Indicative

Jeremy Levy's journey to Indicative began not with analytics, but with dating apps. In 2006, he co-founded one of the first location-based dating companies built for mobile, tracking users in real time as they walked around. "When we started the dating company, I was single and married now, but it worked," Jeremy recalls. "I did meet my wife through the company." That early mobile venture became a laboratory for developing more sophisticated technologies. The team also built what became the first enterprise CRM, which they spun out in 2008 to a company called Xtify. When IBM acquired Xtify in 2013 (integrating it into their marketing cloud), Jeremy had proven he could identify market gaps and build enterprise software. Indicative itself was spun out from intellectual property developed during these earlier ventures—solving the problem of helping non-technical users understand behavioral data without needing to be data scientists.

Launched in 2014, Indicative differentiated itself in three key ways. First, it was completely data-source agnostic—unlike competitors like Google Analytics or Pendo, it didn't matter if data came from websites, apps, or data warehouses. Second, it provided unlimited analytical flexibility without templates or canned reports, designed so product managers and marketers could perform sophisticated analysis typically reserved for data engineers. Third, it broke from industry convention by not charging based on data volume. "We can see that writing on the wall with the way cloud services are moving and the price of storage is rapidly moving to zero," Jeremy explained. The company offered a billion user actions per month for free—a remarkably generous ceiling given that their customers were processing "many multiples of billions" of events monthly across their entire user base.

For years, Indicative operated as a traditional enterprise software company, supporting customers from Fortune 500 companies down to small startups. They structured pricing around a $999/month starter tier (roughly $12,000 annually), scaling up to several hundred thousand dollars per year for large enterprises. The team built an enterprise sales motion, with heavy-handed onboarding: Jeremy described going to customer offices for two hours twice a week to help teams build their first KPIs and dashboards. This hands-on approach paid off—they maintained less than 5% revenue churn once customers were properly activated. In mid-2018, about four years after launch, the company had raised over $4M across multiple rounds and employed 15 people in New York City, historically operating at or around breakeven.

In July 2018, Indicative made a strategic pivot by introducing a freemium model. The results surprised them: "We doubled our acquisition month over month" immediately after launch. However, this freemium shift revealed a critical challenge. While enterprise customers churned less than 5% annually once activated (because Jeremy's team had invested heavily in getting them to proficiency), the self-service model exposed a painful truth: customers signing up needed to manually build their own KPIs to see value. "We don't have a historical set of data for you. We don't provide you today any sort of out of the box metrics," Jeremy admitted. New users had to commit an hour or two building basic KPIs just to get initial value—a high friction point that should theoretically have driven higher churn than they were seeing.

From a monetization perspective, Jeremy also revealed that expansion revenue hadn't been a focus. Rather than pursuing seat-based or usage-based pricing (which his competitors relied on), Indicative upsold through feature modules: single sign-on, white labeling, custom domains, additional integrations, and data retention policies. This module-based approach meant they were entirely dependent on their sales team to expand accounts—a narrower growth lever than volume-based or seat-based models offered. Jeremy was willing to spend "almost 50% of first-year ACV" to acquire a new $1,000/month customer, expecting to recoup that investment within six months.

By late 2018, Indicative had "several hundred" total customers, "pushing about a thousand" when including free users. The company's focus had shifted entirely to the freemium growth lever. "We're really focused around growing this free tier," Jeremy stated, adding that tweaking paid tiers and revenue optimization were "not the primary focus right now." This represented a notable strategic choice: despite raising $4M and maintaining a lean 15-person team, Indicative was deliberately de-prioritizing near-term revenue expansion in favor of user growth and product-led expansion. Jeremy's parting advice to entrepreneurs—"fire faster, pivot faster, hire faster"—suggested the company would continue iterating rapidly on what worked.