CEO Insights Magazine

Jordan Kastrinsky

Managing Partner

The world has never been more open to entrepreneurship and innovation, but it has also never been more demanding. Succeeding as an entrepreneur today requires more than just ambition. It calls for self-motivation, a clear vision, and the courage to take calculated risks. For those who feel called to lead, the reality is that time won’t wait, and the pace of the world isn’t slowing down. The boldest leaps may involve risk, but they also carry the potential to create something lasting, meaningful, and truly transformative.

Jordan Kastrinsky reflects this mindset. As Managing Partner of Global Upscale, he has spent several years helping businesses grow and evolve through a distinctive blend of creative strategy, operational insight, and entrepreneurial drive. From his early start in video production to launching a digital agency during a global pandemic, his journey is testament to what is possible when passion, purpose, and perseverance combine. What drives Jordan, beyond the desire for ownership or impact, is the ability to directly influence the success of the businesses he works with.

In this conversation, Jordan shares his growth story, leadership philosophy, and his vision for the future of entrepreneurship, innovation, and digital transformation.

Share a glimpse of your professional growth story.

My professional journey began while I was still at university, where I pursued a multidisciplinary degree in linguistics and video production. At the time, I found myself drawn to entrepreneurial endeavors, taking on freelance work in videography and video editing. It was more than just a side hustle, it was the beginning of a mindset.

After graduating, I joined the Israeli army and served in a media communications unit, which allowed me to continue honing my creative and technical skills while still freelancing and building client relationships.

That period gave me both structure and momentum.

Following my service and a brief stint in the private sector, I co-founded Global Upscale during the COVID-19 pandemic after a timely and serendipitous meeting with my current business partner. I’ve spent the past five years helping companies reshape their digital presence and expand into new markets.

Entrepreneurship, for me, is a continuous process of building, testing, and iterating, with the goal of not just growing my business, but also contributing meaningfully to the success of others.

What do you consider when tailoring your offerings to clients?

When suggesting offerings to clients, I always start by trying to understand their real objectives, not just the tactics they're asking for, but the underlying business goals they're trying to achieve. It's easy in this industry to get excited when a client mentions a budget or rush to recommend popular solutions. But I believe that the real value lies in stepping back and asking the right questions. What is the client truly trying to accomplish? Do they have the foundation in place to support that effort? For example, if a client comes to us with a $10,000 budget for Google Ads, but they don’t have a website, social media presence, or any historical campaign data, then the budget is likely to be misallocated.

In those cases, I explain that jumping straight into paid advertising without a larger strategic pipeline might not yield the results they expect. So, instead of simply delivering what they ask for, I aim to partner with them, and make sure the solutions we recommend are aligned with their broader vision.

What is your leadership style and approach?

As a leader, my approach is built around two core principles, namely clear communication and consistent engagement.

First and foremost, I prioritize setting expectations early and clearly. I make a strong effort to communicate my goals, standards, and desired outcomes from the start. In my experience, one of the most common causes of misalignment is when a team member assumes what’s expected without having been clearly guided. If something doesn’t go as planned, I see it as a reflection on my communication, not just on their execution.

Secondly, because we operate as a fully remote agency, I prioritize regular contact with my team, not micromanaging, but staying present through daily check-ins to ensure priorities are clear, remove blockers, and offer support.

How do you stay updated on industry trends?

Given how rapidly things evolve in marketing, design, and business development, I believe staying current isn’t optional, it’s essential. The rise of AI and emerging technologies has only accelerated this pace, so I make a concerted effort to stay ahead.

I actively follow a curated set of newsletters focused on marketing, design, and tech innovation, along with global business news to understand the broader economic and cultural shifts. When I come across a new platform or company, I go beyond just reading about it. I dive in, watch demos, test tools, and assess how they’re positioning themselves in the market. I also sign up for trials to explore functionality hands-on. If something proves useful, we integrate it internally. If not, it still adds to my understanding of where the industry is heading.

What is your future destination?

As AI tools continue to advance, I believe the long-term value at Global Upscale will lie in our human-centered approach, one that emphasizes understanding people, building authentic relationships, and applying strategic thinking to solve complex business challenges.

This philosophy aligns closely with our founding vision. When we launched Global Upscale as a hybrid between marketing and business development, the goal was always to offer more than just execution. We aimed to be strategic growth partners. Now, we're leaning back into that original methodology with renewed focus, helping businesses scale intelligently and sustainably.

As we grow, I envision Global Upscale evolving into a startup factory, an internal ecosystem that incubates and launches ventures, either independently or in partnership with entrepreneurs. We've already explored models like equity-based and design partnerships, and I’m eager to refine these approaches to provide support to the early-stage ideas we believe in.

On a personal level, I recently completed a Master’s in Cybersecurity and plan to integrate its principles with digital strategy and business development to future-proof our offerings.

Jordan Kastrinsky, Managing Partner, Global Upscale

Jordan Kastrinsky is a multilingual marketing and business development leader who assists businesses worldwide in their digital transformation, crafting successful marketing campaigns.

Hobbies: Boxing, Running, Yoga, Hiking, Cooking Watching movies

Favourite Cuisine: Italian, Mexican, Indian

Favourite Book: Robert Green's 48 Laws of Power, Viktor Frankl Man's Search for Meaning, The Lord of the Rings Book

Favourite Travel Destination: Italy, India

Awards & Recognition:

Channel 14’s Top 75 Young People to Watch in honor of Israel’s 75th Independence Day (2023)

Global Upscale recognized with the Tech Behemoth 2024 Award for Top social media and WordPress Agency in Israel

Host of the "High Tech on the Low" podcast, featured in Geektime, New York Tech Media, MSN, and House of Ventures