Fun with: Pets (Trupanion)
I never turned off my LinkedIn VP‑Ecomm alerts, so I’m running some as quick plays: surfacing the JD, breaking down the challenge, and showing how I’d approach it. Maybe: job seekers see roles and get ideas, others get a fun hot take, and companies get free consulting (wanted or not).
Today’s feature: VP, Ecommerce at Trupanion. The challenge? Scale pet insurance ecommerce into a disciplined, data‑driven growth engine.
Abby, our 13 year old Kelpidor: a handy way to say she was a rescue, we don’t know her genetics, maybe black lab and kelpie?
Release the hounds!
Looking at their financials (TRUP), here’s what stood out: over the last five years, the stock has fallen 36%, badly trailing pet‑sector and health‑insurance baskets, which are flattish to positive. The three‑year return is still rough (–30%), though the past year shows a modest +7%. A quick scan suggests they’ve leaned hard on cost‑cutting and enrollment. Investors are likely asking: is this the start of a turnaround, or just a bounce? The answer hinges on three levers — vet costs, margin discipline, and enrollment growth. Of those, growth is the lever Trupanion can most directly control, assuming cost‑cutting is largely tapped out.
This role is going to be all about fast and profitable growth.
Here’s a hot take on what I’d fix first:
Invisible in AI discovery. When I asked Copilot for the best pet insurance companies, it surfaced ASCPA, Pets Best, Prudent Pet, Lemonade, Embrace, Healthy Paws, and Fetch — but not Trupanion. That output leaned on sources like Forbes, NerdWallet, and U.S. News. If Trupanion isn’t showing up in AI, the fix isn’t simple. We’re just beginning to understand which sources matter, how to close content/product gaps, and how to influence brand visibility. We've been similarly jolted by the disruptive effects of mobile, social, programmatic media over the past 15 years. I've learned that it's more inspiring and effective to dig in and experiment vs play catch-up after others have figured it out.
Bloated journeys. Endless scroll and duplicative content dilute conversion. Streamlined paths — like a “help me choose” flow — would lift acquisition. At Microsoft, I ran global ops for the DTC store. Analytics told us our product pages — from Surface to Office — were overwhelming. Insurance can feel the same. Once we stripped content down to what users actually needed, conversions skyrocketed. We tested and rebuilt every journey, end to end, with that clarity.
Light on emotion. Insurance is sold on trust and empathy. Real pets and real stories would resonate far more than just plan info. With Surface, we learned the hard way that “speeds and feeds” didn’t win hearts — Macs did, because they felt personal. What moved the needle was connecting Surface with real stories of joy, underdogs (no pun), belonging. Stories, with specs, built demand.
Fixing gaps like these isn’t cosmetic — it’s growth strategy. Visibility in discovery, cleaner journeys, and deeper emotional resonance. And there’s probably a lot that we don’t see from the outside that will reveal itself: AdTech and MarTech capabilities, demand gen efficiency, first party audience data leverage, etc. I’ve found that when we start with the obvious, the rest reveals itself along the way. And the solutions all compound.
It takes prioritization, curiosity, iteration, and bias for action if you want to be best in show…
