IF YOU'RE HERE, YOU'RE MOST LIKELY A FOUNDER, A PROGRESSIVE CEO OR ENTREPRENEUR READY TO INVEST IN SOME IMPORTANT WORK TO GROW THE COMPANY YOU SO DEEPLY LOVE.
At Ruby + Foster my goal is to help you find clarity and focus, through brand + business strategy.
I'm a strategic business advisor for entrepreneurs + CEOs like you, operating as a fractional CMO, guiding your marketing efforts. I work with your in-house teams and bring in best-in-class creative resources as needed to solve your biggest marketing challenges.
ANNA
HALFPENNY
FOUNDER / CMO
Here's my deal:
I’m a brand and business builder with over 20 years of experience leading marketing and advertising efforts for both global and national brands. My background spans marketing & brand strategy, business development, content creation, marketing fiscal planning, communications strategy and operations,basically, all the pieces that help a brand grow and thrive.
In 2018, I launched Ruby + Foster, where I work as a Fractional CMO, partnering with founders and CEOs to shape and drive their marketing strategies. In 2022, I expanded the business to better support small businesses with services tailored to their goals - bringing BIG brand thinking to their small businesses. I’ve also built three of my own brands from the ground up, so I know firsthand what it takes to start, scale, and sustain.
I’m big on supporting entrepreneurs, whether that’s mentoring through The Forum and the Chai Tech Accelerator program, partnering with Meridian Credit Union to develop and launch their Good Business online Learning series, or running my own brand and business academy.
I also love staying connected to the arts and proudly served as the marketing chair on the board of Orchestra Toronto and was their marketing advisor for over 3 years.
GETTING PERSONAL
Born into entrepreneurship, I grew up in my family’s pizzeria, taking orders, prepping ingredients, and even designing flyers by age 11.
Did you know? I've built and sold two businesses: a CrossFit gym and an organic juice bar, giving me hands-on insight into the real-life journey of small business owners.
I genuinely love creating content. My socials are filled with actionable marketing tips and tricks, all shared to help business owners grow with confidence.
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Make sure to follow me there.
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LinkedIn: Anna Halfpenny
IG: @rubyandfoster
TikTok @yourmarketingmentoranna
Solo entrepreneurs have my heart. I’ve been in their shoes, and I admire their grit, resilience, and creativity. Supporting them is one of my biggest passions.
I’ve worked behind the scenes with some of the most iconic brands in the world, helping craft globally recognized campaigns. Now, I channel all that experience into elevating my clients’ brands.
​When I’m not strategizing for clients or creating content, I’m spending time with my family, watching my daughter shine on stage as a competitive dancer, cheering on my son as he trains hard on the soccer pitch to become the next Messi, or soaking up the summer sun in Greece. You’ll find me sipping coffee, chasing sunsets, or dreaming up my next big idea.
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THE COMPANY I KEEP
