Listen Here

| |

Conversation
Highlights

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.

Actionable
Takeaways

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.

Recommended Founder
Interviews

Chris Strahl

CEO of Knapsack

Chris Strahl, CEO of Knapsack: $7 Million Raised to Build the Future of Design Systems

Taylor Lint

CEO and Founder of Swantide

Taylor Lint, CEO and Founder of Swantide: $7 Million Raised to Revolutionize How Companies Design and Build Their GTM Infrastructure

Sam Fonoimoana

Founder & CEO of Datajoin

Sam Fonoimoana, Founder & CEO of Datajoin: $3.5 Million Raised to Help Brands Leverage Customer Behavioral Insights

Creating the Go to Market Category with ZoomInfo’s Bryan Law

CMO of ZoomInfo

Creating the Go to Market Category with ZoomInfo’s Bryan Law

Creating the Marketing Automation Category with Mark Organ

CEO of Eloqua

Creating the Marketing Automation Category with Mark Organ

Sam Mallikarjunan

Co-Founder & CEO of OneScreen

Sam Mallikarjunan, Co-Founder & CEO of OneScreen: $10 Million Raised to Power the Future of Offline Advertising

Parry Bedi

Co-Founder and CEO of Tingono

Parry Bedi, CEO of Tingono: $7 Million Raised to Help Companies Boost Net Revenue Retention

Jared Siegal

CEO and Founder of Aditude

Jared Siegal, CEO and Founder of Aditude: $15 Million Raised to Build the Future of Publisher Monetization

Tyler Strand

Co-Founder and CTO of Air

Tyler Strand, Co-Founder and CTO at Air: $38 Million raised to Build the Creative Operations Category

Marc Bernstein

CEO and Founder of Balto

Marc Bernstein, CEO and Founder of Balto: $52 Million Raised to Power the Future of Contact Centers

Adrien Menard

CEO and Co-Founder of Botify

Adrien Menard, CEO and Co-Founder of Botify: $82 Million Raised to Build the Future of SEO

Tine Karlsen

Co-Founder & CEO of Vev

Tine Karlsen, CEO and Co-Founder of Vev: $7 Million Raised to Power the Future of No-Code Visual Design

Hikari Senju

CEO and Founder of Omneky

Hikari Senju, CEO and Founder of Omneky: $10 Million Raised to Empower Brands With AI-Powered Ads To Maximize Performance

Sangram Vajre

Co Founder and CEO of GTM Partners

Behind the Category: Creating the Account-Based Marketing (ABM) Category with Sangram Vajre

Jonathan Legge

Co-Founder and CEO of &Open

Jonathan Legge, Co-Founder and CEO at &Open: Over $35 Million Raised to Create the Future of Corporate Gifting

Patrick Woods

CEO and Co-Founder of Orbit

Patrick Woods, CEO and Co-Founder of Orbit: Over $22 Million Raised to Power the Future of Communities

Andy Mowat

CEO and Co-Founder of Gated

Andy Mowat, CEO and Co-Founder of Gated: Over $3 Million Raised to Build Noise Cancelling Headphones for Email

Leena Joshi

Co-founder and CEO of CloseFactor

Leena Joshi, CEO of CloseFactor: $15+ Million Raised to Automate Repetitive Sales Processes

Chris Golec

CEO and Co-Founder of Channel99

Chris Golec, CEO and Co-Founder of Channel99: $5 Million Raised to Power the Future of B2B Marketing

Tom Lee

Co-Founder of LOVO AI

Tom Lee, Co-Founder of LOVO AI: $7 Million Raised to Build the Future of AI Voiceovers

Ishveen Jolly

CEO and Co-Founder of OpenSponsorship

Ishveen Jolly, CEO and Co-Founder of OpenSponsorship: Over $5 Million Raised to Build the Future of Sports Influencer Marketing

Pierce Ujjainwalla

CEO of Knak

Pierce Ujjainwalla, CEO of Knak: $25 Million Raised to Empower Enterprise Marketers with Codeless Email and Landing Page Creation

Creating the Sending Management Category with Sendoso’s Kris Rudeegraap

CEO and Co-Founder of Sendoso

Creating the Sending Management Category with Sendoso’s Kris Rudeegraap

Daniel Erickson

Founder and CEO of Viable

Daniel Erickson, CEO of Viable: $9 Million Raised to Build the Future of Customer Feedback Analysis

Thomas Millay

CEO of DemandJump

Thomas Millay, CEO at DemandJump: Over $25 Million Raised to Power the Future of Content Strategy

Ashish Nagar

Founder & CEO of Level AI

Ashish Nagar, CEO of Level AI: $35 Million Raised to Power Contact Centers of the Future

Michael Bamberger

CEO and Founder of Tetra Insights

Michael Bamberger, CEO and Founder of Tetra Insights: $7 Million Raised to Power the Future of Qualitative Research

Jonas Rinde

CEO of Nomono

Jonas Rinde, CEO of Nomono: $15 million Raised to Power the Future of Podcasting