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5 Interesting Learnings from Expensify at $140,000,000 in ARR

SaaStr

Expensify: Founded in 2008 … 13 years ago. 119% NRR from SMBs!! Still, 119% NRR from SMB is world-class even for 5+ seats accounts and sometime to strive for if you have similar sized customers. #4. An SMB sale, but less and less a single seat sale. A long, tenacious path to $100m ARR, and then … Boom!! *

Scale 328
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The SaaS Org Chart Live with David Sacks (Podcast #491 and Video)

SaaStr

In 2008, he founded Yammer, an enterprise software company that David grew to 500 employees and $60 million in sales. Positions Needed: Enterprise AEs, Mid-Market & SMB AEs, SDRs, Sales Ops, Sales Engineer. Positions Needed: Enterprise CSM, Mid-Market & SMB CSM, Customer Support Reps, Implementation/Solutions Engineer.

CTO Hire 290
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5 Interesting Learnings from Paycom at $1.2 Billion in ARR

SaaStr

It was founded way back in 2008, and had a slowish start and a smallish IPO (as did most of us, back in the day). But founder-CEO Chad Richison has kept at it for 14 years, building it into an incredible engine, growing 31% at $1.2 Pretty normal for the “M” side of SMB, but fairly fast for the deal size. 40% EBDITA.

Scale 299
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How to Build a Product Customers Love and Drive Nearly $1B in Revenue Along the Way with Klaviyo CEO Andrew Bialecki

SaaStr

Finding Superfans Early On Jason starts by asking the meta-question: “You’re at $900M of ARR, growing 35%, 112% NRR from SMBs, and 14% free cash flow. They supply their customers with a full marketing suite and customer data software for thousands of SMB, e-commerce businesses. Is there a downturn?” For Klaviyo, the answer is no.

Revenue 312
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Sales and GTM in Uncertain Times with Adnan Chaudhry and Matt Garratt (Video + Transcript)

SaaStr

And he also has the, I don’t know, benefit or dubious distinction, but lived through this before in 2008 and 2009. Adnan Chaudhry: One of the guiding principles that helped me personally, I was here as Matt mentioned, I was here at Salesforce in 2008, 2009. It’s the SMB space. Adnan Chaudhry: Thanks, Matt.

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Software-led payments: What’s on the horizon for platforms in 2025? | Episode 46

Payrix

That could be brand, that could be how the SMB interacts with the consumer. I think if you’re looking down at your shoes, this could catch you here in the next couple years and look back 2008, we had a huge downturn, tons of winners were made out of that. And some might say, quote, unquote, controlling the experience.

Payments 130
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8 Tough Lessons from Closing 12,000 Customers at WebPT (Video + Transcript)

SaaStr

From that point on, we built a product and we launched it in February of 2008 out of a back of a coffee shop with one employee. So I went down the hall, met with the head of marketing, and I discovered a lot about in bound SaaS, about SMB, the importance of building this machine as I call it now that generates all these lovely leads.

Scale 187