Fun, Sun, & Synchronization: At Look Inside EvolutionIQ’s Annual Puerto Rico Offsite

With 2023 off to a roaring start for EvolutionIQ – a valuation now $200 million+, headcount topping 100, contracted revenue having tripled in 2022, and more  – the entire company jetted off to Puerto Rico in early March for a mix of well-deserved beach time and critically important synchronization on the roadmap ahead.

For the machine learning experts at EvolutionIQ, constantly calibrating the models that power our AI is standard operating procedure. Likewise, with so many new clients now using our technology, a rapidly expanding line of product modules, and the number of employees doubling in size last year – continual team calibration is also baked into the company’s DNA.

That’s why before the boogie boards or Havana Banana umbrella drinks were busted out, each core team – such as STD, LTD, Workers’ Compensation, Platform Development, Client Strategy, Information Security, Machine Learning, and more –  hunkered down in strategy sessions to ensure each was aligned with the other. It also gave each team a chance to give all of their peers in other groups line-of-sight into important projects underway.

“When you think about the end of the year and going into 2023, what does success look like?” co-founder Tom Vykruta said in his kickoff talk to the team. “Success for us is if our customers are successful using our software. So everything we do should be thought about in terms of customer success. And it’s not just helping them use our platform. It’s about having technology products that can scale.” 

Tom recounted the story of a top software company that had a great product, and great customer success teams, but their core tech wasn’t designed to scale. Slowly, and then rapidly, most of their time became devoted to fixing new problem after new problem in their core code base. The firm sank because a losing game of ‘whack-a-mole’ replaced customer success as the priority.

“So a customer can start failing because of technology decisions made by a developer who’s not thinking ahead,” he said. “For us, if we are impacting a customer’s claims – reducing losses, increasing returns-to-work, reducing expenses. If our software is working for them. If their staff is excited to use it and can’t wait to get to work in the morning because it’s fast and easy to understand, we will make our customers successful. So every team should think about this, asking, ‘What’s our role in ensuring this customer success?’ All of the team sessions this week here in Puerto Rico should center on the question of what do we need to do – not only today – but through the year and for the future so that we are always planning for a customer’s future success.”

“We’ve reached this incredible point where this year we’re doing probably ten times more technology and product development than we did last year. That’s an unusual pace of scale. So we have to think very hard and carefully so that all of our decisions continue to be designed specifically to ensure customer success.”

Co-founder Michael Saltzman added that another key part of the offsite is synchronization, which is even more important now that EvolutionIQ has grown so rapidly.

“In already meeting with a lot of people since we got here, I haven’t heard a wrong answer on what you see as our company goals,” Mike told the group. “I think we’re all in a great place in terms of where we see ourselves going and what we need to do to get there. So my goal for this week in Puerto Rico is really about connective tissue. We need everyone here, not just the folks who have just joined, but everyone, to be able to navigate not just their job, but navigate our organization to find what they need and make things happen.

“We’re investing a lot in the process and all of the formalities that enable that, but there’s also just that ‘gut instinct’ or ‘gut feeling’ we all need to have. Do you know the person on the other team who is best for a particular solution? Do you have a sense that this person or that person did this before so I know I can go to them? This week is a lot about that. 

“So socialize with people. Get to know how they think about our technology and what they’ve done before. This is a journey but the connective tissue here – the layers beneath the senior team leadership – is what I want each of you to get to know well. We need people to be able to do things – and do them successfully – and that’s not something that you can do alone. You have to know how this organization works.

“So have a beer, go swimming, play volleyball, but also get to know what the people you’re with do, what they’re excited about, what they’ve been successful in. I think we can all do that and have a really good time in the process. It will be a smashing week.”

Here’s a look at some of the groups in action in Puerto Rico.

Fasten Your Seatbelts: It’s hard to cram a week at the beach into 35 seconds, but this video overview captures a lot of work, and a lot of fun, on both Luquillo Beach and in the adjacent El Yunque rainforest.

‘That thing got a Hemi in it?’ Here the teams breakdown the latest new developments in our Disability product lines.


This Year’s Model: Alexey Butyrev explains how the Machine Learning team works to develop and refine the models that drive claims guidance.


People Power: Jesse Samuelson discusses EvolutionIQ’s rigorous recruiting process, which has drawn top talent from Google, Meta, Bloomberg, Palantir and more – and tripled the size of the engineering team over the last year. 


Open Door: EvolutionIQ’s three founders, Mike Saltzman (left), Jonathan Lewin (center), and Tomas Vykruta host an “Ask Me Anything” question and answer period.


The Love Connection: Next time, we should make a giant cardboard “A” and put it in front of the sculpture at the San Juan airport so it reads, “AI hearts Puerto Rico!” – because the ever-growing team has convened on the island three years in a row.


Off Road Warriors: The dirt was flying during ATV rides through the mountains of the El Yunque rainforest.


Nail Yes! Erin Driggers, our manager of platform applications, shows just how proud EvolutionIQ team members can be with her great idea to put our logo to fashionable use. (She nailed it!) And the yawn from Wrenny, the company’s official mascot and Head of Office Pawlitics, summed up the feeling of everyone when finally boarding the planes home after maxing out on so much fun.


Nos vemos el próximo año, Puerto Rico! (See you next year, Puerto Rico!)

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