Roshni Wijayasinha Of Prosh Marketing On How To Succeed By Doing Things Differently

An Interview With Chad Silverstein

We decided to actively participate in startup and small business ventures as a mentor and contributor to position ourselves as experts in the industry and gain a lead-flow that we can build relationships with. Our work with community partners has ensured a consistent flow of referrals.

In the world of business and within every industry, there are forward-thinking leaders who go against the status quo and find success. Their courage to take risks, embrace innovation, and inspire collaboration separates them from the competition. Until 2002, Apple’s famous slogan was “Think Different”. This attitude likely helped them become one of the most successful organizations in history. This interview series aims to showcase visionary leaders and their “status quo-breaking” approach to doing business. As part of this series, I had the pleasure of interviewing Roshni Wijayasinha.

Roshni Wijayasinha is a trusted leader with over 15 years of marketing experience, having launched over 50 products and brands in more than 20 markets worldwide and helped companies secure nine-figure investment rounds. Roshni founded Prosh Marketing, a Marketing Consulting practice specializing in strategy, planning, and communications for startups and SMBs.

Thank you so much for doing this with us! Our readers would love to get to know you a bit better. Can you tell us your “Origin Story”? Can you tell us the story of how you grew up?

I grew up in Ivory Coast, Africa, and later moved to Canada at the age of 7. My parents ran a business, and I often found myself in their workplace. I would wait at the printer for any spare or error paper and draw on it. As I grew older in Canada, I took on various roles in my parents’ business. Their encouragement led me to start my own art and piano studio during my teenage years, where kids would visit my studio for lessons. As I attended art school, I wondered how to turn my creativity into a sustainable career. Eventually, I decided to pursue a career in marketing, a field that allowed me to unleash my creativity while also providing a stable source of income.

Can you give us a glimpse into your journey into this industry and share a story about one of the most significant challenges you faced when you first started out? How did you end up resolving that challenge?

My journey started with an unpaid internship at Cosette, a creative agency, where I had the opportunity to work on the Toronto Film Festival’s inaugural website. Later, I joined Canwest Global, an advertising agency, and became part of the interactive department, which is today’s digital marketing. This role onboarded me to the digital advertising and media ad space. I also had the privilege of working at Microsoft, as a member of the product team where I got to launch Windows Live Skydrive (now OneDrive) and work on Windows Live Today. My mentors there recommended I pursue an MBA to further my skills. However, I graduated during a recession, which presented significant challenges in my job search.

Overcoming all the challenges by aggressively applying to a wide range of marketing opportunities, I secured a position at Sony Mobile, where I launched the first camera phone in Canada. Breaking through into these new categories, we faced a lot of ambiguity due to the lack of information and references to the market. We conducted extensive research to best position our product launches. These experiences taught me to thrive in uncertainty, a valuable skill that is especially applicable now, when working with Startups.

Who has been the most significant influence in your business journey, and what is the most significant lesson or insight you have learned from them?

My dad remains my all-time role model, especially in my entrepreneurial journey. His commitment to his work has provided me with a vital lesson — the significance of hard work and the rewards it brings. He was a hands-on entrepreneur who was involved in every aspect of his business. Balancing work and a family was not easy, but his perseverance allowed him to still manage both, both in Africa and Canada.

Can you share a story about something specific that happened early on that you would consider a failure but ended up being a blessing in disguise or ended up being one of the most valuable lessons you had to learn on your own?

In the early days of Prosh Marketing, our positioning as marketing consultants didn’t quite resonate with the market, as businesses sought expertise that could execute marketing strategies. We made a pivotal shift towards a fractional CMO model, which combined strategy with implementation and coaching to empower businesses to enhance their marketing potential. This decision provided us a competitive advantage and a unique value proposition, as first movers in the startup market.

Leading anything is hard, especially when grappling with a difficult situation where it seems that no matter what you decide, it will have a negative impact on those around you. Can you share a story about a situation you faced that required making a “hard call” or a tough decision between two paths?

Choosing the target audience for Prosh Marketing was a tough decision — deciding whether we should target larger businesses or startups and small businesses, Ultimately, we opted for smaller, growing businesses as they value and need our part-time marketing leadership services the most — making the best product-market fit.

Let’s shift our focus to the core of this interview about ‘Successful Rule Breakers’. Why did you decide to “break the rules”? Early on, did you identify a particular problem or issue in how businesses in your industry generally operated? What specifically compelled you to address this and want to do things differently? Please share how you went about implementing those changes and the impact they had.

I observed that startups and small businesses often face budget constraints, being unable to afford or not requiring a full-time head of marketing with a small budget to spend. They need to scale rapidly and efficiently but must do so with junior marketers such as interns or marketing coordinators, as this is usually what their budgets can afford. The recognition of this gap led us to introduce part-time marketing leadership (Fractional CMOs) to be a cost-effective solution. Having been a VP of Marketing in a few startups, I knew the benefit a little experience could provide and so this motivated me to offer this at scale to more growing businesses.

In the ever-changing business landscape, how exactly do you decide when to adhere to industry norms versus “breaking the rules” and forging your own way? Can you share an example?

We paid attention to what our customers needed and identified the gaps in the market, which guided our decision-making. The fractional CMO model aligned with what customers wanted and the flexibility they required. Our approach of offering guidance and actively implementing marketing strategies allowed us to successfully stand out from the usual consulting firms or agencies.

What guidance or insight can you offer to new entrepreneurs trying to follow existing and accepted industry norms while at the same time trying to differentiate themselves in the marketplace?

I would say is to start small, test, and learn. Check to see how your market reacts and evaluate all relevant trends before putting all your eggs in one basket. Balancing your ideas with market needs, you’ll ultimately want to ensure you’re able to find a unique value proposition and competitive advantage, so don’t be afraid to take risks and be different.

Here is the main question of our interview. To make an impact, you have to champion change, get creative, and take risks. Please think back about the decisions you’ve made that have helped your business get to where it is today and share your top 5 strategies or decisions that helped you succeed by doing things differently.

1. Focusing on Startups and Small Businesses

We made the conscious decision not to target larger companies that could afford more, but smaller, growing businesses whose needs most aligned with our service offering, and therefore had a better product-market fit.

2. Adapting our Service Delivery Model

Prior to the pandemic, we delivered our services online. Adapting to a virtual service delivery model via video conferencing allowed us to not only sustain ourselves during the pandemic but significantly grow. We were able to service larger service areas where we had international experience (if the time difference could work) and cut our travel time (downtime) down too. This allowed us to increase our revenues by attracting new markets and increasing our margins.

3. Building Partnerships for Implementation

To truly specialize and provide exceptional service by focusing on what we’re good at, we made a decision to partner with other companies to help with marketing implementation vs. doing it ourselves. Here, we were able to create great relationships with other similar businesses who have become great referral partners for us as well. This has also allowed us to maintain clear positioning vs. being a jack of all trades. This has also resulted in better options for our clients who can select from a range of partners to find the best fit.

4. Marketing first, Sales later

Prioritizing inbound marketing has enabled organic growth for our business, credibility, and a reduction in business development costs — after all as a Marketing company, this is our area of expertise Given we’re B2B, developing that trust through marketing efforts was imperative, and leveraging word of mouth and referrals vs outbound sales has also brought in great quality leads. Finally, this strategy has also leveraged content marketing to educate customers to build a relationship with them so that they ultimately reach out to us when they’re ready for help.

5. Investing in Mentorship in the Community

We decided to actively participate in startup and small business ventures as a mentor and contributors to position ourselves as experts in the industry and gain a lead-flow that we can build relationships with. Our work with community partners has ensured a consistent flow of referrals.

As a leader, how do you rally others to align with your vision? Also, how do you identify those who may not be fully committed or even silently sabotaging or undermining your efforts? What steps do you take to address these situations?

Communication plays an important role in bringing people together and getting everyone on the same page. I usually begin by explaining our business vision, which is all about helping startups and small businesses. I aim to inspire others with my deep passion for marketing and these growing businesses and encourage them to find some personal enjoyment and fulfillment in what they do.

Regular check-ins and keeping an open dialogue are essential for recognizing any issues within the team. We also emphasize the value of approaching each other with kindness, which is one of our core principles. This fosters motivation to collaborate and generate creative and practical strategies. As for our interns, we’ve established a mentor-mentee relationship and a culture that encourages them to explore and learn in a positive and supportive environment.

Imagine we’re sitting down together two years from now, looking back at your company’s last 24 months. What specific accomplishments would have to happen for you to be happy with your progress?

I hope to have expanded our presence to more states within the U.S. and have formed an outbound business development team. This team will help us scale faster and allow us to onboard additional fractional CMOs across various industries, as well as clients.

You are a person of enormous influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

My vision would be to advocate for kindness in business. This would foster a culture where people prioritize positive personal interactions so that people feel cared for, valued, and seen. Internally, we all spend so much time in our work environments so a little kindness could go a long way in enhancing mental health and ultimately affect contentment/job satisfaction and performance.

When we look externally at clients, partners, vendors, etc. It is also important to practice kindness.

Sometimes, startups and small businesses approach me for marketing advice with extremely limited marketing budgets. In many cases, I’m willing to dedicate time to have a conversation, share some quick insights, and offer suggestions that can help them thrive and grow with whatever they have. These actions are driven by a genuine desire to contribute and help and hopefully, it will help them succeed.

How can our readers continue to follow you or your company online?

They can reach us through LinkedIn or our website ( and leave their questions in the contact form.

Thank you so much for sharing all of these insights. We wish you continued success and good health!

About the Interviewer: Chad Silverstein is an accomplished entrepreneur and visionary leader. He started his first company, Choice Recovery, Inc., while attending Ohio State University and grew it to become an industry outlier before selling the business after 25 successful years. With the launch of his second venture, [re]start, a career development platform, Chad aimed to help people find meaningful career opportunities. Under his leadership, his team was recognized as a “Top Workplace” award winner for over a decade, twice being ranked the #1 small and medium-sized business to work for in Central Ohio. Chad sold [re]start in 2023, enabling him to focus on building an online community of high-performing leaders and continuing to make a positive impact in people’s lives.