From Oil Fields to Gaming Gold: How Jess Leonard Became Gamesight's "Head of Vibes"
In an industry where burnout rates soar and company culture often takes a backseat to rapid growth, Jess Leonard has carved out something extraordinary. As the self-proclaimed "Head of Vibes" at Gamesight.io, she's transformed what could have been just another high-pressure startup into a workplace that's earned recognition as a Best Place to Work by GamesIndustry.biz for two consecutive years—all while helping the company increase its monthly recurring revenue per employee by an impressive 132%.
Leonard's journey to gaming leadership is anything but conventional. After spending a decade building expertise in title research and petroleum operations, she made a bold leap into the startup world, joining Gamesight as its first Chief of Staff. In just 18 months, she witnessed and helped orchestrate a three-fold expansion in headcount before evolving into her current role as Director of Operations.
What makes Leonard's approach unique isn't just her unconventional background—though her experience in resource-intensive industries certainly informs her talent for optimization and efficiency. It's her philosophy that successful organizations require both analytical rigor and genuine human connection, a principle that mirrors Gamesight's own "heart + data" approach to performance marketing.
In our conversation, Leonard opens up about navigating the transition from traditional industries to gaming, the real-world strategies behind building scalable team culture, and why she believes that in a sector obsessed with metrics and KPIs, the most important measurement might just be how people feel when they come to work each day.
You transitioned from a decade in petroleum operations to the fast-paced world of gaming startups—what inspired that leap, and how did you adapt your skillset to such a radically different industry?
Believe it or not, petroleum operations wasn't what I set out to be when I grew up. I went to university to be a history teacher, like my step-dad, and fell into the oil & gas gig through a friend. A history major is well suited to do the in-depth, detail-oriented analysis needed for ownership research and curative work, to say nothing of getting to travel to isolated courthouses and look at deeds from the 1700s. I pivoted out of the energy sector because it wasn't something I was passionate about. And the adaptation wasn't as radical as you might think. Operations is, broadly, operations. Whether acquiring millions of acres of leases or building new onboarding processes, it's about creating efficient systems, managing resources, and enabling teams to do their best work. The speed was definitely different. In oil and gas, projects span years and work comes and goes with the economy; in influencer marketing and startup SaaS, we iterate daily. That's something I had to adjust to.
As Director of Operations, how do you balance creativity and data when building internal systems and culture at Gamesight?
We try to borrow from game mechanics where we can and meet our team members where they are or where they are comfortable. We've tried to make career progression feel more like "leveling up" and less like bureaucratic box checking, but the concept is easier to dream up than it is to execute. That being said, one of Gamesight's principles is "Data is Our Magic," so it's essential for any quests (surveys) to be used or created in a data-driven way. A good example is the wild volume of Gamesight swag we have created over the years - some more off-the-wall than others. We recently ran a quest to get better insight into what items or apparel people would prefer we slap our internal memes on, so hopefully, they find those items useful and worth having, even if the design is uniquely Gamesight. Essentially, we have tried to preserve some of the creative chaos that is innate to what Gamesight is, while creating operational buffers to keep people progressing in the right direction.
You’ve described your work as playing a real-life 4X game—can you share a moment where strategic planning and team coordination led to a major operational win?
Our annual all-hands in-person company retreat is absolutely a 4X game. Despite being a team of only 50, we start planning the following year's offsite about a week after the current one wraps. Our offsites are very bespoke, it's easily one of my favorite things we do at Gamesight. They involve a lot of custom 3D printed trophies, unique prize pools, individualized superlatives for every employee, and last year, we added a competition, similar to Beast Games, that runs over all three days of the offsite. If we use Sid Meier's Civilization as a parallel here, the project is definitely phased into early, mid, and late game, and each era has its own success metrics. We obviously have finite resources, so where are those being used, and where can we double-dip into resources we already have on our continent, if you will? Offsites also require a lot of diplomacy, whether you are going for that victory type or not. You need to consider each team's preferences and goals and sometimes make trades to get the alliance across the finish line. I could go on…but I'll stop while I'm ahead.
Gamesight has seen impressive growth and accolades under your leadership—what are some less-visible but critical changes you implemented that helped enable that success?
We are diligent about getting rid of things that aren't working. For example, in the past, we tried using several different project management tools. The extra work of nagging people to use them, combined with the effort it took to keep them at a level of accuracy that made the data contained therein ANY amount of useful, was a nightmare. It wasn't worth it. Now we use Slack's new lightweight project management tools, and people have adopted those at a much higher rate - it's an easy-to-use software nested in the place where they spend most of their work day. Many of our team members also value their own time enough to spur people to templatize and automate where we can. No one wants to do the same tedious tasks over and over again, and usually, they don't have to. Slack Workflows and Automations are handy here, too.
What advice would you give to women looking to pivot into tech leadership roles, especially those coming from non-traditional or unrelated industries?
I would say to take a look at your values and lean on those. If your top five values are family, traveling, humor, transparency, and creativity, those are your superpowers. How do those show up in the work you do now? How do you imagine they'd show up in a different industry? If you aren't sure how those values will be useful, reach out to people in similar roles or with similar career pivots and ask for a coffee chat. People are, by and large, generous with their time and knowledge if you ask. And use AI responsibly where you can - ask ChatGPT or Claude to interview you for a position you'd like to have one day, and start looking for examples of success from your current work that make you feel confident in your abilities to be successful elsewhere.
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