Marketing Trust as a Product to Win Enterprise at Okta

This case study was created from an episode of the Product Marketing Adventures Podcast. It has been adapted into Dusted's case study format to preserve and showcase the guest's real-world experience. Written to preserve the voice of the true author, Kevin Gough.

Okta makes it easy to sign into workplace applications while keeping them secure and ensuring the right people have access. We were doing great in the mid-market, but moving upmarket meant landing larger, more complex Fortune 1000 and Global Enterprise accounts. These high-value, high-stakes deals had long sales cycles and multi-threaded buying committees. Microsoft was our main competitor—they had 20-year relationships, earned credibility, and people who had built careers on their stack. Trust is not a product per se, but our insight was that we needed to market the concept of trust just like we market a product, using the same tools and techniques, as a company-wide initiative spanning brand to sales.

Our deals were stalling because target enterprise customers weren’t willing to make the jump to a relatively new vendor. We had a superior product—side-by-side comparisons showed people preferred our capabilities—and the product was ready for the enterprise, yet win rates were not where we wanted them. Market research and sentiment analysis versus Microsoft, plus competitor claims around uptime and compliance, showed we weren’t at parity in perception even when our product could deliver. Vendor consolidation meant buyers wanted a few strategic long-term (ideally million-dollar) relationships; we needed market perception to match reality and gain the full buying committee’s trust so we could become one of their top-five vendors. The goal was to uplift conversions across the funnel, improve brand trust scores, and increase win rates against Microsoft in the enterprise category.

We treated trust like a product launch. Step one was mapping the broader enterprise buying committee (not just IT directors but VPs, CIOs, chief compliance officers, chief legal officers, and sophisticated procurement) and contextualizing trust for each stakeholder’s metrics: product teams cared about 99.99% uptime guarantees so traffic spikes wouldn’t lose signups; engineering cared about stable APIs that wouldn’t break integrations when versions changed. Step two was building a trust ecosystem of third-party and data-grounded proof points rather than just saying “trust us”—we advocated internally for stronger uptime guarantees (three nines instead of two), certifications, and transparency. Step three tied those proof points to customer business outcomes and engaged customers directly (e.g., JetBlue trusting us with a thousand flights a day). Step four was a long-game analyst strategy: listen and learn while planting seeds on our differentiators (thousands of integrations) so we could influence Magic Quadrant questions; we ultimately became a leader in the access management Magic Quadrant. Step five deputized the entire go-to-market org as trust ambassadors—sales got a trust playbook with compliance collateral, customer success got enablement for renewals and expansion, and we aligned metrics (brand perception, enterprise win rates, pipeline, renewals) so every team had skin in the game. It was a rolling-thunder, year-long initiative with quick wins alongside longer-lead items like engineering work and audits; cross-functional partners helped shape it early so launch felt shared rather than imposed.

We launched an updated trust.okta.com microsite as the transparency hub: a visual heat-map dashboard of historical uptime (green/yellow/red over six months), a full compliance section that put SOC 2, HIPAA, and FedRAMP documentation online instead of buried PDFs, and a launchpad for security research published by the security researchers and regional CISOs we were hiring. We created a sales trust playbook with specific compliance assets. In partnership with partner marketing we forged the “Velvet Alliance” with fellow Microsoft competitors (Box, Slack, Zoom) for best-of-breed brand association. We pushed internal stakeholders (engineering, legal, finance) for a stronger contractual uptime guarantee despite SLA credit risk, arguing the enterprise sales upside offset it. Analyst relations focused on getting our integration strength written into Magic Quadrant questionnaires. Website visuals shifted to rich purples and financial-services imagery signaling seriousness. Customer stories and the brand-perception study gave measurable before/after proof.

We ran a before-and-after brand study that showed increased brand trust/perception scores at the top of the funnel. Win rates rose specifically against Microsoft and other competitors in the enterprise segment. We saw an uplift in enterprise renewal rates (we weren’t losing deals back to Microsoft) and a lift in enterprise pipeline. The multi-threaded initiative delivered across the full buyer journey, and we became a leader in the access management Magic Quadrant. Everyone from sales to customer success acted as trust ambassadors, and the metrics that moved were the ones each team was already measured on.