I followed the CEO of $5.7 billion Okta around and learned the secrets of a tech conference that landed President Obama as a speaker

Business Insider/Julie Bort

Last week, the conference center at the Aria hotel in Las Vegas was abuzz with excitement. Okta, the $US5.7 billion identity management company, had landed a very special guest speaker in the form of President Barack Obama.

Okta has a classic Silicon Valley origin story. It was founded by two early employees of Salesforce: Former Salesforce engineering head and current Okta CEO Todd McKinnon, and Freddie Kerrest, who had been a sales exec at Salesforce, and is now COO of Okta.

When they first decided to pursue this company, no one believed in the idea. Salesforce and its gregarious CEO Marc Benioff are known for investing in the startups of ex-employees – but they never invested in Okta.

With little support, the two of them started with nothing and had to do all the initial programming themselves. But after they signed on their first customers, hundreds, and then thousands of cloud app companies began coming to them. Andreessen Horowitz invested and Okta soon became a Silicon Valley VC darling, hitting a “unicorn” valuation of over $US1 billion in 2015.

In late 2017, the company had a successful IPO. Sales have been beating expectations and the stock price has doubled since then. Okta now has over 4,300 customers, 33,000 developers are building apps on its platform, and it hit $US260 million in revenue last year. They welcomed 4,000 people to this conference in Vegas.

Okta was so excited to be hosting President Obama, the company invited Business Insider to tag along for a behind-the-scenes look at what it takes to put on their tech conference, and what they had to do to host the 44th President of the United States, who still enjoys enormous popularity in the tech community.


The day before the conference opened, I met up with Okta cofounder and CEO Todd McKinnon at the private executive room his team had reserved for the week. He was drinking an espresso to get charged for the afternoon. (He is a coffee fanatic.)

Business Insider/Julie Bort

Cybersecurity folks can often be reserved bordering on secretive. But not McKinnon. He’s friendly, open, and cheerful with a dry wit.

And he has a strong vision for how passwords are evolving into digital identities, and what his company needs to do protect people as more and more of their lives are managed online.

His keynote this year was aimed at sharing his vision with his customers, the folks responsible for protecting people’s online identities.


Later, we’ll catch McKinnon blowing off steam by walking across the stage on his hands.

Business Insider/Julie Bort

He doesn’t do this trick during his actual keynote, but he’s famous for taking a break during long meetings at the office in exactly this way.

He can walk a good six feet on his hands, thanks to his love of CrossFit. When he’s not running Okta or hanging with his family, he’s competing at the national level, doing events involving days of cardio, weights and shows of strength like this handstand walk.


The private executive room where we first meet up is lux.

Business Insider/Julie Bort

It includes a kitchen stuffed with snacks and an espresso machine. It will also serve various meals during the day. It has two private studies and a conference room in back.

That’s Okta’s head of PR Jenna Kozel in the foreground. She’s one of my guides for the day.


Here’s a somewhat better picture of Kozel (left) and a terrible picture of me.

Business Insider/Julie Bort

And I’m clearly not aiming the camera well for this selfie.


Everyone is psyched about this year’s conference because President Obama will be here. He doesn’t accept very many corporate speaking gigs, so the Okta crew was jazzed — and surprised — when he agreed.

Business Insider/Julie Bort

It turns out the Obama Foundation is an Okta customer, using it to manage their passwords. So Obama’s peeps knew the company.

Okta still had to jump through a lot of hoops to get him to appear, which included having Obama’s team vet the company for any scandals, a long negotiation on the types of questions that would and would not be asked, and months of paperwork.


Obama still can’t talk about a lot of top secret things in public, and he won’t talk about the current president. “There’s a rule of honour that past presidents don’t undermine current presidents,” one person told us.

Okta. Used by permissionBarack Obama enters to a standing room ovation crowd at Okta’s Octane 18 tech conference in Las Vegas, May 24, 2018

On top of the rules, there was a sizeable speaker’s fee to pay. Okta wouldn’t comment on much that fee was, but Obama has been known to command fees of $US400,000.

It’s not clear that Okta paid that much. A speaker fee in the $US200,000 range would be more typical for a headliner of Obama’s stature at a 4,000-person conference.


Another one of our guides for these days is McKinnon’s executive assistant Tanya Benvenuto. She’s the smiling, behind-the-scenes general taking care of a thousand details. For instance, she’s the keeper of McKinnon’s conference badge.

Business Insider/Julie BortTanya Benvenuto

She keeps his badge because at Okta’s his first-ever conference a few years ago, he didn’t have one, and the security guards wouldn’t let him in to deliver his keynote at his own conference. Because he’s the CEO, no one thought to register him for the event, so he wasn’t wearing a badge. This year, Benvenuto makes sure that his badge is always close by, so he can have it if he needs it.


This show is the baby of Okta’s CMO Ryan Carlson. He’s the MC of all the on-stage activity and his team has been working for more than a year to pull this show off.

Business Insider/Julie Bort

He’s one of the reasons President Obama is speaking. When his team was brainstorming names for the keynote speaker he kept telling them that the theme of the show was “Beyond” and they needed to think bigger.

“Who is the person everyone most wants to hear?” He asked.

“Obama,” one person replied.

“Well, then, let’s try to get him.” And it worked.

Moral of the story: always try for what you want, first, even if it seems impossible.


The day before the show opens the top brass do a full dress rehearsal for the keynote, which includes all the slides, videos and guest speakers.

Business Insider/Julie Bort

Some of the guest speakers like to run through their interview. Others prefer to wing it on stage. But they still work through executive entrances, exits, demo setups, PowerPoint slide checks, and so on.


The dress rehearsal takes more than 2 hours, longer than the actual keynote.

Business Insider/Julie Bort

There’s a lot of stopping, making a last-minute change, and then restarting. McKinnon has already put in over 18 hours of practicing his keynote speech before arriving in Las Vegas and he’s got it pretty well memorized, although there’s still a big teleprompter guiding him through it.

It’s gruelling and by the end of it, everyone is punchy, hungry and cracking bad jokes on stage instead of repeating their speeches.


Here’s one secret trick of the trade. Benvenuto has brought the suit McKinnon will wear on stage to the dress rehearsal. After the rehearsal, he puts the suit on and poses for pictures. These will be released to the press when the keynote begins and they look like they were taken live — but they weren’t.

Business Insider/Julie Bort

McKinnon is under strict orders not to break into a handstand while wearing his keynote suit for fear of ripping his shirt.


The morning of the keynote starts early. We all meet backstage where the executives get kitted out in stage makeup and professional hair styling.

Business Insider/Julie Bort

After the keynote McKinnon will make a beeline for the bathroom to wash off his makeup. He doesn’t leave it on for his day of customer meetings. But he’ll have to get another dose of it before the big evening event on stage with Obama.


The stage does have an official green room, but the speakers don’t use it. Everyone just gathers informally at a table backstage.

Business Insider/Julie Bort

There’s a breakfast spread serving food, coffee and drinks.

That’s Tereasa Kastel, a VP at American Express, which is an a Okta customer. She will participate in the keynote, and also talked to Okta’s other cofounder and COO, Freddie Kerrest, on stage.

Benvenuto is grabbing a bite and chatting with another Okta staffer, too.


There’s a few other VIPs wandering around backstage, like this customer who chats with McKinnon before the keynote.

Business Insider/Julie Bort

During the keynote, McKinnon unveiled a bold vision for his company. That’s good, because Okta has some huge competitors these days, including Microsoft, Google, and RSA, a subsidiary of Dell.

Okta. Used by permission.Okta CEO Todd McKinnon

McKinnon is fending off his giant competitors in several ways. Because Okta basically created this market, it has a head start and a lot of customers.

It is using its large network to see across the whole internet and build new products for customers based on those insights.

For instance, Okta unveiled a new tool called Onramp, that is something like an app store. It will help its enterprises find new cloud apps used by other companies similar to themselves.

This announcement led to one of the funniest moments of the day…


The funniest moment came from a video from Box CEO Aaron Levie, a longtime buddy of McKinnon’s.

Business Insider/Julie Bort

Levie and McKinnon launched their companies around the same time and have been partners for ages.

Levie had been pushing McKinnon to do an app store like Onramp for ages, so he volunteered to help introduce it – but he was unable to attend the conference in person. So he chose to film a funny video where he tried to introduce President Obama, only to be told he wasn’t on for that.

Levie is definitely the closest thing that enterprise software has to a stand-up comedian.


Okta is also establishing new partnerships with big companies like Facebook.

Business Insider/Julie Bort

Facebook is one of Okta’s initial partners for Onramp. That’s why Facebook’s Lesley Young, head of global enterprise sales for the Workplace by Facebook product, came onstage to talk about the partnership.

This was interesting because McKinnon also announced a tool that lets people sign up to websites. It competes with one of Facebook’s most popular initiatives, “Facebook Login,” which is the popular tool for using your Facebook ID to sign in to apps. Google offers something similar, as well.

McKinnon said that the world needs “an alternative” to logins from ad-supported companies.


McKinnon then shared his bigger vision with the crowd.

Business Insider/Julie Bort

He wants his customers to help him build a way to create safe, protected, digital identities for people, just like the internet does for servers.


How can you verify who you are online for all sites from social media, your bank, the hospital and all the apps you use? In one place? With the data controlled by you, not all of these individual providers?

Business Insider/Julie Bort

He wants to create a system for digital identifies for people that travels with them across the net, the same way a driver’s licence or passport might travel in your pocket.

He wants a system that does for people what the Domain Name System (DNS) does for servers. With DNS, no matter what browser you use, you can type in a URL and get to the website.

This is a big idea that will take years to do and will require the buy-in from his customers, and from the world’s identity security experts, he tells the crowd.


After his keynote, we all head backstage. McKinnon’s parents were there, partly to see their son, the CEO, and partly to see Obama’s talk later that evening.

Business Insider/Julie Bort

With the keynote over, McKinnon is already rubbing off the stage makeup.


Mckinnon then greets and chats with the incomparable Aimee Mullins. Mullins is an athlete/track star, model and actress on Netflix’s “Stranger Things” famous for designing her own prosthetic lower legs.

Business Insider/Julie Bort

Mullins is just about to go on stage and give one her world-famous inspirational talks.

She’s a double amputee who helped usher in a new era of beautiful prosthetic legs specially designed for all sorts of uses, from athletics to high fashion. She’s one of the most popular TED Talk star lecturers, ever.

Her talks help people question the kinds of limitations we put on ourselves.


But after her talk, when the whole keynote is over, McKinnon is ready to show off his handstand walking skills again.

Business Insider/Julie Bort

Mullins sees him do it, and because she’s an former Para Olympic athlete, she wants in.


So we head out onto the stage where there’s more room and Mullins teaches McKinnon how to do a split-leg headstand.

Business Insider/Julie Bort

“This takes a lot of core strength,” she says as she easily raises up.


Mullins’ split leg headstand looks a little better than McKinnon’s.

Business Insider/Julie Bort

I would like to try it, too, but I’m wearing a dress and there’s a small crowd gathered around. So I remain with my feet firmly planted on the floor.


As the afternoon wears on, closer to Obama’s evening talk, we see the first evidence that Obama has arrived. Security becomes tight! His team has cordoned off an entire lower section of the conference center behind those black curtains.

Business Insider/Julie Bort

Not only are we not allowed past the curtains, but the security guards aren’t allowing anyone to loiter too close to them, either.


Here’s what’s going on behind the curtains …

Business Insider/Julie Bort

But Obama has agreed to take personal 1:1 photos with VIPs as part of his appearance at the conference. The list of those people who get photographed with him has been submitted in advance.

Those with backstage passes (special wristbands) are allowed behind the curtain. And we gather together and chat. People are excited about meeting the president. The list includes VIP guests of Okta, as well as people who don’t know the company but are friends of Obama’s staff.


We are given slips with our names and our number and asked to line up in order, a bit like a ticket on a Southwest flight. We cannot bring bags or phones into the room with us where we meet Obama (so I couldn’t take pictures of it).

Business Insider/Julie Bort

People enter the room and stand in a line cordoned off by a velvet rope.

Another black curtain blocks the line from the president. This is not only a security measure – it also controls the lighting for the photographer.

Okta cofounders McKinnon and Kerrest, plus their wives, came in for five minutes of private prime time with Obama before the photo opportunity officially began.

For the picture, a member of Obama’s staff tells him your name and he chats for a few seconds, and cheerfully poses for the picture. There were a good 100 people lined up. He’s a trooper to agree to take photos in a marathon session like this.

The photos are for personal use, not licensed for commercial use, so I’m not allowed to publish mine on Busienss Insider. Here’s my tweet, thought.


Closer to the talk, people have filed in and are waiting well in advance.

Business Insider/Julie Bort

There’s a cheerful nervousness to the crowd.


I’m hanging backstage with McKinnon and we chat about his questions. He’s not nervous but he feels the expectation. “I want to do a good job,” he says.

Business Insider/Julie Bort

No one else is back there with us, as we sit at a table and talk about what kinds of questions he should ask Obama. All of Okta’s staff has grabbed good seats in front.

It’s so quiet and we’re so focused on what to ask Obama, that I forget to take a picture of McKinnon alone backstage. This is a picture of him earlier, silently watching Mullins’ presentation.


When Obama walks onto the stage, the crowd gives him a standing ovation.

Business Insider/Julie Bort

There’s always a lot of angst over what goes on in Washington, but these days people are feeling especially emotional over the current administration.

Obama is still a very popular and highly-respected president among many people in the tech industry, and he gets a standing ovation as he walks on stage.


McKinnon gets over his nerves and Obama is relaxed and happy on stage. He discusses tech, taxes, privacy, his Netflix deal, basketball, life in the White House, life after the White House and cracks the crowd up with his jokes.

Okta. Used by permissionBarack Obama and Okta founder CEO Todd McKinnon

Read more about what he said on stage here:

Obama explains why he signed a deal with Netflix and how he thinks it will help solve our political divide

Obama and his friends were so competitive during their White House basketball games, he wound up with stitches

Obama describes what being in the Situation Room is like – and it’s advice anyone can use to make hard decisions

Obama made a joke about ‘the modern presidency’ and people ‘going to jail’


After the successful talk with Obama, the next day’s schedule is filled with customer meetings. I was allowed to be a fly-on-the-wall at one of them but the conversation is off-the-record so I can’t repeat tell what I heard. But here’s the evidence of this meeting …

Business Insider/Julie Bort

That’s McKinnon’s shoes on the right and the customer on the left.

They talk about using Okta’s products to do all kinds of cool new things and that’s all I can say.


Next up: a press conference where Okta’s co-founders McKinnon and COO Frederic Kerrest explain the vision for digital identities.

Business Insider/Julie Bort

About a dozen international reporters have gathered to hear more about the vision for digital identities, newly released products that help eliminate passwords, and challenge Facebook’s and Google’s systems for app logins.


The final keynote was a spectacular talk by chemist, doctor and astronaut Dr. Mae Jemison.

Okta. Used by permissionDr. Mae Jemison

Jemison wants humanity to dream bigger. Instead of going to the moon, she wants us to go to a new star system – something “we don’t know how to do.” It’s a project called The 100 Year Starship.

She also wants humanity to have a moment of togetherness in August when we all look up at our shared sky and share our dreams on social media, a project called Look Up.

McKinnon wasn’t able to see the talk. He chose to dash back to Bay Area to attend his daughter’s dance recital.


And the conference closed when CMO Ryan Carlson gave one lucky attendee a brand new Tesla Model 3.

Okta. Used by permission.

Yup. They gave away a car. The lucky winner was Chris Fuller.

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