5 Interesting Learnings from SmartSheet at $1 Billion in ARR

So there’s a quiet leader in the work management space that’s quietly … blowing the doors off.

Everyone knows Atlassian, Asana, Notion, probably Monday.  But Smartsheet?

You should know them. They’re at $1 Billion in ARR now, growing an impressive 23%. The public markets aren’t completely in love with the space — it trades at an average $6.3 Billion, or just 6.3x ARR.  Asana similarly trades at just $4 Billion today on ~$700m in ARR, so about the same.

But Smartsheet is a good one. Undervalued?  Yeah, maybe so.

For the 8th year in a row, we’re expanding our Equality, Inclusion and Balance program.

We are proud that the 2023 SaaStr Annual featured a combined 60% women and multicultural speakers and have had over 60% women and multicultural speakers at each SaaStr Annual since 2018, and we hope to do even better in 2024!

Our core goals and values at SaaStr include:

Putting on the most inclusive events in the industry and

Being as inclusive a community as possible.

At Saastr Annual, we hosted an Enterprise panel of AI leaders to share their experience and knowledge to help others understand how big companies think about and leverage AI. Sure – the rise of ChatGPT has gone mainstream for consumers and smaller companies, but what about the big guys?

While the first generation of Generative AI is great, it’s not quite ready to solve Enterprise problems.

So, where are we now in the adoption cycle for the Enterprise world? 

In this session, we brought together:

• Douwe Kiela, CEO of ContextualAI
• Benjamin Mann, co-founder of Anthropic
• Arvind Jain, CEO of Glean
• and Sandhya Hedge, General Partner at Unusual VC, 

To help us figure out how to sell GenAI software to some of the biggest organizations in the world. 

The fifth SaaStr Europa in London will attract 3,500+ SaaS executives and investors, a superb selection of speakers, and endless opportunities to network in June of 2024.

As part of the SaaStr community, our partners are an integral part of what makes SaaStr the top resource to help companies of all sizes scale and grow their businesses. We would love for you to join us in London!'

For Europa, we are offering a wide range of exciting opportunities for our partners. Download our prospectus today to learn more about our exciting sponsor opportunities. 

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There’s so much debate on social media and elsewhere on bootstrapped vs VC.  Bootstrapped you maintain control, and the unit economics.  But many see it as so much harder.  And it’s almost always longer. VC can let you go faster, but it can become an addiction.  And the dilution all-in generally ends up being 60%-70% by the time you approach an IPO.

The debate misses a simple, clear Third Way: Just Raise One Round.

A few folks that have done this, more or less:

• Klaviyo.  Now worth $8 Billion, they mainly just raised a seed fund and didn’t raise material additional capital until the pre-IPO phase.
• The Trade Desk.  Now worth $34 Billion, they weren’t sure how big it would get, so they raised just one core VC round.
• Zapier.  Raised one core seed round, and then got to nine figures of ARR.
• Veeva.  Raised single digit millions, worth $35 Billion today.

The “lamest” is Fake FUD.

But the thing is, it works. Up to a point.

What is Fake FUD?

FUD is Fear, Uncertainty and Doubt … that isn’t true:

• “They just lost Google as an anchor customer”
• “We just beat them out for Facebook”
• “Their mobile product crashes all the time”
• “They had a huge security breach”
• “They were down for an entire day last month”
• “They are running out of money and couldn’t raise a Series B”
• “Their product isn’t ____ compliant”

In competitive situations, FUD does work — at least sometimes. It is generally presented in a negative fashion, and because it is, it can backfire. A lot of prospects will see it as smarmy and unseemly. But others, struggling to decide which vendor to chose, will prefer the Least Risky Vendor. And here FUD helps them decide, with limited data, which vendor is the least risky.

FUD is frustrating, but Fake FUD is worse. It’s stuff sales reps just make up. Some prospects will test it out to see if it’s true. But some won’t …

You need to develop Counter FUD. Counter FUD to the truth is a lot of work as is it. Counter FUD to Fake FUD is harder to plan for, until it becomes a pattern.

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