The Zebra: Scaling an Insurance Comparison Platform

At ITC Vegas 2025, Katie Gold, vice president of insurance sales at The Zebra, describes how she built a career across sales, insurance and now InsurTech. Gold began in car sales during college, then moved into insurance claims when she needed a more family-friendly path. That claims experience showed her what customers are really paying for and how policies work at the moment of loss.

When the pandemic hit, Gold lost that role while her sister in Austin pointed her to The Zebra, which was listed as a top 50 place to work. Gold applied, joined in 2020 and moved back to Texas and since then, she’s moved through frontline, service manager, sales director and senior director roles into her current position heading insurance sales.

Gold explains that The Zebra is an insurance comparison platform, similar to Kayak as consumers enter basic details and can instantly compare multiple insurance carriers in one place instead of going site to site. They can then either click through to buy directly from a carrier or be routed into The Zebra’s agency, where licensed advisors help over phone or chat. While ad revenue matters, Gold is clear that the strategic focus is on selling and binding more policies, improving retention and building recurring revenue rather than one-off clicks.

On the service side, Gold points out that voice calls make it easier to build rapport and understand what customers need. Digital channels like chat are trickier, so her team trains advisors to keep things human: asking the right questions, sharing useful context and offering quick “nuggets” that guide people rather than just pushing links.

AI comes in as a support tool, not a substitute for advisors and Gold talks about pairing “tech and talent” to make quoting smoother, give managers better insight and automate routine work like payments, policy document uploads, FAQs and policy audits. That lets humans focus on moments where people want reassurance and explanation, such as buying a home, handling complex coverage or adding a new driver.

Gold contrasts this with her earlier experience in traditional insurance, where change was slow and weighed down by layers of structure. At The Zebra, the culture is fast-moving and experimental: the team is encouraged to test ideas, pull the plug quickly if they don’t work and “fail forward” rather than stay stuck. Crucially, she notes that they’re preparing for a large new hiring class of licensed advisors.