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Welcome to another episode of Category Visionaries — the show that explores GTM stories from tech’s most innovative B2B founders. In today’s episode, we’re speaking with Ori Entis, CEO and co-founder of Staircase AI, a customer intelligence and analytics platform that has raised $5 million in funding.

  • Ori’s background growing up in Israel, serving in the military, transitioning from engineering to the startup world, and the inspiration behind founding Staircase AI.
  • How Staircase AI uses AI to analyze millions of customer interactions across channels, forecast churn risk, reveal growth opportunities, and empower customer-facing teams.
  • The challenges of driving early adoption, landing first customers, and navigating the hype and skepticism around AI in the B2B SaaS space.
  • Staircase AI’s pivot from a product-led growth (PLG) model to an enterprise sales approach, and the lessons learned from failing fast and adapting to market realities.
  • The evolving role of customer success leaders in SaaS and the importance of leveraging AI-powered insights to navigate retention, expansion, and relationship-building.
  • Ori’s vision for the future of artificial customer intelligence as a sentient, augmentative platform that enhances human efficiency without replacing jobs.


Embrace the "Fail Fast" Mentality:

Staircase AI's journey highlights the importance of being willing to pivot when things aren't working. Despite the allure of product-led growth, Ori and his team recognized early on that PLG wasn't the right fit for their product and target persona. By failing fast and course-correcting to an enterprise sales model, they were able to regain traction. Founders should cultivate a culture that celebrates learning from failure and adapt quickly when data reveals a need for change.

Balance Conviction with Data-Driven Decisions:

As a startup founder, it's easy to fall in love with your own ideas and resist pivoting based on data. Ori shares how he had to temper his impatience to change messaging and trust his team's data-driven approach to iterative testing. While conviction is essential, founders must also be humble enough to let data guide critical decisions around positioning, features, and GTM. Striking this balance accelerates the path to product-market fit.

Bring in Experienced Talent Early:

Looking back, Ori wishes he had brought in experienced leaders in areas like marketing and finance earlier in Staircase AI's journey. As a technical founder, it's tempting to try to cover all the bases yourself, but this can slow your growth. Founders should prioritize hiring seasoned operators who can shorten learning curves and help the company execute faster. Even if the talent market is tight, the right leadership hires pay major dividends.

Design for Organizational Adoption in B2B:

Staircase AI's PLG experiment revealed that bottoms-up adoption is challenging when a product requires broad data access and cross-functional collaboration. For B2B products that necessitate organization-wide buy-in, founders should design onboarding flows and value props with multiple stakeholders in mind. Solving for the needs of champions, influencers, and decision-makers across the org chart is key to driving successful implementations.

Stay Agile in Messaging and Positioning:

Ori estimates that Staircase AI's messaging changes every 3-6 months in response to product evolution, market maturity, and shifting customer needs. Rather than aiming for "perfect" positioning out of the gate, founders should prioritize testing and learning. By continuously collecting feedback and monitoring engagement data, startups can refine their narrative to resonate with ideal customers. Agility in messaging is a hallmark of category-creating companies.

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