a big product that I would have bought with no hesitation, but you didn’t. You said I wasn’t ready for it and coached me on why it wasn’t right for my business. I realized that you rejected the opportunity for a huge commission just to do what was right by me.”
The client handed Jaitly a $1.2m contract and TribalScale was suddenly in big business.
“A lot of people in business – and in life in general – look to take, take, take as opposed to looking at life through an empathetic lens and doing what’s right for nothing in return. What they don’t realize is that doing what’s right comes back to you exponentially when you develop the right bonds.”
In three years, TribalScale earned just over $50m in revenue, grew the staff to 250+, and had seven offices around the world. Then, they imploded.
“Boy doesn’t life hit you in the face when you think you’re doing everything right.”
Jaitly said that TribalScale grew too big, too fast. Their culture was ruined. Their fundamental practices weren’t followed. They were doing business in areas where they had no business being in.
“It’s easier to walk away and start over, but I looked at this mountain of a task in front of me and decided to start moving it rock by rock.”
Restructuring a business is never easy, especially when there’s a pandemic on the horizon. The first months of 2020 saw TribalScale lose 80 percent of their customers. Instead of severing ties, Jaitly did the unthinkable: he reinvested in his clients at no charge.
“Shit hit the fan for the whole world but we stood by and did what was right for our clients.”
We all know the end of this story: budgets came back quickly as digital products and services became more important than ever. TribalScale met these challenges with a Tribal mentality: taking care of the weak in your group brings strength to everyone.
Sheetal Jaitly has removed ‘transparency’ as one of the three core values that act as TribalScale’s north star.
“We’re still transparent – we can’t solve problems or do our jobs without transparency – but we made the choice to remove it from our core values. The term was used to attack people.”
He used an example that anytime someone would start a sentence with “In the interest of transparency…”, it would almost always be followed by a negative remark that was more politically motivated than professional.
“Taking out transparency as an official core value took away a free pass to be a prick.”
Transparency was replaced with resiliency, a term which complements the other values (empowerment, and challenge and collaborate) quite well. Jaitly believes that his team should feel empowered to create the company that they desire, even if that means creating a safe space where healthy friction through debate can pave the way for new perspectives to thrive.
“A company should be a platform for people to succeed in their careers and in their personal lives,” he said.
“People aren’t clocking into TribalScale just for a paycheck; they want to use their minds in a way that benefits them and the big picture. We look at our staff through a humanitarian lens and wonder how we can help each other excel.”
That being said, Jaitly is quick to point out just how important it is to remove the bad apples – or, in his case, strawberries.
“One of my peers told me about the rotten strawberry theory: if you don’t remove the rotten strawberry from the pack then it spoils the others. I never got rid of employees, especially those who were great performers with bad attitudes. I wanted to work through it, but now I see that to be mission-oriented for the company’s sake, I have to be friendly – not friends – with my employees.”
Jaitly understands that the high-pressure start-up environment isn’t right for everyone, and that’s more than acceptable. He’d rather help them get a job that they’ll love elsewhere.
“You’re not a bad person if you don’t agree with our vision or want a steady nine-to-five job. Let me coach you to get a job you’ll be excited about. Let me hook you up with a different job so then we all win, are successful, and are happy.”
Today, TribalScale is building five-star digital products, transforming organizations with their TribalDNA, and running a start-up studio to create solutions to tomorrow’s problems. Jaitly is currently enrolled in the OPM Program at Harvard Business School where he’s learning how to be a better CEO.
“I don’t want to let down the people that are with me,” he said. “I want to make sure their families and careers are on the right track and challenge them to do better for themselves.”
When looking at a future that may include other forms of failure, Jaitly admits that his failures at TribalScale have encouraged him to diversify his risks and constantly look for leaks in the boat. More importantly, he acknowledges that success and survival depend on one important factor that’s not born of the business.
“You don’t get anywhere without having people in your personal life be your rocks. We too often talk about individuals in the organization and the impacts they make, but I’m also cognizant that I have a supportive family that challenges me. Those who work with me also have personal units that are supporting them. There is no ‘me’ without most people in your life. We are successful because of the ones making sacrifices to support us at home.”
I don’t need a payoff for my actions. We’re in the people business; we all have different motivations. If you’re working with me and it’s not the right place, I’ll still do what’s right by you. I’m not looking for a transactional relationship; I’m looking to do what’s right for all of us. When employees self-select out, I get to help them flourish elsewhere instead of outright letting them go. If you can’t have transparent conversations with your employees or clients then your company won’t get the ancillary benefits that create a healthy company culture.
It’s not advice, but I blame myself for my past temperament and not being patient enough. It’s been a long process over these last five years, spending time trying to not overreact to situations. I grew up a fighter so my first instinct was to react. Now, I try to approach a problem or conflict with a clear mind, determine how to get to the root of the problem, and figure out a solution. In business, we’re taught to act rigid and formal as leaders but it’s more beneficial to interact with employees on a human level.
Having someone you trust — someone who you can go to openly with humility – is key. You need someone to talk to about your weaknesses; preferably someone outside of your business who really understands your business. You need to have confidential conversations with those who will tell you when your shit may stink.
I may know where some of my failure points are but I love it when the people I trust point out my blindspots.
I started this company in my 30s and would always put big goals on the board. When naysayers didn’t think it could happen or when I saw someone not making it happen, I’d do it myself just to prove that I could get it done. In my 40s, I won’t do that. It’s rewarding bad behavior. In my role, I should be the one to jump into the task with an employee who’s struggling, but they’re going to do the work. My ego once drove me to do all of the work myself just to say ‘I told you so’. Now, I want to be a better coach and delegator.
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