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

SaaStr

By 2016, Procore was a multi-product, multi-stakeholder platform expanding into enterprise and mixed-use construction firms. We lost nearly every customer, Tooey admits. But the companies that survived the recessionmixed-use and commercial buildersbecame Procores new focus. That pivot paid off.

Scale 291
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5 Interesting Learnings from Datadog at $1.2 Billion in ARR

SaaStr

100k+ customers have gone from 50% of revenue in 2016 to almost 80% today: #2. You know this, but doing “all the integrations” can be a killer winning strategy. #7. From 2 $1m ARR customers in 2016 to 145 today. $100k+ customers are key to ARR growth. More product, more products, more products. 450+ integrations.

Scale 362
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The Great AI Reset: It’s Time to Refound Your Start-Up. Now.

SaaStr

New pitch decks without an AI strategy aren’t even making it past associates. [link] — Akshay Krishnaswamy (@hyperindexed) May 5, 2025 The Pre-AI Stigma Is Real If you founded your SaaS company before 2023, you’re wearing the “pre-AI” label whether you like it or not. The market has fundamentally shifted.

AI Search 186
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The Best SaaS Articles of 2016 From Around the Web

Hitenism

2016 has been a year where knowledge has become freely available for anyone interested in knowing about all things SaaS. This slide deck comes from Brian’s brilliant SaaSFest 2016 presentation. Good customer support is the most underrated sales strategy. Thomas Smale , How to Value a SaaS Business in 2016.

Scale 152
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A Tale of Two Go To Market Strategies

Tom Tunguz

After last week’s post, Is There a No Man’s Land in SaaS ACVs , a founder asked me to highlight some of the go to market strategies in different segments. Based in Massachussetts, the company generated $320M in revenue in 2016. and 14% in net income margin in 2015 and 2016. Contrast Fleetmatics with a Geotab.

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Samsara S-1: How 7 Key Benchmarks Stack Up

Tom Tunguz

Founded in 2016, Samsara has grown explosively from $119.9m The last public company to adopt a similar strategy also happened to be in telematics: Fleetmatics. Congratulations to the Samsara team on building an incredible company with a unique go-to-market strategy and achieving incredible scale so quickly. Enterprise Customers.

CTO Hire 362
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The importance of an effective product marketing strategy

Intercom, Inc.

Eventually they start selling it via word of mouth and little else before realizing that they need some sort of coherent marketing strategy if they want to accelerate growth. They believe that neither product nor marketing can excel in isolation, which has become a core principle of our go-to-market strategy today.