From Monolith to MACH: How Tovi Heilbronn transformed ecommerce at Harry Rosen
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Get the full episode here
TL;DR - What you'll learn:
- Why MACH architecture transformed Harry Rosen’s ecommerce experience
- How COVID opened a rare window for digital reinvention
- What it takes to modernize legacy systems without accruing new tech debt
- How the Herringbone app created a new kind of personalized, digital clienteling
- How to pitch and budget transformation projects that impact the bottom line
- Why upstream alignment between business and tech makes or breaks replatforms
- What Tovi’s new consultancy, Uncork Solutions, is focused on—and why now
“Digital transformation fails when tech leads, and business follows. They have to be true partners—or the whole thing breaks.”
— Tovi Heilbronn, Principal Consultant at Uncork Solutions
Inside Harry Rosen's transformation
Tovi Heilbronn spent nearly a decade at Harry Rosen, evolving from developer to senior tech strategist. During COVID, he led a full replatforming of their ecommerce stack—from a brittle monolith to a MACH-powered, award-winning website.
- The old platform was “spaghetti code on spaghetti code” with low agility and high vendor lock-in
- Ecom was seen as a side channel—until stores shut down and digital became the lifeline
- Executive buy-in came when MACH architecture revealed a path to agility, speed, and integration
“COVID was a once-in-a-career opportunity. The world shut down, and we got the green light to build the future.”
— Tovi Heilbronn, Principal Consultant at Uncork Solutions
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Building the Herringbone app: Clienteling, reimagined
One of Tovi’s proudest projects? Herringbone—a digital tool for clothing advisors to curate outfits and build customer trust online.
- It digitized the “laydown” experience (curated outfits) usually done in-store
- Advisors could recommend items remotely based on cart history, preferences, and past purchases
- Built on the same MACH stack, it extended omnichannel personalization at scale
“MACH let us humanize ecommerce—and digitize the in-store experience.”
— Tovi Heilbronn, Principal Consultant at Uncork Solutions
Managing tech debt like a product
Modern stack ≠ clean stack. Tovi built a system of proactive governance to prevent the new MACH environment from becoming just another mess.
- “See Something, Say Something” developer contest to flag tech debt early
- 25% of dev effort budgeted for ongoing cleanup, tracked weekly at the exec level
- Every debt ticket was scored for severity, frequency, and business impact
“Tech debt isn’t optional maintenance—it’s critical infrastructure. Treat it that way.”
— Tovi Heilbronn, Principal Consultant at Uncork Solutions
What makes a successful replatform?
Tovi’s approach to ecommerce transformation isn’t just technical—it’s strategic.
- Business and tech must co-own the roadmap and the outcomes
- Align on value drivers before implementation begins—not during
- Don’t overpromise velocity without budgeting for refactoring and governance
“Composable tech doesn’t fix misalignment. If you don’t plan upstream, you’ll relive the same pain—just faster.”
— Tovi Heilbronn, Principal Consultant at Uncork Solutions
Why Tovi launched Uncork Solutions
Tovi’s new consultancy focuses on what most agencies skip: the high-leverage strategy work before build begins.
- Help brands plan composable transformations with clear ROI cases
- Design operating models that align stakeholders and prioritize value delivery
- Avoid common failure points: weak governance, misaligned incentives, and unscoped tech debt
“There's a playbook to this. You just have to know what questions to ask—and when.”
— Tovi Heilbronn, Principal Consultant at Uncork Solutions
Listen to the full episode now
Learn how Tovi Heilbronn reimagined ecommerce at Harry Rosen—and what he’s helping brands solve today.
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