Feature

Ruby Kolesky Feature

October 25, 2025

Ruby Kolesky is the CEO of Joyous, a cloud-based AI platform that helps organizations get actionable feedback on specific operational topics through private, one-on-one chats at scale. The platform then automatically delivers a detailed action plan for leaders to execute, with no manual work required.

This combination of speed, scale, and AI automation makes Joyous a more efficient, engaging, and action-oriented alternative to legacy survey tools like Qualtrics, and far more dynamic than traditional focus groups or interviews. From day one, Joyous has focused on large, complex frontline workforces, and has recently launched a new self-service option that anyone can trial and purchase directly from their website.

Ruby can speak about a range of topics, including how AI adoption at scale can succeed when done in a structured and transparent way. Joyous is a prime example, having applied AI across 11 of 15 steps in its core workflow and earning the trust of major enterprise customers. In fact, one of the world’s largest telcos selected Joyous as the only vendor allowed to use its own AI infrastructure – something even major players like Salesforce couldn’t achieve.

She also shares insights on how leaders can avoid common AI traps, both when building AI products and when introducing them into large organizations. Ruby believes that AI bottlenecks in enterprise onboarding are now a CEO-level concern, as many organizations risk missing the opportunity to differentiate. While executive appetite for AI is growing, procurement processes are often slowing adoption down.

And despite leading an AI company, Ruby predicts that human interaction will become a premium experience as more organizations attempt to replace customer interactions that should remain human with AI agents.

Ruby first set out to be a stand-up comedian, but when that didn’t work out, she became a software engineer instead. That mix of humor, curiosity, and a deep understanding of people, combined with strong technical skill, has shaped her approach to building human-centered technology. She’s known as a forward-thinking product and data science leader, and a new kind of technology executive who blends strategy, empathy, and innovation to drive meaningful change. You can read her blog to learn more about her and the topics she writes about.

[Q U I C K N O T E S]

Position: Chief Executive Officer
Industry: Tech, AI, Survey
Location: Auckland, New Zealand
LinkedIn: Ruby Kolesky
Website: Joyous.ai
Speaking: Ruby Kolesky

Ruby, can you start off by telling us about yourself and why you chose technology, then leadership as a career?

Ruby Kolesky smiling with her arms crossed.

I originally studied musical theatre and intended to become a comedian. I realized I wasn’t that funny and so did the next logical thing – pivoted to technology (lol). By the time I was 19 I had launched a successful website called Partywatch. We took photos of friends hanging out together at local pubs and clubs which I posted on the site for them to download the next day – this is before Facebook existed and mobile phones had cameras. It became popular very quickly. I got hooked on the thrill of making something from nothing and the endless possibilities of technology. The rest is history.

Can you tell us what drives you to be successful as a technology executive?

My goal is to make a positive impact on as many people’s lives as possible. Many people measure how successful they are based on money or fame – for me it’s the number of people I’ve helped. Even if it’s just in a small way. Technology is a way for me to do that at scale.

Tell us about your vision of your career in the next 2-3 years.

I have a vision for my life more so than for my career. In the humblest way possible, I feel I’ve already made it.

As for my life vision: I care most about being part of something bigger. I am obsessed with succeeding despite the odds – achieving the ‘mission impossible’ – being part of something that is a force for good.

I’d like for Joyous to help millions of people have a better life giving them a real voice for change – whether that’s at work, as a customer, a citizen or in any context where their feedback can meaningfully help drive change for the better – both for themselves and others around them. In the next 2-3 years, if we can use our product and AI technology to normalize using feedback as an operating system for meaningful change rather than measurement – then I’ll feel seriously good about that.

What are the one or two accomplishments that you’re proud of?

Look, if you’d met super young Ruby, I don’t think you would have liked her much. My upbringing was rough and so was I. I’ve really turned that around, and in quite a deliberate way – I feel proud of that every day. My job is my passion, I work with great humans every day, doing something I really believe in. Then I get to go home and spend time with a rather wonderful family, living our best life. How could I not be proud of that?

What advice do you have for other up-and-coming technologists or leaders?

I would give this advice to anyone: Make a list. Make a list of the things that will make you happy. It can be anything from where you live, to the type of company you work for, to who you spend your time with – no limits to what this could look like. Then, systematically do the things that will make you happy. Nothing worth having comes easy. Everything takes a lot of deliberate thought and effort. If you do that, and do it regularly, say once a year, then – regardless of whether you’re an engineer, leader, mother or student – your life has a much better shot at being a good one.

I am active on LinkedIn where I have a few thousand followers now, otherwise not so much. I’m not trying to grow a following so much as I’m trying to write some content (through my blog and the books I write) that is helpful to people. I share that content on LinkedIn and also on our website – https://www.bejoyous.ai.

Who was your biggest influence?

I feel like I am the product of all the great people I’ve met – of which there have been many. Over time I’ve seen little things that I’ve really liked about others and tried to incorporate it into who I am. My aunt is a standout; she’s a professional with two children who has made a lot of time for me. She’s tough as nails, loves hard and will take a bullet for the people she loves. I think I’m a lot like her.

What is the most challenging part of your work as a Tech Executive?

People who are not in tech-startups – particularly in the AI space may not realize how much sheer persistence and grit is required to will something significant into being. And then again to create enough awareness and momentum for it to take-off. It’s both challenging and yet also the reason why I love what I do. I wouldn’t change a thing.

What do you have your sights set on next?

Eye on the prize with what we’ve got going on right now at Joyous. We sometimes joke we’re going to buy a remote island once we’ve made it and create a Joyous resort, mainly for ourselves to continue to live on as a community. Either that or I’ll try and debut as a comedian on my own Netflix show, working title: “Women aren’t funny.”

What is a day in your life like?

I am based in New Zealand. It’s a wonderful place full of nature, fabulous restaurants, a rich and diverse culture and more vineyards than I can visit.

I usually wake up around 6am, grab a filter coffee from our drip-machine and hop on a call with Katy – she’s the COO of Joyous and one of my closest friends. She’s on the other side of the world – usually grabbing lunch at this point over in Texas. We’ll chat about all things Joyous while I get my two kids ready for school, this often involves some low-grade yelling on the sidelines. I’ll also call a few other team members who are US based and at some point my husband ships my kids off to school and then I’ll have a shower and start some deep work. Either from home or I’ll drive to our offices. I really like to personally produce something for a couple of hours a day.

From there no two days are the same. I work hands-on across the business alongside the rest of the team, most often in Product, Data Science, Sales or with customers. For those of us based in Auckland our office is near the ocean and we like to sit by the water while eating lunch. Most nights at home end on the couch curled up with my kids watching a movie. Once the kids are asleep I’ll watch the most mindless TV Series I can find, either that or I’ll chat to someone from the team in Europe as they start their day. I also travel reasonably often – both for work and with family.

Do you have any hobbies?

I enjoy creative writing, reading, interior design, travelling. I recently did some improv too. One of my favorite past-times is designing swag for the Joyous merch store – we have definitely got the coolest clothing brand of any tech outfit. Hands down. https://www.bejoyous.ai/merch.

What makes you smile?

My 6-year-old daughter, who is funnier than I ever was.

What are you never without?

Underwear.

What scares you?

Not much honestly. I don’t like where the world is headed in terms of war. I’d like people to be kind to each other.

What is your favorite vacation spot?

I’m a sucker for a tropical island holiday. So probably Fiji, Rarotonga or our local vineyard island here, Waiheke.

Other work, published articles, interviews, or accomplishments:

FREE Trial: https://www.bejoyous.ai/try
Qualtrics trade-in: https://www.bejoyous.ai/trade-in/qualtrics

Podcasts

Blog Posts:

Books:

~ Ruby

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