SaaStr 786: Going Long: How Procore’s Founder Tooey Courtemanche Built a Billon-Dollar SaaS Empire Over 23 Years

What does it take to build and scale a vertical SaaS giant over two decades? According to Tooey Courtemanche, CEO and Founder of Procore, it’s about focus, perseverance, and a relentless commitment to customer success.

In a recent conversation with SaaStr CEO and Founder Jason Lemkin, Tooey shared insights into his 23-year journey as CEO of Procore, the leading SaaS platform for construction management. From surviving economic downturns to scaling into a multi-product enterprise serving millions, Procore’s story is a masterclass in vertical SaaS excellence.

Tooey offers insights into maintaining work-life balance, strategic shifts during the financial crisis, transitions to multi-product offerings, and the impact of AI in the construction industry. Tooey also emphasizes the importance of customer-centricity and how Procore's brand has become ubiquitous in the U.S. construction market while exploring new international territories. Whether you're a SaaS enthusiast, a founder, or interested in the construction tech landscape, this episode is packed with valuable lessons and forward-thinking strategies.

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SaaStr hosts the largest SaaS community events on the planet.

Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier this year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.

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SaaStr 785: The Playbook for Going Upmarket with Stripe's CBO, Jeanne Dewitt Grosser, and Checkr's COO, Lindsey Scrase

Want to know when to move upmarket and how to actually pull it off? Jeanne Dewitt Grosser, Chief Business Officer at Stripe, and Lindsey Scrase, COO at Checkr, have done it multiple times at companies like Google Cloud, Stripe, and Checkr.

They came to SaaStr Annual to share what they’ve learned about making the move to go more enterprise actually work. They dive into their professional histories, strategies for startups when targeting and pivoting to enterprise markets, and the signals to watch for before making the leap. Learn from their experiences, including the importance of an aligned company push, the evolution of pricing, and tips for managing unit economics efficiently.

Don't miss their actionable advice on understanding unit economics and building a solid operating model to enhance your business success.

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SaaStr hosts the largest SaaS community events on the planet.

Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.

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SaaStr 784: From $1M to $3B ARR: Databricks CRO Ron Gabrisko on Scaling a Revenue Rocket Ship

In the latest episode of SaaStr's CRO Confidential Series, our host Sam Blond sits down with Ron Gabrisko, CRO of Databricks, to unpack the journey from $1M in ARR to crossing $3B ARR at the end of January 2025. With Databricks now one of the largest pre-IPO technology companies, with $10 billion of expected non-dilutive financing and a valuation of $62 billion, Ron's insights are gold for any revenue leader looking to scale.

Dive into the journey of Databricks, from its early days with less than a million in ARR to becoming one of the largest pre-IPO technology companies. Ron shares his insights on the importance of having a technical background in sales, strategic hiring, and the evolution of Databricks' pricing and customer acquisition strategies. Learn how leveraging unique business advantages and building strong community ties with customers can drive exponential growth. Whether you're a startup founder or a seasoned revenue leader, this episode is packed with valuable takeaways.

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SaaStr hosts the largest SaaS community events on the planet.

Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.

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SaaStr 783: How to Build a World-Class Customer Success Machine - Top Lessons from the CRO of Notion and VP of CS at GitHub

Join Erica Anderson, CRO of Notion and Abbas Haider Ali, VP of CS at GitHub, as they share their unique experiences and professional journey starting at GitHub and continuing to Notion.

Learn about building effective customer success teams, the importance of the right KPIs, balancing investments, and fostering great CRO-CCO relationships. Find out how both structured and pod organizational models can contribute to business growth, and gain insights into effective monetization strategies for various customer-facing roles.

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SaaStr hosts the largest SaaS community events on the planet.

Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.

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SaaStr 782: The Future of AI in B2B SaaS: Insights from Synthesia's CEO and Theory Ventures. Hosted by SaaStr CEO Jason Lemkin

As the AI revolution accelerates, it can be hard to keep up with the pace of innovation. SaaStr’s AI Day 2025 brought together the top minds in the SaaS, AI and Cloud to dive deep into the intersection of AI and B2B. Featuring insights from Victor Rippabelli, CEO of Synthesia, and Tomas Tunguz of Theory Ventures, Jason Lemkin leads the discussion that covered everything from enterprise AI adoption to the evolution of video technology and the changing landscape of venture funding.

Learn about the latest advancements in AI video models and how they enhance productivity and innovation. The discussion also explores the evolving landscape of venture funding in AI, the impact of cheaper AI models on enterprise costs, the dynamics of seat-based vs. outcome-based software pricing, and the future of AI agents in business workflows. Don't miss this insightful conversation on the current and future state of AI in the enterprise.

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SaaStr hosts the largest SaaS community events on the planet.

Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.

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SaaStr 781: The RevOps Playbook: Owner.com CRO’s Secrets to Scaling

Join Kyle Norton, CRO at Owner.com, as he dives into the fundamentals of operating a revenue team with excellence. In this 40-minute session, Kyle outlines his SaaS-focused 'revenue operating system,' inspired by analogies of the Iron Man suit. Learn about the four key components crucial for predictable revenue growth: measuring, managing, planning, and communicating. Kyle shares practical tools, metrics, and rhythms designed to streamline business operations, turning chaos into order and accelerating organizational growth. Gain insights from his extensive experience and take away actionable steps and templates to implement immediately in your own business.

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SaaStr hosts the largest SaaS community events on the planet.

Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.

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SaaStr 780: 9 Things You Can Do to Grow Faster this Year with SaaStr CEO and Founder Jason Lemkin

Join us for this insightful podcast where SaaStr CEO and Founder Jason Lemkin discusses the key strategies to differentiate a successful year from a mediocre one. Focusing on 9 practical and effective layers to add to your business, this session covers everything from outbound strategy, customer conferences, and going multi-product, to the importance of customer success and global expansion. Learn from real-world examples and actionable advice to drive your growth and add value effectively.

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SaaStr hosts the largest SaaS community events on the planet.

Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.

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SaaStr 789: What to Expect from a New CRO with Kathy Lord, CRO at Zensai and Jason Lemkin, SaaStr CEO and Founder

SaaStr CEO and Founder Jason Lemkin sat down with Kathy Lord, CRO of Zensai (and formerly of Intacct), to talk about what CEOs and CROs should really expect from one another, especially in those critical first 90 days.

Kathy shares her journey and insights, and together they discuss the critical aspects CEOs and founders should align on when hiring a CRO or VP of Sales, the importance of having a real 90-day plan, and the differences in expectations between a CRO and a VP of Sales. Kathy provides actionable takeaways for ensuring alignment and setting realistic goals while addressing common pitfalls in hiring executive sales roles. This episode is packed with valuable strategies and real-world examples, making it a must-listen for anyone involved in scaling up SaaS companies.

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SaaStr hosts the largest SaaS community events on the planet.

Hey everybody - thanks to the 10,000 of you who came out to SaaStr Annual. We had a blast and big news -- we'll be back in MAY of 2025. That's right, the SaaStr Annual will be a bit earlier next year, May 13-15 2025. We'll still be back in the same venue, in the SF bay area at the 40+ acre sprawling san mateo county events center. Grab your tickets at saastrannual.com with code JASON50 for an extra discount on our very best pricing.

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