Fostering Trust in Technology: Lessons for the Future

 Inside Jason St-Cyr’s Journey of Tech & Community
 

Jason St-Cyr is an accomplished leader in technology and digital marketing, currently serving as the Vice President of Engagement at Fishtank Consulting. With over 20 years of experience, Jason’s career has taken him through a wide array of roles, from software development and technical architecture to leading developer relations and community engagement. Known for his commitment to continuous improvement, Jason emphasizes building trust and driving strategic growth through educational initiatives and innovative engagement strategies.

A multiple-time recipient of the Sitecore MVP award, Jason has built a reputation for his hands-on approach, community-oriented mindset, and passion for creating meaningful, lasting connections with both developers and clients. His philosophy, “If you light a lamp for someone else, it will also brighten your path,” reflects his dedication to uplifting others through honesty, kindness, and helpfulness. He continues to be a thought leader in community building, often sharing his insights on digital experience management and customer engagement.
 

INTRODUCTION

In today’s interview, we’re excited to delve into the journey of Jason St-Cyr, a technology and marketing leader who has built a career on fostering genuine connections and driving impactful change in the digital experience space. From his early days as a developer to his current role as VP of Engagement at Fishtank Consulting, Jason has navigated the evolving landscape of tech with a hands-on approach and a community-centered mindset. Known for his emphasis on transparency, kindness, and continuous improvement, Jason shares his unique insights into leadership, the role of AI in customer education, and the importance of trust in building strong, lasting relationships. Join us as Jason reflects on his career journey, his achievements at Sitecore, and his vision for the future of digital engagement.
 

From Developer to VP of Engagement at Fishtank Consulting, your career journey is remarkable. What inspired you to transition from a technical role into more leadership and engagement-focused positions?

Jason: Back when I was a developer, what I loved most was building things. That excitement of learning and creating something new every day kept me going. Eventually, I moved into a leadership role in R&D, but I realized management wasn’t quite the path I wanted at the time; I wanted to stay hands-on. So, I pivoted into consulting, diving into Sitecore and digital experience platforms, which was a whole new world for me.

As I got deeper into Sitecore, I saw the community side of it. When a colleague won the Sitecore MVP award, I thought, ‘I want to do that!’ That’s when I began sharing my learnings—writing, creating code snippets, and later doing videos. This shift to community-focused work eventually led me to developer relations, which combined my love for content creation with helping others.

Over time, I found myself more drawn to the idea of leading teams that could build connections and help others. It’s incredibly rewarding to see others succeed and grow. I have a quote behind my desk that says, ‘If you light a lamp for someone else, it will also brighten your path.’ That’s been my guiding principle as I work on building meaningful, lasting connections, both for our teams at Fishtank and for our clients with their customers.
 

You’ve achieved significant success in growing Sitecore’s YouTube audience and developing the Developer Portal. Can you share some insights into how you approached these challenges and what contributed to their success?

Jason: For the YouTube channel and the Developer Portal, we had different strategies. With YouTube, I believed consistency was key. We aimed to release a helpful video every week for about six years, focusing on building trust through reliable content. Of course, not every video was a hit, but the goal was to be there regularly for our audience, creating a dependable resource.

The Developer Portal was a different challenge. Sitecore had recently acquired several companies, which left our resources scattered across various platforms. 

Developers and customers had a hard time finding what they needed, so we wanted to create a single, seamless experience. We focused on understanding the specific problems users faced and designing a straightforward flow to address them. Our approach was to launch with core features timed around a big event, ensuring we had a solution ready when demand peaked.

We also saw a major boost by inviting other teams to contribute, which brought even more users into the portal. This collaboration helped centralize resources and boosted adoption as more internal teams and audiences found value in the platform. Those were probably the two biggest factors in the success of both projects.
 

Sitecore Symposium 2024, which happened from October 15-18 in Nashville, Tennessee, was a major event for digital professionals with a focus on digital experience management and optimization. Could you shed some light on how digital experience management and optimization is evolving within the Sitecore ecosystem? Are there more big Sitecore events coming up this year or next?

Jason: I'm hoping we’ll see some of the SUGCON community events return next year. These are run by communities across India, Europe, and North America, and they’re great because it’s all about community members sharing insights with each other. The discussions and stories from those events are always valuable.

As for Sitecore Symposium this year in Nashville, AI was a big focus. Everyone’s excited about how AI can improve marketing workflows, but it still has to deliver value in ways that feel authentic and efficient. Right now, if you ask a tool like ChatGPT to create a social media post, it often misses your brand’s voice. So, at the Symposium, there was a lot of emphasis on how AI could be trained to understand your brand, utilize your content library, and ultimately help teams work faster without sacrificing quality. It's about optimizing the content creation flow so marketing teams can quickly create experiences tailored for specific audiences. Sitecore made a major announcement around their new offering Sitecore Stream that would help improve this flow across all their products.

Looking beyond the Symposium, I think we’ll see a lot of user groups picking up on what’s shared there, with members around the world discussing and sharing insights. These smaller, localized events help the community dive deeper into the latest updates and innovations, and they’ll probably pop up over the next year. At Fishtank, we went all-in for the Symposium—we sponsored the event, and our team was in Nashville connecting with everyone. They had a real blast and folks really enjoyed our snack-themed experience. We’re also planning some direct-to-audience webinars afterward to share our learnings and connect with our audience on a more personal level.
 

You’ve received the Sitecore MVP Technologist award multiple times. What does this recognition mean to you, and how has it shaped your approach to technology and community leadership?

Jason: When I first received the award, it was incredibly rewarding because I’d worked hard to create helpful content and support the community. But over time, I realized that if you’re only doing it for the award, it’s the wrong motivation. I always tell people aiming for the award that you have to genuinely enjoy what you’re doing—whether it’s writing, creating videos, or speaking at events. If you’re driven by a passion for helping others, recognition will naturally follow. But if you’re forcing it just for the title, it won’t be sustainable.

In the community, the MVP award does carry weight professionally. It can lead to career growth, higher salaries, or new opportunities. So, for anyone who’s part of the Sitecore community, I’d say go for it! Apply, put in the effort, and don’t be discouraged if it doesn’t happen right away. The worst that can happen is you’re encouraged to try again next year.
 

At Fishtank Consulting, you’re focusing on enhancing educational offerings and deepening client engagement. How do you envision the future of customer education in the digital experience space?

Jason: If we think back to when Google first appeared, it changed the way companies created educational content. Everyone started focusing on articles, videos, and webinars that would rank well on search engines, driving traffic to their sites. For over 15 years, that’s been the go-to approach.

But now, things are shifting. People are turning to chatbots and AI interfaces instead of traditional search, and these models are pulling in content from across the web without necessarily directing traffic back to the original sites. This means brands aren’t getting the same brand recognition they used to from their educational content.

I believe we’ll see companies trying to get their content into these AI channels while still keeping their brand visible. It’s similar to how Google eventually introduced promoted keywords. Right now, AI companies are operating at a loss, but there’s potential for a business model that lets brands tap into AI-driven visibility.

At the same time, I think we’ll see a counter-movement, with people gravitating toward smaller, community-driven spaces—like gated communities or private networks—where individuals share content within a more personal network. Platforms like Reddit are already pushing back against AI scraping, so we may see this dual evolution: brands finding ways to gain visibility in AI channels and communities creating tighter, more exclusive spaces for content sharing.
 

As someone who emphasizes continuous improvement, how do you maintain a balance between driving change and staying grounded in the core values of honesty, kindness, and helpfulness in your leadership roles?

Jason: For me, continuous improvement means focusing on smaller, manageable goals so teams can see value from their efforts sooner. I prefer short cycles where teams work on a single task, deliver something meaningful, and then build on that. This approach helps us avoid investing months of work that might become irrelevant if priorities shift. By working in smaller chunks, we also reduce mental strain, keeping the team focused on what’s most important in the near term.

I don’t think continuous improvement conflicts with core values like kindness and helpfulness. In fact, breaking work down into achievable steps gives team members regular wins and creates a more supportive environment. Plus, working in small iterations means we’re learning constantly, which keeps us in a cycle of growth. Whether we succeed or fail, each step brings lessons we can share and build on.
 

What advice would you give to emerging leaders in the tech industry who want to build authentic and lasting relationships with their communities and customers?

Jason: If I had to give one piece of advice, it’s this: focus on building trust. In today’s world, where there’s so much misinformation, trust has become incredibly valuable. I believe trust is built on three things: honesty, kindness, and helpfulness. Being transparent builds credibility, kindness shows empathy, and being helpful creates positive associations. When people see you as someone who genuinely wants to help, they’ll remember that and turn to you when they need support.

It’s essential to connect with people on a human level. Even if you can’t solve every problem, listening and showing you care builds a strong foundation. The real challenge is doing this at scale—how do you build that same trust and connection with thousands of people? That’s where digital experiences come in.

Building these connections may sound idealistic, but it does have a real payoff. I’ve seen it myself. When I faced tough times, people I’d connected with over the years reached out to support me. It was a powerful reminder of the value of those relationships. My advice to emerging leaders is to invest in these connections now; they’ll come back to support you when you need it most.
 

Conclusion

Jason St-Cyr’s journey exemplifies how a commitment to community, trust, and continuous improvement can drive meaningful impact in the digital experience space. His insights provide valuable lessons for anyone striving to lead with authenticity and build lasting connections in the tech industry.