Challenger Playbook
Canada's
Challenger Playbook
Canada is a Challenger Brand
There’s a quiet strength running through this country—a determination born from hardship, not hype.
Canada is more than a well-mannered middle power.
We are a country forged in extreme conditions—geographical, economic, and political.
We thrive in adversity, not just because we endure, but because we adapt, innovate, and lead.
And yet, when the world thinks of economic powerhouses—of dominant forces in business, trade, and innovation—they look elsewhere.
They shouldn't. Canada isn’t just keeping up with global shifts. We’re setting the pace. It’s time to tell that story.
What 5&Vine Leadership Delivers
Yes, we handle the essentials: funnel optimization, market prioritization, growth strategy, brand development, team hiring, and marketing org rebuilds. But we also go deeper, helping you craft investor decks, sharpen product positioning, introduce OKRs, and steer high-stakes decisions alongside the rest of your leadership team.
This is embedded leadership built to unlock your next stage of growth.
Brands we've worked with.
5&Vine possesses an exceptional ability to listen and collaborate, differentiating them from most agencies. They crafted a powerful brand positioning by flexing on the strength of our origin story, showcasing our commitment to sustainability and inclusivity, and deepening our connection to the consumer. I highly recommend.
What Drives Us
Our fractional approach, in practice
We help you see what others miss – then act on it. From competitive intel to marketing clarity, we’ll shape a strategy that fits your business and fuels your goals.
- Uncover blind spots and unlock unfair advantages
- Map strategy to capabilities, not just ambition
- Reframe your narrative and refine your go-to-market
- Align your team around what actually moves the needle
Why 5&Vine?
As your Fractional CMO and fully-integrated team, we lead from within—managing your budget, your priorities, and your people like they’re our own.
- Fill team gaps or become the team
- Recruit, hire, and onboard with long-term fit in mind
- Lead key decisions across leadership, product, and brand
Wondering if we’re a fit?
No marketing team yet
Growth acceleration
Mentorship or a second opinion
Interim leadership
Junior team, senior stakes
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What was most rare about 5&V is how quickly they understood the issues we were trying to solve. From our first conversation we started moving toward creative and bang-on appropriate solutions, and that kept going right through the end of the project. They were also super-responsive to any issues we had, which is the most important trait in a partner.
5&Vine was a crucial partner in developing a new name and brand for Rethink Climate. Name changes are always difficult – but 5&Vine never wavered in their commitment to develop a name and brand that would reflect our mission. We are delighted with the reaction we have received in the market, reflecting the high quality of their work. And they are just great people.
5&Vine understands challenger brands and helped us with a super meaningful rebrand that embodies our reason for being.
The team at 5&Vine has been amazing to work with. They are very knowledgeable and I truly believe they have the expertise to bring any business to the next level. They are great partners as they always try their best to stay flexible to our needs whenever we needed to pivot to a different direction. I would recommend them to any company who needs expert guidance and a team who would roll up their sleeves to get things done.
5&Vine was instrumental in transforming our brand into a Challenger with a strong sense of purpose. With a new name and brand, we are now standing out from established players, gaining recognition among our target audience, and accelerating customer growth. The impact has been incredible!
5&Vine led our brand repositioning and accelerated our growth. Their dedication, insights, and creative approach are evident in their process and impact. I would highly recommend them to any startup looking to take their brand to the next level.
5&Vine scaled our high-growth startup. They helped drive alternative pricing models, improved user engagement, evolved our creative, and drove revenue. They are great partners that adapted and grew alongside our business.
As a fellow certified B Corp, we were thrilled to work with the 5&Vine team that believes, as we do, business can be a force for good. 5&Vine helped us realign critical marketing efforts to reach new consumers seeking out sustainable, value-driven, and fashion-forward activewear.
5&Vine possesses an exceptional ability to listen and collaborate, differentiating them from most agencies. They crafted a powerful brand positioning by flexing on the strength of our origin story, showcasing our commitment to sustainability and inclusivity, and deepening our connection to the consumer. I highly recommend.
5&Vine are our trusted advisors and helped us build our Growth Marketing function. They provided actionable advice, tailored for our exact stage of growth. Even today, all of our marketing efforts rely on the strong foundation that we built jointly with their talented team.
5&Vine’s results can be expressed by a single word: stellar. Within weeks of launching our new brand, we have already started to see tangible business benefits. Thank you, 5&Vine, for the awesome work!”
5&Vine’s assistance was crucial in transitioning our focus to Borrowell’s Free Credit Score. They helped us mature our marketing function, and worked closely with our team to refine the metrics we track as well as our tactics and strategy.
5&Vine was critical to helping our company during a leadership transition. They engaged with our leadership and marketing teams to reset our strategy, putting us on a new course that continues to be successful. Would highly recommend!
As a fast-growing startup with a limited budget, we had to make every dollar count. We wanted an experienced CMO, specialists below them, and a marketing budget, but we couldn’t do it all – until we met the team at 5&Vine. 5&Vine jumped in at a critical time, quickly analyzed our issues and opportunities, and delivered.
5&Vine was my first hire when I took the helm of Mama Earth Organics, knowing they could help transform the business. They quickly began driving the performance we needed and developed a framework to build an enduring brand. 5&Vine are amazing business thought-partners, with a Swiss Army knife skill set that any-sized business will benefit from.
5&Vine was instrumental in helping to design and rapidly execute a robust marketing strategy that we’ve used to become the global leader in medical imaging. Results from their work were game-changing.
Acquiring customers is hard and any founder that thinks ‘it’ll happen on its own’ is fooling themselves. 5&Vine is the multiplier you need for your startup. They are game changers and our trusted partners.
5&Vine are strategy mavericks. They get to the core of your business and identify how to leverage marketing to drive growth. I would recommend their approach in a heartbeat.
5&Vine bridged a gap at a critical time. They were recommended to me by an investor, quickly built trust, and put our marketing team back on the rails. If I could change one thing, it’s that I should’ve hired 5&Vine sooner.
5&Vine was amazing to work with. We were looking for leadership and guidance on re-branding our company and that’s exactly what we got. Rahul is a true artist: from value proposition, to name, through to logo and design, we now feel like we have the foundation to build a transformational company in the employee well-being space. Thanks 5&Vine!
5&Vine is a partner that brings intellectual honesty, collaboration and a wealth of experience. It’s a partnership in an outcome-oriented mission. It’s an ally in the trenches when you’re getting your ass kicked. It’s a high five from a team you highly respect when you get something right.
The 5&Vine team have been an incredible resource for our brand. Love the quality of their ideas and our shared passion for creating a more just and sustainable world.
5&Vine launched our disruptive UK baby care brand into the US. The team was awesome to work with and packed a real punch in terms of quality of strategic thinking, creative approach and excellence in execution. There was instant rapport, partnership and trust. Their consumer insight helped us get a real understanding for the US market. Our US website has won awards and our paid channels have exceeded performance benchmarks. I would thoroughly recommend the 5&Vine team!
The team at 5&Vine are incredible partners. Their technical and design expertise, combined with their appetite for understanding the nuances of our business and industry, really set us up for success. We’re already seeing improved performance and our website better represents our brand. Big win, and a big thanks to 5&Vine.
5&Vine looked at our strategy through a new lens. They helped us expand into new revenue streams, new customer segments, and build in processes that were critical to scale.
5&Vine are amazing marketing strategists. They led marketing for Greenlight during our early days, and it was one of the best decisions we made.
We don’t consult. We co-pilot.
Challenger Brands FAQs
- Track record of success.Past success is a solid indicator of future success. Make sure they have a history of winning. Consider this in two regards. First, the depth of experience in your industry, be that sustainable brands, Fintech, D2C or B2B SAAS. Second, breadth of experience across industries, enabling them to bring best practices and innovative strategies to your challenger brand and sector, not just the standard textbook responses.
- ChemistryContext matters and contributes to success, be that an organization’s culture, the dynamics of the management team, or their stage of growth. Make sure you and your team have great chemistry with your Fractional CMO.
- Team and/or network.As your Fractional CMO understands your business and identifies barriers to growth, they’ll work to resolve them. This will often require a team. If you don’t have those individuals in place, you’ll need to hire them, and this can be very time consuming. And, even when they’re in place, the team will need time to build chemistry. Engaging a Fractional CMO that comes with their own team helps deliver results, fast.
- Strategy.Marketing doesn’t exist in a silo. It needs to work in collaboration with product, sales, customer support, finance and operations. A great Fractional CMO gets that, and is eager to be integrated into the team to both lend support and ensure that the solutions advanced are feasible.
Discover more in our blog: Q&A with 5&Vine Founder and Fractional CMO Rahul Raj
For Challenger Brands to successfully take on their industry’s leaders, navigate uncertain times and find a secure foothold, they need a marketing plan with backbone, designed by someone who truly understands strategic marketing and the Go To Market process. Typically, this is something left to a full-time CMO.
However, a Fractional CMO can be helpful no matter if you are a startup, mid-size, or enterprise company, as the experience that the Fractional CMO brings will be tailored to guiding teams through the specific challenges they face at their chapter of growth.
It’s not uncommon for a startup to lack effective marketing leadership. A Fractional CMO can mentor those in the marketing department and set up a vision that the team can follow into the future. As startups grow into mid-size and enterprise businesses, a Fractional CMO can bring fresh perspective to lead a rebrand, reach new audiences, and launch new revenue streams. Moreso, when existing marketing strategies are falling short, it can be a helpful sign that your company needs a Fractional CMO. A Fractional CMO can identify gaps and challenges in your new vision, and work with you to overcome them.
Discover more in our blog: When is it Time to Bring a Fractional CMO on Board?
Traditional CMOs work a standard 40-hour work week for one company, while Fractional CMOs work either a set number of hours each month or a few specific projects, typically for multiple companies at one time. Companies that hire a Fractional CMO are able to access marketing leadership and expertise at a fraction of the cost of a full-time, in-house hire, reducing risk.
Discover more in our blog: When is it Time to Bring a Fractional CMO on Board?
A Fractional CMO can be an incredibly helpful, low-risk investment for companies of all sizes, from startups to enterprises, that are in need of cost-effective marketing leadership who can drive results fast. With a Fractional CMO, a deadline is mapped and a strict timescale is outlined. By the time that deadline comes around, you’ll be secure in the knowledge that whatever you need reworking or building is done to the highest of standards.
At 5&Vine, our marketing planning process includes articulating your go-to-market, reframing your brand’s narrative and producing tailor-made strategies that promote growth and customer acquisition.
You can see examples of teams we’ve supported as their Fractional CMO by viewing our Case Studies.
A web design and development agency is a company that specialises in authoring, designing, and coding websites. Web design agencies typically have a team of SEO experts, copywriters, graphic designers, UI/UX designers, developers, and project managers who are responsible for creating and maintaining websites for clients.You can engage a Fractional CMO based on time or project. In the case of time, this typically ranges from ½ day a week to 3 days per week. To make best use of their expertise, you’ll need a team to execute. If you have an in-house team, part of their time will be in coaching and supporting that team to execute - including 1:on:1’s and team meetings. If you don’t have every capability needed (eg. you don’t have an in-house performance marketing team or graphic design) you can engage experts from your Fractional CMO’s team - ranging from ½ day to 3 days per week.
Additionally, you can engage a Fractional CMO to lead a project (e.g. new branding or a new website). The benefit of doing so is that the way that project is realized is through the strategic lens of a CMO. In the case of a website, it will be SEO optimized and conversion focused.
Learn more about our Services.
Financial experts and forecasters speculate that another recession is on the horizon. Whether this downturn will eclipse the Great Recession of 2008-2009 is yet to be determined, but there’s no denying the impact will be felt far and wide across the business world.
As one of the first to suffer from reduced budgets during downturns, the role of marketing will invariably shift over the coming months and years.
In 2025, the role of the CMO will evolve to require more agility than years prior, taking more pages from the startup playbook to squeeze value out of every last marketing dollar. This could be alternative pricing, acquisition models or reinvesting from paid acquisition to organic or referral.
A CMO in 2025 must be especially strong in:
- Data-driven decision making
- Customer experience and engagement
- Omni-channel marketing
- Application of emerging technologies into marketing strategies (i.e. AI, AR, VR, blockchain)
- Collaboration with IT and data teams
- Content strategy and storytelling
- Global marketing expansion
- ROI and attribution
Read more in our blog: The Role of Challenger Brand Marketing During an Economic Downturn
Bringing an outside perspective into your business can have a huge impact in effectively analyzing the challenges of your brand so you can figure out how to overcome them. Typically, the role of a Fractional CMO is to lead a company’s marketing strategy and investment so it can grow efficiently and with impact. Because Fractional CMO’s are quick hires that deliver value immediately, their skills are founded on speed, experience, and reducing risk.
Companies should hire a Fractional CMO when they are looking to bring marketing expertise and leadership within their team without the long-term cost of commitment. The Fractional CMO can mentor those in the marketing department and set up a vision that the team can follow into the future.
Discover more in our blog: When is it Time to Bring a Fractional CMO on Board?
Greenlight, a fintech Challenger helping parents raise financially-smart kids, is a definite standout. We helped position them to be the modern tool to reach that goal, developing a strategy that was as inspirational to young people as it was credible with parents, as well as position them for a Series A. By the end of our engagement, we had grown their customer base 3x, helped author their pitch deck and close a $20M series A led by Amazon, land an impressive range of Tier 1 press, launch an affiliate program, an advocacy and referral program, and built an in-house marketing team. Greenlight now has 5M daily active users and is valued at $2.3Bn.
Read more in the Greenlight case study.
Hiring a Fractional CMO can be a daunting task. Where can you find someone who understands the most effective way to grow your startup, is focused on delivering the KPIs your management team and board want to see, and will build your brand while doing right by your customers and team?
To help you find the right fit, we’ve outlined 7 questions you should be asking yourself when hiring a Fractional CMO:
- Do they have a proven track record?
- Are they data-driven in their decision making?
- Do you have a natural chemistry with them?
- Can they think two steps ahead?
- Can they communicate effectively?
- Are they in it for people and the planet?
- Does their expertise span the marketing mix?
Read more in our blog: Questions to Ask Yourself When Choosing a Fractional CMO
In 2023 we saw two opposing ideas converge in a very real way: technology and innovation VS authenticity and mindfulness. On the one hand, the world is thrilled about the advancements in AI and large language models, which are driving progress in healthcare (e.g. diagnostics and drug recovery) and finance (e.g. more precise trading decisions). On the other hand, Merriam-Webster Inc. selected “authentic” as its word of the year to highlight how the rise of AI and misinformation on platforms like Elon Musk’s X have made it more difficult to differentiate between what’s real and what’s fake.
To understand what's coming in 2025, we read the 78-page Edelman Trust Barometer survey of 30,000 people from the Challenger Brand POV so you don’t have to. See our summary here.
5&Vine is a full-service marketing agency that propels challenger brands that better the world. We offer:
- Marketing Strategy
- Branding & Naming
- Web Design & Development
- Digital Marketing
- Social Media, Influencers & Partnerships
Complete the Contact form and our CMO Rahul will be in touch within 3-5 business days for complimentary 30-minute consultation on your brand’s next chapter.
