Meet Orlando Scampington, the newest (and fakest) thought leader in Boston tech

Orlando Scampington, a self-described author, thought leader, dreamer, visionary, and believer in unlimited human potential.
Orlando Scampington, a self-described author, thought leader, dreamer, visionary, and believer in unlimited human potential.

If you were one of the roughly 14,000 people who attended HubSpot’s last customer conference, you might have been lucky enough to catch a presentation from consultant, author, and all-around thought leader Orlando Scampington.

Scampington doesn’t make many public appearances, but it’s not because he’s a busy startup investor or jet-setting executive. Scampington is actually the comedic alter-ego of Tyler Littwin, who works as an art director at HubSpot.

Littwin created the character after finding it harder than expected to write a standup comedy set for an amateur open-mic performance. But soon enough, it morphed into a channel for parodying the cultural quirks of the tech and business worlds, where people are drawn to big ideas delivered with confidence.

Today, Scampington can be found delivering nuggets of business wisdom over at his Twitter account and longer musings on — of course — Medium. “Marketing (along with art, science, religion, & philosophy, etc.) is one of the pillars of society,” one recent post begins. “It is perhaps the most important pillar. It’s at least in the top three.”

Scampington’s speaking style is a play on the legions of self-styled “thought leaders” who tend to populate tech conferences and business meetings of all sizes, fueled in large part by the made-for-YouTube phenomenon of TED talks.

There are a few hallmarks of a Scampington presentation. He discusses extremely broad concepts, but delivers them “as if he’s the one who’s discovered some secret — like, `Leadership is really important,’” Littwin said.

Self-promotion is also essential. “Orlando will have slides where he quotes himself and has his Twitter handle because he wants people to share his ideas. Which is kind of a silly thing to have, but is something I’ve seen,” Littwin said.

And no matter how laughable the idea, Scampington is straight-faced. The silliness is reserved for the slideshow, such as an insanely complicated geometric graphic illustrating the “Zone of Persuasion” approach to winning customers (which relies in part on exploiting a fear of snakes).

Funny business aside, Littwin said there’s real value in staying grounded by poking fun at the seriousness of the white-collar working world. “My wife works in the pediatric ICU. There’s no way I can say that the work I’m doing, or most of the people I know, is more significant than somebody working as a doctor or a social worker,” he said.

Littwin has long been interested in humor and performance. His comedy tastes were formed early by watching TV with his parents, who were big fans of Monty Python. “That was one of the earliest things I remember — you can be very smart and totally absurd at the same time,” Littwin said.

Littwin helped run a satirical newspaper in high school, and a sketch comedy show in college. He also got into music, playing in bands for about a decade — his last band was the rock foursome Thick as Thieves.

He figured he’d wind up in another band eventually, but when that didn’t materialize, comedy emerged as a possible creative outlet. Taking the stage as Scampington, Littwin said, produces the telltale jolt of excitement that can only come from performing in front of a crowd.

“Anytime you’re on stage, you’re going to have some kind of act going on, whether you’re giving a third-quarter sales presentation or doing standup or in a band,” Littwin said. “A lot of the stuff that I try to poke at with Orlando are the people who take it too far. Like, ‘I’m onstage because I’m a visionary, and I want to share it with people because I care about you.’”

The name “Orlando Scampington” was born when Littwin worked at a shipping company — he’d amuse himself by submitting lunch orders under fake monikers that sounded funny when the order was called out.

But Scampington’s persona wasn’t formed until Littwin tried his hand at standup comedy and found it surprisingly hard to write a set. It might be easier, he thought, if I came out in character. “It was a combination of fear and laziness,” he said.

After some fine-tuning with friends and co-workers, Orlando Scampington was ready for a bigger stage. He got it at Inbound, HubSpot’s huge annual customer convention. The topic was “The Pillars of C.L.A.M.,” Scampington’s supposed rubric for business success that focuses on Culture, Leadership, Analysis, and Marketing.

In the YouTube video of his talk, scattered laughter can be heard as Scampington flips through some of his clearly ridiculous slides, including a list of startups he’s supposedly advised.

“The Brimbbler app has disrupted the way deli meats are consumed,” Scampington says. “And, I think it’s safe to say this now, but Google has acquired HorsePunt, which is a big win for me. I’m very proud of that.”

Having one of your employees poke fun at the entire idea of business speakers, the tech industry, and the conferences they populate seems like a slightly risky idea for a company. So why did HubSpot decide to let Littwin try out his satire at its most important event of the year?

“I always think whenever there’s an elephant in the room it’s good to go straight to it,” said HubSpot’s Laura Fitton, who organized the Inbound speaker roster. “Orlando does such a great job of Onion-esque lulling the audience from reality to, `Oh wait, I’m in the middle of absurdity and I didn’t even know you were taking me here.’”

The ruse definitely worked on a few people, Littwin said. Although the Scampington character is not meant to be an aggressive or insulting parody, Littwin was still surprised and a little happy when a handful of people at his Inbound presentation didn’t get the joke and left.

“They had their notebooks open and were taking notes,” he said. “And about five minutes in, they looked at each other and stopped taking notes, and walked out the back thoroughly disappointed.”