Thank you so much for joining us in this interview series. Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?
Absolutely, happy to be here!
My story began when I swapped the predictable path of business school for the unpredictable world of software development in Silicon Valley. It was an exciting time, right before the dot com bubble, where I really cut my teeth on the possibilities of open source technologies for major brands. This foundational experience was transformative, and eventually, I felt a strong pull to bring that energy and innovation back to Canada.
That’s when I founded the Vancouver International Bhangra Celebration, an event that grew to attract thousands annually and became part of the cultural festivities during Vancouver’s 2010 Winter Olympics. These experiences deepened my appreciation for cultural expression and community impact, guiding me towards a more integrated approach to technology and the arts.
As my career evolved, I ventured into brand development and creative strategy, working with major brands to refine their digital presence. In 2011, I founded Skyrocket Digital, a catalyst for change that focuses on helping companies navigate their digital transformation journeys. I get to work closely with a diverse range of clients, helping them create digital experiences that resonate with their audiences.
Alongside my professional work, I co-founded the Poetic Justice Foundation to advocate for social change and challenge structures of oppression. This work is incredibly important to me, allowing me to use my platform to support intersectional advocacy and create meaningful change.
Through all of this, my goal has always been to harness technology and creativity to break down barriers and build inclusive communities. Each step of my journey has taught me more about the power of connecting with others and making a positive impact, and I’m excited to see where it will lead next.
Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?
When I was just starting out, I was so eager to get things moving that I partnered with practically anyone who shared my enthusiasm, without properly vetting them. Let’s just say I ended up with a mix of what I call ‘effective arseholes’ — brilliant minds but a nightmare to work with.
That was an eye-opener for me. I learned pretty quickly that having the same values and cultural alignment is just as crucial as having the skills. It’s not just the big decisions that shape your path, but also the zillion little ones made day-to-day, and those are all about alignment. When everyone’s on the same page, things just flow; decisions feel right and happen smoothly. This early headache taught me to weigh cultural fit as much as, if not more than, pure skill. It’s reshaped how I pick who I work with and build my teams — it’s all about the fit and shared values now.
None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful for who helped get you to where you are? Can you share a story?
As I’m thinking about how to answer this question, the list of people I’m grateful for kept growing. Then I realized that as much as it may have been particular people at different stages in my journey, it’s really been a community of people that have wanted to see me succeed that have gone out of their way to open doors, make connections and invite me into spaces that would have otherwise been inaccessible. I’m surrounded by generous people.
Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?
‘Good to Great’ by Jim Collins is at the top of my list because it distills what differentiates good companies from those that achieve great levels of success. The idea of the ‘Flywheel’ and ‘Level 5 Leadership’ really resonated with me. They drill into how true leaders operate — quietly powerful, relentlessly pushing forward without needing a spotlight. It’s all about that slow build, which plays into how I think about growth — like layering one small win on top of another until you’re suddenly flying.
Anything written by Malcolm Gladwell has left a mark. ‘Tipping Point’ and ‘Outliers’ show how tiny things, things you’d never think twice about, can snowball into big, market-shaking trends. It makes you look at the small details differently, spotting potential where others might not see anything.
‘Dune’ by Frank Herbert has also been significant for me. It’s not just a science fiction novel; it’s a study on the complexities of power, ecology, and human motivation. The way he exposes human complexity in his stories, that’s how I see business ecosystems — these are timeless human dynamics. Every piece matters, everything’s connected, and the whole machine pivots on both the massive and the microscopic.
Lastly, ‘The Dawn of Everything’ by David Graeber and David Wengrow radically shifted my perception of human history and societal development. This book turns the whole ‘how we got here’ story on its head, challenging the straight-line narrative we’re so often sold about human progress. It’s a wake-up call to think bigger, question deeper, and imagine a wilder range of possibilities for how we organize and drive forward. It’s like a playbook for how I approach shaking things up with digital transformation — never just accepting the ‘this is how it’s always been done’ but always poking at it, twisting it, and seeing if there’s a better, smarter way to move forward. Imagination works both forwards and backwards.
Are you working on any new, exciting projects now? How do you think that might help people?
This feels like a really mundane answer, because AI is all anyone in tech is talking about right now.
While everyone’s talking about AI, I’m digging deeper into what really excites me: how AI isn’t just a trend or a fancy gadget — it’s about redefining the partnership between humans and technology, making it a true collaboration that pushes boundaries and rewrites rules
AI shouldn’t be looked at as just another tool; it should be looked at as a co-pilot who helps navigate through the clutter of routine tasks and mental blocks. It’s about using AI to supercharge our natural abilities, helping us jump higher and run faster, metaphorically speaking. It makes tackling complex problems smoother and turns daunting tasks into manageable ones.
Think about our usual daily hurdles — procrastination, the overwhelming blank page, the psychological drain of starting from scratch. Now, imagine having a companion that’s built to complement and enhance your strengths, always ready to assist, refine, and push forward.
For example, I really hesitate to use people as a sounding board. It can feel like a selfish exercise, constantly bouncing half-baked ideas off others. But here’s where AI changes the game. It acts like a spitballing engine, a sounding board that’s always available, never judges, and helps you clarify your thoughts. It’s like having a brainstorming partner who’s in it just for you, ready to help you refine and evolve your ideas without any reservations.
With this experiment, it’s not just about streamlining processes; it’s about expanding our capacities and elevating our potential. I’m excited to see how this will unlock new levels of creative expression and intellectual exploration. It’s about digging deeper into ourselves, discovering potentials we hadn’t tapped into yet — part power, part intellect, all geared towards making us better at being ourselves.
For me, AI isn’t just tech, it’s innovation — it’s a reimagining of how we interact with technology, transforming it from a tool into a teammate. That’s the game-changer I’m focused on — turning AI into something that doesn’t just compute, but collaborates, creating a whole new way to amplify what we can achieve.
Thank you for all that. Let’s now turn to the main focus of our discussion about Digital Transformation. Digital transformation can mean many things to many people, from your perspective, how do you define digital transformation in your industry?
When most people think about ‘digital transformation,’ they’re thinking software upgrades, new systems, maybe a shiny app or two. But, it’s so much more than just slapping some new tech on an old problem.
Digital transformation is really a precursor for a massive cultural shift. It’s not just about the tools we use; it’s about how we use them to change the way we work together, how we think about problems, and how we drive companies forward. Think of the tech as just the ingredients. What we’re cooking up is a whole new way of operating — a recipe for working smarter, not harder.
So, in my world, it’s not just a digital transformation; it’s a transformation of everything we know about work. It’s about making processes more seamless, teams more integrated, and insights sharper. We’re not just changing the software we use; we’re changing the game itself. And that, to me, is what digital transformation is all about — it’s a cultural shift disguised as a tech upgrade.
Which companies can most benefit from a Digital Transformation?
My immediate instinct is to say that every company can benefit, but particularly those that feel like they’re stuck or lagging behind their potential. For instance, large enterprises often suffer from ‘process calcification’ — where systems are so layered and rigid that they inhibit flexibility. Digital transformation can reintroduce that agility, allowing companies to be more responsive and innovative.
It’s a bit like spinach; it’s good for everybody, but it will immediately help those who are the unhealthiest.
Companies that have lost their flexibility and responsiveness due to outdated processes stand to gain the most by adopting new digital strategies. They see the fastest and most dramatic improvements when they start to incorporate these transformative technologies.
If you don’t rise to the level of your aspirations, you fall to the level of your systems. This emphasizes the need for robust, adaptable systems that can truly elevate a company’s operations to match its ambitions.There are very few industries, if any, left that this wouldn’t be beneficial for.
Has integrating Digital Transformation been a challenging process for some companies? What are the challenges? How do you help resolve them?
Change. Is. Really. Hard.
Integrating digital transformation is challenging for most companies, because it disrupts established ways of working. One of the biggest hurdles is the natural resistance to change. People get comfortable with familiar processes, and even if those processes are inefficient, the unknown can be intimidating. This discomfort is magnified by the fact that, during the transition phase, there’s often a dip in productivity, which can cause tension and resistance among staff.
At Skyrocket Digital, we take a very hands-on, empathetic approach. The key is spending time with the people who will be affected by these changes. It’s about understanding their workflows, their concerns, and their aspirations. This understanding allows us to tailor the transformation process to fit the unique culture and needs of each organization. We aim to get everyone not just on board, but excited about what the new systems and processes can do for them.
For example, one of our key strategies is treating digital transformation as an iterative process. Instead of rolling out massive changes all at once, which can feel like a car wreck, we implement small, manageable changes over time. This approach reduces the impact on daily operations and helps people adjust more gradually. As they start seeing the benefits of each change, their buy-in and enthusiasm grow, easing the transition to larger transformations.
Sometimes, when proposing radical changes, we create isolated ‘sandbox’ environments where new systems can be tested without affecting the entire operation. This low-risk, low-investment approach allows the team to experiment and see the potential benefits without the pressure of having to commit to a full rollout immediately.
Managing change is not just about introducing new technology; it’s about aligning with the people and guiding them through the transformation. We focus on elevating everyone’s understanding and capabilities alongside the system enhancements. By managing the process thoughtfully and strategically, we help companies not only adopt new technologies but also embrace a new culture of innovation and efficiency.
Based on your experience and success, what are “Five Ways a Company Can Use Digital Transformation To Take It To The Next Level”?
1 . Break down Silos and Remove Barriers.
We helped our client Ocean Wise, an ocean conservancy working on the preservation of our planet’s future, move from paper and spreadsheets to a new custom web app built atop of Salesforce. The tools are less important, but the fact that various departments now work “through” the application means that data collection and reporting is real time, while bringing efficiency to the daily lives of the program managers working to improve the health of our oceans.
2 . Create a New Culture
Any big shift in an organization’s operation must be supported by a shift in behaviours, as well — new ways of doing and thinking the same things that many team members have likely been doing for years. So, use this as an opportunity to shift and evolve the culture as well. Recruit people into a new vision for the operations, reinforce that vision early and often. CarSimple had been in the car sales business for decades through traditional dealerships. Building up to the launch of their new direct-to-consumer experience, they used the development of the new used car sales platform as an opportunity to create excitement across their traditional dealerships, and then revisited their overall operations to begin unifying departments and systems in their legacy businesses.
3 . Real Time Data for Decision-Making
Regular business operations rely on month-end and year-end activities to develop a clear picture of the previous period and consolidate operational metrics and financial data. Data transformation can provide a unification of workflows and metrics, so that business operations can move from batch reporting to real time dashboards. When the Self-Realization Fellowship out of Los Angeles would collect their impact data, it often meant going to multiple departments to cobble together sales of literature, digital media, event attendance and their annual convocation of kriya yoga graduates. A new consumer-facing website with better integration to back end systems, virtual events and sales channels meant that impact data was now a live feed rather than an annual reporting activity.
4 . Improve Your Team’s Experience
Most people working in an ambitious organization are there to make an impact. Often in large enterprises this means that people get very efficient at finding their way through high friction, inefficient systems and workflows. By taking the time to understand the process of value creation, and the journey of your employees as they work to deliver that value, you can not only improve processes, but also improve the experience of the people doing the work. This has the potential to increase the impact and wellbeing of every team member.
5 . Accelerate Responsiveness.
Digital transformation isn’t about applying a new coat of paint on dated systems, or layering fancy new tools on top of legacy systems. Digital transformation is a holistic approach to the entire operation, while balancing engineering investments with ROI. The outcome of this should be less internal complexity and lock-in with particular solution vendors. The rate of technological change is only going to increase, so the digital transformation process should make every enterprise more nimble and adaptable as a result.
In your opinion, how can companies best create a “culture of innovation” in order to create new competitive advantages?
Innovation is messy, unpredictable, and in hindsight, quite fascinating. You don’t wake up one day and decide, ‘Today, I’m going to innovate.’ It doesn’t work like that. It’s more about embracing the weird, the quirky, the unexpected. It’s about getting knee-deep in curiosity — exploring, researching, and sometimes just bumbling around.
Actual innovation is hard. It’s not something you realize you’re doing until you look back. One day, you’re just tinkering around, following some bizarre hunch, or pulling on a thread that everyone else seems to have ignored, and then, sometime later, you turn around and go, ‘Wow, that was actually pretty groundbreaking.’
That’s why creating a culture of innovation isn’t about forcing out big ideas; it’s about cultivating an environment where it’s okay to be curious and a bit unconventional. Set aside resources — that’s important. But give people time and space to chase down their crazy ideas without the immediate pressure of a deadline or ROI. Most of all, give them permission to be different, to think differently, and to fail.
And here’s another thing: recognize the value of these odd explorations. Celebrate the strange paths people take, because sometimes, those weird, winding paths are where the magic happens. It’s in the afterglow, looking back, that you realize, ‘Hey, we were innovating all along!’
Encourage exploration, tolerate the mess, and nurture the quirks. That’s how you stumble upon innovation — it’s not always shiny and sleek from the get-go. Sometimes it’s just a weird little side project that blew up into something amazing.
Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?
‘Damned if you do, and damned if you don’t.’
There’s something liberating about acknowledging that no matter what you do, you can’t please everyone, and you’re going to ruffle a few feathers either way.
In my line of work — and in life in general — you come across a lot of decision points. And at each one, you’ll find plenty of reasons to go one way or another. You can drown in the pros and cons if you let yourself. But the real risk isn’t in choosing one path over another; it’s in not choosing at all. I’ve learned that you’ve got to take the leap, make the call, even if it means facing some heat. Because at the end of the day, if you’re going to catch flak either way, you might as well do it chasing after what you believe in.
This way of thinking has been my north star when making tough calls, pushing boundaries, and even forging ahead with ideas that seemed a bit wild at the time. Because if we’re all going to be ‘damned’ one way or another, why not be ‘damned’ while creating something great.
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Thank you so much for sharing these important insights. We wish you continued success and good health!