Drew Jessup
Commercial Strategy
Creative Direction
I help leadership teams turn complex business challenges into clear decisions, stronger brands and measurable growth.
200+
Brands and businesses supported
14+
Years building brands and businesses
Growth opportunities rarely sit neatly within one department. They emerge between commercial strategy, brand, customer experience and operations. They become visible when those perspectives are connected.
I help founders and leadership teams identify the opportunities worth pursuing, make the decisions required to act and align execution around a clear commercial outcome. That might mean repositioning a business, reshaping an offer, improving pricing, expanding a customer relationship or translating strategy into a campaign, digital experience or new service.
At Sunday Roast, this approach helped generate 65% of new-revenue opportunities in one quarter and contributed 35% of agency revenue within a year through strategic expansion and client growth.
I help founders and leadership teams make commercial decisions that shape what comes next.
Turning Possibility into Growth
Selected Work
2017-PRESENT
House Fitness
BUSINESS REPOSITIONING/BRAND EXPERIENCE
Repositioned a struggling independent gym as House Fitness, aligning its brand, digital experience, physical environment and operating model around a clearer member promise. The transformation increased annual revenue by 38% over two years and helped earn Best Gym Peterborough in 2022 and 2023.
2024
Kindred Coffee Bar
BRAND IDENTITY/ENVIRONMENTAL DESIGN
Created a warm, community-minded coffee bar in Lindsay, developing the brand identity alongside the interior concept and physical build. The work translated the brand into a cohesive customer experience through space planning, materials, signage and thoughtful in-person details.
2025-2026
Durham College
INTEGRATED CAMPAIGN/DIGITAL MARKETING
Established and now leading the second year of an integrated enrolment campaign connecting audience strategy, messaging, content, paid media and conversion-focused landing pages. The program builds on first-year learning to reach adult learners more effectively across search, social and the college website.
2020
King x Portland
D2C BRAND/E-COMMERCE
Co-founded and later sold a Toronto-based direct-to-consumer sock subscription, building the brand across product curation, packaging, e-commerce and customer experience. Later led a brand realignment that sharpened its audience, evolved the identity and repositioned the subscription around seasonal style and convenience.
Focus Areas
Capabilities
Brand Strategy & Repositioning
Integrated Campaign Development
Social & Digital Marketing
Creative Direction & Design
Retail & Environmental Design
Product & Portfolio Strategy
Go-to-Market & Growth Leadership
I help teams make commercial decisions and roadmaps that define the next chapter of their business.
How Possibility Becomes Action
Possibility only matters when it's translated into something people can see, feel and act on. I connect strategic direction with creative execution so every touchpoint supports the same commercial objective.
I start with the commercial objective, consider the audience, then shape the idea across the mix of social, digital, web, retail, environmental and experiential touchpoints that serves it best.
DISCOVER
Understand the consumer, market and commercial objective. Find the behaviour, tension or opportunity the brand can credibly own.
DEFINE
Turn the opportunity into a focused proposition, message, experience and creative direction.
ACTIVATE
Bring the idea to life across the right mix of social, digital, web, retail, packaging, environmental and experiential touchpoints.
EVOLVE
Measure response, listen to customers and frontline teams, and refine the work to strengthen relevance and commercial impact.
Let’s Find
What’s Possible
Tell me what you’re building, where you want it to go and what’s getting in the way. Let’s see what’s possible.