Drew Jessup
Brand Manager
Consumer Marketing, Digital & Retail
I’ve spent 14+ years building, repositioning and growing consumer-facing and service brands. My experience connects consumer insight, brand strategy, integrated campaigns, digital and social marketing, retail experience and commercial performance, from both the advisor and owner sides.
200+
Brands and businesses supported
14+
Years building brands
Brand management from insight through execution
My experience spans owner-side brand leadership, agency strategy and hands-on marketing execution. I translate customer and commercial insight into positioning, campaigns, digital experiences, retail environments and offers—and stay involved through creative development, implementation and performance review.
I help founders and leadership teams make commercial decisions that shape what comes next.
Selected Work
2017-PRESENT • PETERBOROUGH, ONTARIO
House Fitness
Brand Management / Consumer Marketing / Digital & Social / Customer Experience
Role: Brand Manager & Owner
CHALLENGE
Reposition and modernize a struggling independent gym while improving the member experience and restoring sustainable commercial performance.
The business had a loyal core but no clear position in a market crowded with discount chains and boutique studios. Pricing was inconsistent, the offer was hard to explain, and the physical space did not reflect the quality of the coaching happening inside it.
WHAT I LED
Brand positioning and identity
Membership and pricing strategy
Website and digital experience
Social and promotional campaigns
Member acquisition and communications
Physical environment and customer experience
Revenue and operational performance
EXECUTION
I started with the commercial objective and worked back to the brand. The repositioning gave the gym a single, defensible idea; serious coaching in a place that treats you like a person, and every decision after that had to serve it.
The membership offer was rebuilt around clearer tiers and pricing that reflected the value of coaching rather than floor access. New services extended the offer without diluting it. Identity, website, member communications and the physical environment were redesigned together so the experience matched the promise from the first ad to the first session.
Acquisition ran as a continuous program rather than one-off promotions: campaign concepts, messaging and creative direction developed in-house, then executed across social, paid and email against a monthly member-growth target. Behind it, stronger operating systems made the results repeatable.
RESULTS
38%
Increase in annual revenue over two years, through pricing strategy, membership redesign, new services and stronger operating systems
2 years
Recognized as Best Gym in Peterborough two years running.
2025-2026
Durham College
Integrated Campaign / Digital Marketing / Paid Media
Role: Campaign lead and digital strategist
CHALLENGE
Reach adult learners considering a return to education, and convert interest into enrolment; an audience that researches quietly, compares options across search and social, and drops out of the funnel when the next step is unclear.
WHAT I LED
Audience strategy and campaign positioning
Messaging and content development
Paid media planning across search and social
Conversion-focused landing pages
Performance review and optimization
EXECUTION
The campaign runs as one connected system rather than a set of channels. Audience strategy set the priority segments and the objection each one needed answered; messaging and content were written to those objections; paid media in search and social carried them; and purpose-built landing pages removed every step between interest and application.
Campaign performance data feeds directly back into execution — creative, targeting and page copy are refined against what the funnel actually shows rather than at fixed review points.
RESULTS
Achieved full course enrolment by the end of Year 1
2024 • LINDSAY & BOBCAYGEON
Kindred Coffee Bar
Brand Identity / Retail Experience / Environmental Design
Role: Brand and retail experience lead
CHALLENGE
Launch a community-focused coffee bar with an identity strong enough to travel between two small-town locations without losing the feeling of a local.
WHAT I LED
Brand identity and positioning
Retail strategy and space planning
Materials, signage and environmental design
Customer-facing details across both locations
EXECUTION
Space planning established the sightlines and pace of service; materials and signage carried the identity; and customer-facing details, from the counter to the menu, were designed to feel consistent across both locations.
RESULTS
Two locations opened in Lindsay and Bobcaygeon with one coherent retail experience
2020-2022 • TORONTO
King x Portland
D2C Brand / E-Commerce / Offer Design / Product
Role: Co-founder, brand, product and e-commerce
CHALLENGE
Build a direct-to-consumer subscription brand in a crowded menswear category, where the product is easy to copy and the offer has to do the differentiating.
WHAT I LED
Brand development and product curation
Packaging and unboxing experience
Offer and subscription design
E-commerce and customer experience
EXECUTION
Curation, packaging and the subscription offer were designed as one product. The box had to arrive feeling considered, and the offer had to make the next delivery easy to justify. The brand was later repositioned around seasonal style and convenience, which simplified both the buying decision and the merchandising calendar.
RESULTS
Co-founded, scaled and sold the business
A full cycle from launch to exit
Focus Areas
Capabilities
Consumer Insight & Positioning
Integrated Campaigns
Digital & Social Marketing
Retail & Customer Experience
Brand Systems & Creative Direction
Performance & Commercial Growth
I help teams make commercial decisions and roadmaps that define the next chapter of their business.
How I Lead Brand Growth
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.
UNDERSTAND
Consumer, category, competitive and commercial context.
DEFINE
Positioning, proposition, objectives, KPIs and creative brief.
ACTIVATE
Social, digital, web, retail, packaging and environmental execution.
OPTIMIZE
Review performance, customer response and frontline learning; refine accordingly.
Owner-side accountability. Agency breadth. Hands-on execution.
I bring the strategic perspective to identify the opportunity, the creative judgment to shape the work and the operational experience to get it into market.