My Best Advice for CROs/VPs of Sales That Are Ready to Be CEOs

Many of my favorite VPs of Sales are now becoming CEOs. Many. And I am so happy for them. Many SaaStr OG’s have pulled this off, and I’ve watching many from Sterling Snow, CRO at Divvy joining Redo as CEO, to our own Brendon Cassidy, CEO at HiveFive, pull it off.

I have one bit of advice though as you watch them go from CRO to CEO: it’s a much, much, much, much bigger jump from CRO / VPS than you can ever imagine.

And they agree.

It’s now all on the line.

And 95% of you have never actually shipped a production into production. Committed code. Dealt with a SEV-1. Or even know what a truly great CTO looks like.

You can do it. Just realize it’s 10x harder than you imagine. Maybe 100x harder.

Just because you sell it, does not mean you can build it. And leading a great team is not the same as going from 0 to 1.

The 11th SaaStr Annual will return in May of 2025! 

We just wrote up some of the sponsor & attendee data from this year's Annual, but here are the top 3 learnings, attendee-wise:

#1 - 57% of all attendees were VP level and above. 

So there are a lot of different attendee data points that are interesting from hosting 10 editions of the SaaStr Annual, but it's great to see this number go up YoY.  It's by far, the highest concentration of both CEOs and VPs of Sales and Marketing at any non-vendor B2B event in the world.

So if you attend in 2025 -- you're in good company :) 

#2 - 44% of all attendees come as a team, +70% come as pairs 

We’ve seen this consistently now for the last 2 years, that the majority of attendees come in groups. With 44% of attendees coming as a team — ie 3+ or more attendees from the same company, and +70% of attendees coming with at least 2+ people from the same company.

#3 -  Within attendee groups joining as a team, at least 1 was an exec

Maybe more interesting that ~1.5 of those 3 from a team attending are at an executive level. On the attendee side, it’s a point that more teams are coming vs solo individuals to help expedite decision-making and in-person time at events like a SaaStr Annual. 

All of this to say, if you're considering attending next year's Annual as a team, now's still the best time to do so. 

Early bird tickets are always the best pricing and about $1000 less than last-minute tickets.  So if you want to go for the least possible — now is the time.  You can bring the team for as low as $549 each now!  That will double by the time we get to May 2025.

Let me take a slightly different take on the question.

Maybe you are really asking – “Am I still on the hook if we hire a ‘real’ CEO to run the company? ‘Cause I’m tired/stressed/don’t really enjoy running this thing. I’d rather just be running product/coding/hanging out at events/whatever.”

My learnings and experiences are this: if you want your start-up to really make it … then you will be just as much on the hook as ever.

This new CEO, no matter how great she/he is:

• Does not understand your domain the way you do
• Probably, is more operational than strategic in terms of understanding the space
• Maybe, will never really see the future the way you do, only the present
• And maybe, can’t see the cracks below 5,000 feet and won’t know when and where and how to fix them.

If you bring in an outside CEO, and then check out, or leave … you will be seriously damaging the value of your equity. You just know so much at this point. Because you had to do it all, and learn so much, getting 10, then 100, then 1000 customers. Which is borderline impossible. There’s a reason most start-ups don’t get this far.

So don’t bring in an outside CEO to get some rest. Only do it if it increases your equity value, because he/she will make the company worth even more. Because if you want to win, you won’t be getting any vacation if you leave sub-$40-100m ARR.

We recently held a post-event SaaStr Annual executive de-brief to share some of the latest event data and trends we saw across all 100+ sponsors and 10,000 attendees of this year’s SaaStr Annual.

A lot of this proprietary data is I think too good not to share, and maybe help even give you a gauge on where at least some of your compatriots in SaaS trended for an event at this scale.

The average Super Gold sponsor received 470 qualified leads in 2024, up from 249 in 2023. 

A lot of VC advice is a bit self-serving. Not necessarily wrong, but self-serving. Is raising VC capital at a “too high” valuation a bad thing, as so many VCs say? It’s mixed.

There are risks with a too-high valuation — but also benefits:

A high valuation isn’t necessarily bad. It just has dangers. We’re seeing a ton of that now with unicorns that raised at very high revenue multiples that now are unfundable. But like many things, it’s nuanced.

© SaaStr 2024

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