Kit Chandra's Philosophy for Closing Multi-Million Dollar Deals

When Kit Chandra hits quota, he buys a luxury watch.

Kit has a lot of nice watches.

His favorite, a brightly burnished Jaeger-leCoultre, glitters in the dim light of a dinner party in the Oakland hills. I’ve just settled into the chair next to Kit. A partygoer passes by, and breezily says something that stops me cold. 

“Kit’s like, the Michael Jordan of sales.” 

Kit doesn’t know I’m scouring the globe for the world’s best salesperson, so it feels like the universe is doing me a solid by crossing our paths on this rainy California night. The next day, I tracked down his number and set up time to dive into Kit’s story. 

By the end of our 90-plus-minute conversation, I’m mostly on board with that description.

You see, Kit manages some of Twilio’s (NYSE: TWLO) largest accounts — household name companies anyone would recognize. He’s a multi-time President’s Club member. The biggest deal he’s closed (outside of renewals) is well into the millions.

Kit is extremely legit.

Now, I’m not about to name anyone the GOAT. But no one said he is the Michael Jordan of sales. They said he’s like the Michael Jordan of sales.

And like MJ, Kit didn’t start at the top. He had to fight and scrap to get there — self-imposed retirement and sport change included. 

Gatekeepers Love an Edible Arrangement

After college, Kit wanted to pursue a career as an actor (something he’s still mulling over). Kit’s father was supportive, to a point. 

“Trying to tell your successful father you want to be an actor was like walking face first into a wall full of knives,” Kit says. His father told him he could be an actor — if Kit agreed to repay him for all of college.

Kit didn’t love that idea, so he looked for a job that could make him lots of money. Naturally, that led him to his first sales gig.

“My first job was commission only, which looking back, it sucked, but it was a great way to get into sales because you ate what you killed,” Kit says.

From there, he landed a role at Athenahealth as an enterprise business development rep. Tasked with getting past Executive Assistants to set meetings with their high-flying bosses, Kit displayed the first of many skills that make him one of the world’s best salespeople: Kit often says the thing you shouldn’t say. 

“In one of the big deals I set up at Athena, it took four months of calling. I made friends with all of the EAs. I said, look, I need 15 minutes with your boss. I also know your job is keeping me from getting 15 minutes with your boss. What can I do to help you understand why we want to talk?” 

Enter the second of Kit’s sales superpowers: his ability to build authentic relationships with just about anyone. When the holidays rolled around, he sent each of these EAs an edible arrangement. Not from some stranger, but from a friendly voice they’d come to recognize.

That worked.

“Sure enough, I got a meeting with an SVP or higher in every single case.” 

Following a successful tenure as a BDR, Kit was promoted to an account executive role. And that’s when things started to fall apart. 

Getting Fired at 24 Was Exactly What Kit Needed

After a year of struggling in a closing role, Kit got hit with a PIP — and shortly thereafter, was let go. 

“I remember when the HR person was walking me out, she was trying to be super nice. She asked me, ‘So what are you doing this weekend?’ And I was like, ‘I don’t know, getting fired?” 

When I ask him why, after so much success in a BDR role, he failed as an AE, he puts it like this. 

“As a BDR, your job is to fill the very top of the funnel. With the loosest of qualifications. When you go into being an AE, all of a sudden you need to learn how to navigate an organization. You’re the CEO of your team, the buck stops with you.” 

Kit took some time off. He backpacked around Asia and then moved to California.

“It was scarring to my ego, and humbling. But getting fired was the best thing that happened to me at 24, because it taught me that getting fired wasn’t personal. Either I am not right for the job, or it’s not right for me — it’s just business.”

In his new home base on the West Coast, Kit landed a customer success role — his proverbial retirement to pursue baseball. He thrived in a post-sales environment, landing promotion after promotion. But every year or two, his bosses would pull him aside and urged him to get back into sales.

Saying the Thing No One Wants to Say

By this point, Kit was a Director of Customer Success — and he was feeling burned out. So he took a sabbatical, another four months off to clear his head and think about the future.

Something kept calling him back to sales. His roommate, a longtime Twilio employee, got him connected to someone looking for a Kit — they were putting together a team of strategic account managers. Right up his alley. 

Kit landed a role as a Customer Account Executive, managing a book of over 50 accounts ranging in size from less than $100k ARR to millions.

Looking to de-scar the past, he dove in headfirst, determined to succeed. 

“I just ate, slept, and breathed Twilio,” Kit says. “I threw myself into every part. Not only selling but understanding the product. I didn’t wait on sales engineers. I’d read the technical documentation, read the MSA, and go in alone.”

With his product knowledge dialed in, Kit’s priority was to deliver extreme value and cut to the heart of his customer’s problems.

“We were tasked with increasing the contract value on our accounts. So I just called their CFOs and said, look we have you predicted to spend X. If we change the structure of your plan with us, I think I can save you some money. I’d ask them how important it was for them to achieve economies of scale — CFOs love that phrase, by the way. And they were like, of course, let’s get this done.” 

The way Kit says this sounds totally normal and reasonable — but it runs counter to everything most buyers expect from salespeople. How often does your account exec start by trying to save you money? 

“The first thing I’d try to understand is if we’re revenue generating or not. I’d read up on their competitors, and ask them about what was going on there,” Kit says. “I don’t know if that’s a challenger sale, but I’d really try to unlock their business.” 

Kit’s no-nonsense, value-first approach opened the door to introducing net-new products and orchestrating account expansions. In his first full year, he made President's Club. 

Peacocks Don’t Make Friends

But it wasn’t all sunshine and butterflies. At the President’s Club trip that year, a colleague pulled Kit aside. In front of Kit’s manager, they delivered some harsh feedback.

“Man, you’re really good at sales,” Kit’s colleague began, “but none of us like you. You’re a peacock. You brag too much.” 

Kit remembers his manager reaching over and patting him on the shoulder — silently affirming this feedback. 

Once again, Kit was humbled. Yes, Kit was the CEO of his accounts — but his success depended on a whole team of people who worked together to make those accounts successful. Kit thought he’d been amping people up by telling his colleagues about his wins, not realizing that could easily be interpreted as bragging. So, he toned it down and took the lesson to heart. 

The next year, management gave him a reward for his hard work: a bunch of accounts nobody wanted.

“I started digging into these accounts, and I realized why no one had been able to turn them around. No one was speaking their language,” Kit explains. So he dove in, taking ownership of the accounts from top to bottom. He set up as many in-person meetings as possible and said the things nobody wanted to say. 

“Sometimes, it’d come down to saying, ‘We have no idea how your business has changed in the last three years, and I don’t think that’s a good thing. I’m not just here to collect money from you,” Kit explains. “That’s a very endearing, curious thing to say as long as you say it right.” 

With a mix of charm, honesty, and humor, Kit got even his most adversarial buyers to open up — which allowed him to be the bridge between Twilio and his customers' organizations, aligning needs, clearing contract terms with the deal desk, and removing roadblocks to get deals done.

Kit’s Philosophy for Closing Mega Deals

Almost five years into his tenure at Twilio, Kit made President’s Club three times in the last four years and was the top AE in the North America region in both mid-market and enterprise segments. He’s carried quotas in the tens of millions, added millions more in new revenue, and just generally crushed it. 

I told you. The MJ comparison isn’t far off.

When I ask Kit how he deals with the pressure of carrying a multi-million dollar quota, he hits me with some unexpected philosophy. 

“Not to get too San Francisco on you,” he starts, raising some mild alarm bells in my head, “but there’s an old Buddhist proverb that says if you want to win an archery contest, don’t aim your bow at the trophy.” 

I’ve never heard that before, but I like it. It rings true to me; I’ve carried my fair share of quotas. Stay in the game long enough, and you’re going to miss eventually. What’s more important is what you do next.

“The more you try to make a sale, the less you’ll make a sale,” Kit says. “The more you try to understand, the more you try to connect, the more you try to build actual influence based on logic and emotions, the better you end up doing.” 

I catch a glimpse of Kit’s watch at this point, and am surprised to see that we’ve been going for over an hour. I plumb him for one more tidbit of wisdom, something one of the world’s best enterprise reps can share with the broader sales community. 

“If you’re a salesperson, your job isn’t to sell anything. It’s to bridge the future success of your company to the future success of your customers,” Kit says.

It is, in other words, all about knowing where to aim your bow.

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