From Local Guitar Store to $1B+ E-commerce Leadership
Driving growth starts with understanding people. For me, that began with teaching guitar lessons and eventually translated into helping large companies scale online.
Strength without noise. Clarity over complexity.
Long-term growth under pressure.
The name Oakleaf Digital comes from my surname, Ekblad -- "oak leaf." It reflects my Finnish-Scandinavian heritage and the values behind my work.
When I'm not working, I'm usually in the studio—playing guitar, drums, bass, or keys, and running live sound. At home, I've been married for 20 years, have two kids, and share the house with two dogs (Pancake and Biscuit) and a bunny named Whiskey Moon.
My wife dreams of a place where the animals can run free. Everything I do professionally is driving toward building that ultimate farm experience, which we're calling "Colt Farm." Thanks for being part of the journey. :)
The Evolution of a Revenue Architect
Careers in retail strategy rarely start at the top; they start with the customer.
For a decade, teaching music lessons and working the retail sales floor at Kenny Z's Music provided foundational experience in how customers actually think, what they value, and how to guide them to the right purchase.
As e-commerce evolved, moving into B2B sales and manufacturer representation at companies like Austin Bazaar and Livid Instruments revealed the complexities of channel conflict. It highlighted the challenge of allocating co-op dollars and what it takes to negotiate major deals with national retailers.
At LiveIntent, stepping into the AdTech space meant mastering programmatic display, identity resolution, and how to monetize first-party data at scale. This provided the technical foundation required to understand how the modern web actually works.
The Sweetwater Era
These diverse experiences culminated during a nine-year tenure at Sweetwater Sound. Starting as the Director of Partner Marketing, bringing the manufacturer co-op program into the digital age drove 208% growth.
Moving into the roles of Senior Director of Performance Marketing and Vice President of Marketing and E-Commerce expanded the mandate to owning P&L outcomes for the largest online music retailer in the US ($1.8B+ revenue). This included managing $70M in ad spend across SEM, display, video, affiliate, and other performance channels.
The goal was never just to buy traffic; it was to build scalable revenue architecture. Aligning teams across engineering, merchandising, and marketing decoupled the tech stack, launched a Retail Media Network, reduced customer acquisition costs by 25%, and advanced AI and Generative Engine Optimization strategy.
Making Sense of It All
The way people buy has changed fast. AI is reshaping discovery, old systems are dragging performance, and teams are often working in silos. You don't need more theory. You need someone to design the right systems, set them up with your team, and make sure they actually work. Whether you're a manufacturer trying to grow, a brand fixing your site, or a tech company proving value, I connect technical decisions to business results.
Explore ServicesFAQ
What's your background before consulting?
Jeff Ekblad worked from the sales floor (Kenny Z's Music, Austin Bazaar, Livid Instruments) through B2B and AdTech (LiveIntent), then spent nine years at Sweetwater Sound as Director of Partner Marketing, Senior Director of Performance Marketing, and VP of Marketing and E-Commerce.
What did you do at Sweetwater?
Jeff drove digital strategy for the largest online music retailer in the US ($1.8B+ revenue), aligned engineering, merchandising, and marketing, launched a Retail Media Network, reduced customer acquisition costs by 25%, and advanced AI and GEO strategy.
Why start Oakleaf Digital now?
Retail is shifting again: AI is changing product discovery, legacy tech stacks aren't tying to revenue, and execution stalls in silos. Companies need blueprints and orchestration, not just advice—whether they're manufacturers, D2C brands, or MarTech providers.
Who do you work with?
Manufacturers, D2C and omnichannel retailers, and MarTech or AdTech providers that need someone who has operated at scale and can translate strategy into executable systems.
What's the best way to get in touch?
Book a strategy call or use the contact form below. The first conversation clarifies your priorities and whether a fractional engagement or sprint is the right fit.