The Challenger Brand Agency
Contact Us


Life is too short to work with people you don’t like and on things you don’t care about.
Asset 8

5&Vine helps Challenger Brands win. As a certified B Corporation, we partner with businesses to help them drive social impact and real profitability.

We’ve collaborated with some of the world’s largest VC’s to accelerate growth for Challengers in their portfolio. We’ve helped them raise over $1.4Bn in follow-on financing, guided three brands to acquisition and supported two as they went public.

Our success in developing go-to-market strategies, value propositions, growth strategies, and new products is celebrated in Fast Company, Rolling Stone, Forbes, The Globe and Mail, Entrepreneur, BetaKit, and Bloomberg, among others.

Look, we get it. We know you’ve looked at those other agencies and brands and felt something missing. We felt it too. That itch for meaning, for purpose in something greater.

That’s why we work with brands that are making a real difference. These brands play in the world of clean energy, organic food, circular fashion, financial literacy, and so much more.

These are 5&Vine clients.

Life at 5&Vine

We believe you’re the average of the 5 people you spend the most time with. That’s why we choose to engage with people that reflect the morals, drive, and compassion we value.

You’ll be learning from a team that genuinely cares, you’ll make significant contributions from day one, and you’ll have ample opportunity for mentorship and advancement. And most importantly, you’ll enable businesses that aim to better our world.

Positive Team Culture
Positive Team Culture: You’ll be joining a team that has the hunger and talent to win, heart and integrity to do right by their team and clients, and the optimism and tenacity to realize traditional and nontraditional approaches.
Mentorship: You’ll access valuable constructive feedback to improve your leadership, client-management, and technical skills, and will have the opportunity to be a mentor within our core and client teams.
Meaningful Impact
Meaningful Impact: You’ll be responsible for accelerating the momentum of high-growth B2C and B2B brands that are challenging the status quo to drive outcomes that benefit people and the planet.
Career Growth
Career Growth: You’ll be exposed to a number of game changing companies from across the globe, the executive teams that drive them, and the VCs that back them – earning valuable skills to accelerate your career.
Flexible Remote Work
Flexible Remote Work: Set up your remote office from anywhere +/- 3 hours from the EST time zone, and enjoy location and time freedom.
Competitive Salary
Competitive Salary: For the impact you’ll have, you’ll be rewarded. We offer a competitive salary and bonus for all team members.
Health Benefits
Health Benefits: We provide vacation time off to disconnect, and Group Plan Coverage as well as a flexible Health Spending Account for you to personalize the benefits that matter most.
Parental Leave
Parental Leave: We believe in equal treatment for all families welcoming a child into their lives. We offer a competitive leave top-up plan, benefits, baby bonuses and flexible work schedules to return to work smoothly.
  1. We THRIVE ON BEING REAL. We win while transacting in truth and authenticity. We achieve success while bravely acting with honesty, transparency, and genuine intent.
  2. We go AGAINST THE GRAIN. We’re not afraid to challenge the status quo to make the world better. We speak out against wrongs and use discomfort to propel us – and our clients – to take action and achieve the ‘never-been-done-before’.
  3. We create scenarios where EVERYBODY WINS. We don’t follow the old ‘winner takes all’ model where winning comes at the expense of others. We work towards solutions where workers, customers, the environment, and profits are valued at the same time.

Don’t See Your Dream Role?

We’re always in hiring mode – in search of people with the intellectual horsepower, depth of humanity, and drive to help our clients win. So if you don’t see a role that fits, don’t let that stop you from reaching out and helping us understand how we can win together. Reach out to [email protected].


We aim to respond to everyone within 2 weeks. We’ll let you know if we’d like to speak with you, need more information, or if your application isn’t a fit for what we’re looking for at the time.

No, but it would certainly be helpful. We’ve found that individuals often embrace a Challenger mindset both inside and outside of work by questioning norms and devising creative and powerful solutions that benefit business and society.

If this sounds like you, amazing. Regardless, we’d encourage you to spend some time learning about Challenger Brands if you’re interested in a role with us.

Co-Founder Mentality – We hope that everyone on the team brings a co-founder mentality to the role, and identifies opportunities for us to be better and then works to make that a reality. No work should be below you. We are a team and everyone gets their hands dirty regardless of their seniority.

Intellectual Horsepower – We partner with organizations to help them solve complex problems with incomplete information. Smart and capable problem solvers do well.

Collaborative – We are a cross functional team of really nice and capable people. We don’t have capacity for drama or bullshit. We want to enjoy each other’s company, celebrate our successes, learn from our mistakes, and work together to achieve outcomes that are better than our individual contributions.

Humility and Humour – You’ll be joining an exceptionally capable team, which means you’re likely exceptionally capable too. Now that we’re clear on that, let’s make sure to use that as fuel to do better and be better. And also be cool, and be silly. Life’s too short to take everything so seriously.

Integrity and Morality – Act honorably. Treat the clients budgets as if they were your own, and their business as if they were shared dreams and passions. Do right by our clients, our team and the world. If something doesn’t seem right, say something and let’s find a way to resolve it.

Organized – The team and client is depending on you. You will have a heavy influence on the timelines and scope of work, but once we commit, we need to deliver. Things will go wrong along the way, and we’ll be there to support you, but it is certainly helpful if you’re able to flag some of those risks and put in place contingency plans.

Skilled Communicator – Whether you’re sending a Slack message to a member of the team or presenting to a client, we need skilled communicators and storytellers that can succinctly and clearly convey their point.

They have likely underperformed in at least one of the areas noted above in ‘What are the common traits of candidates that are a good fit?’. The other areas that we’ve observed are:

Variety. You’ll likely be working with multiple clients at the same time, but they are unlikely to be the same size projects (some big and some small). Some of these may be in Europe, the United States or Canada. And across a variety of industries ranging from organic food, fintech, medtech, education, renewable energy and fashion, with wildly different deliverables to fit their unique scopes of work. If that kind of variety gives you energy, this is the place for you. If not, you may not be happy here.

Extra. Rarely do we have the perfect team size. Sometimes we have too many people for not enough work, other times we have too much work for not enough people. To manage these ups and downs, we help each other out, support non-profits with pro-bono work, engage freelancers, and ultimately grow our team. But that doesn’t mean there aren’t moments of craziness in between that push us to be better. Individuals that find workload variability stressful, may not be happy here.

The interview process is both demanding and exciting, similar to the work we do as Challengers! Depending on the position, it may involve a series of interviews beginning with a video interview that you can complete on your own time, a phone call or video chat with one of our team members, completing a case study or project related to your discipline, time to answer your questions, and hanging out with us to ensure there is chemistry.

No. We keep meetings to a minimum. We have one team meeting a week, a one-on-one with your manager, and then every two weeks we do a social. That’s it. Everything else is ad hoc and based on the clients you’re engaged with.

We used to have an office with a beautiful view of the CN Tower and Toronto skyline, but we gave that up at the beginning of quarantine. And now we’ve embraced being virtual with team members across the country and a flexible Work From Anywhere policy so long as the time zone is +/- 3hrs from Toronto so that a core part of our day can overlap.

Please be aware that 5&Vine never conducts hiring through platforms like WhatsApp, Telegram, or Instagram DMs, nor do we pay for social media engagement.

Should you receive any suspicious communications claiming to be from us, please report the sender immediately. 

To learn more about identifying scam accounts, see this article from the FTC.

Continue Message