Optimizing Delivery Routing at Scale

As a Group Product Manager at Wayfair, I lead three teams responsible for getting sofas, desks, and approximately 4.3 million types of home décor from Point A to “That corner near the window, please.” On paper, I run routing optimization. In reality, I manage the emotional rollercoaster between “I want this now” and “Why hasn’t it arrived yet?”

It started with a simple, slightly dangerous question:
What if we could promise faster delivery — without setting our operations (or margins) on fire?

So I did what any reasonable product leader would do. I built a fulfillment brain.

Not just an engine that connects trucks to warehouses, but a full-blown, context-aware, customer-sensing system that remembers what the customer saw on the product page, understands what they want at checkout, and commits to a delivery promise that won’t self-destruct in 24 hours.

One of the first things I tackled was delivery-date whiplash. You know, when a product says “Arrives Friday” on one page and “Maybe next Tuesday” two clicks later. I fixed that by adding memorycontext awareness — across the funnel. Now, delivery dates actually remember what they promised five seconds ago. Revolutionary.

Then came the Preference Manager — a system that gently stalks (let’s say “interprets”) customer behavior to learn their delivery vibe. Are you the “fast and furious” type or more of a “cheapest possible, I don’t care if it arrives next equinox” type? Either way, we tailor the experience to you.

At the core, I built two brains:

  • One deterministic, calm and stoic — great for stable, high-volume lanes.
  • One probabilistic, spicy and flexible — good at spotting chaos and saying, “Let’s try this instead.”

Together, they don’t just select the best route. They decide how to decide — based on real-time supplier hiccups, carrier tantrums, weather drama, or a truck that just straight-up forgot to show up.

Eventually, I scaled this logic to cover:

  • Returns (a polite way to undo mistakes),
  • Replacements (fixing what broke),
  • Multichannel fulfillment (because customers don’t care if it’s 3PL, supplier-direct, or warehouse elf magic),
  • And store shipments (yes, we ship from stores now — you’re welcome, planet).

The result?
A platform that reduced delivery time by 48 hours, boosted conversion by 12%, saved $80M, and cut customer service complaints like a well-placed refund.
Also, I no longer get nervous when someone says “routing.”

This wasn’t just optimization.
It was a reinvention of how trust, speed, and logistics dance together — and how a promise made at checkout can become a strategic advantage.

On a serious note, this system unified siloed logistics decisions into a platform governed by a profit-aware, customer-centric equation — one that balances speed, cost, and reliability using both deterministic rules and probabilistic intelligence. It redefined what fulfillment means: not a cost center, but a strategic differentiator.

I regularly share frameworks like this in my newsletter — it’s free, strategic, and built for leaders who want to turn logistics into leverage. “Network Strategy and Optimization

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