So backstage at SaaStr Annual this year, and in a number of other conversations since, I’ve had a chance to get a few quiet moments with maybe two dozen top CROs and VPs of Sales.

I’ve asked all of them what’s really on their minds.  

Yes, macro issues come up, and how they have to sell to more stakeholders now, and sales cycles are longer.  But the best long ago adapted.  A tougher selling environment happens, It just is what it is. The top CROs and VPs of Sales don’t complain about macros. They adapt to them.

But 3 issues have come up again and again, that CROs don’t want to talk about in public.  That they don’t want to be on the record about.  Because they’re triggering, or in conflict with the LinkedIn Vibe.  But they talk about it backstage.

The Top 3 Frustrations of Top CROs Today:

#1.  Sales Folks Just Won’t Go Back To The Office.

This was the #1 concern and complaint I heard from so, so many CROs.  Many although not most CROs are back to the office themselves.  And they don’t care where there top performers work anymore.  But the rest?  Almost all of them think it’s critical sales reps outside of the Top 10% work from the office at least 2 days a week, and ideally 3.  They also don’t think remote onboarding and training and culture is working well enough in sales.  But they’ve thrown up their hands in many cases.  No matter what the company mandates, folks still won’t come in.  And they see this as the #1 thing impacting sales — that they can have an impact on.  They see it in the numbers.  Folks outside of top performers are just less productive from home, in large part because they’re not trained as well and pushed as much.

#2.  Even Though There Are a Ton More Candidates Looking for Jobs, There Aren’t Enough Good Candidates.

In some ways, this concern is as old as time eternal. There never are enough truly great candidates, even in downturns. Yes, layoffs have reached recent peaks and many folks are in the market.  But top CROs tell me first, the best folks are harder to recruit now because they don’t want to leave something they are good at in tougher times.  Leaving feels riskier, even for a seemingly hotter startup or better work environment. And second, that — and this may be triggering, I admit — many CROs (and others) just don’t want to hire many of the folks laid off.  Many CROs see sales execs laid off in smaller layoffs (vs. mass layoffs) as sub-mid pack on average.  This certainly isn’t always true, and someone that struggles in one sales role can crush it at another.  The best CROs for sure take chances here, and everyone will overlook one rough stint if a sales exec had a good run before that.  But there is some truth here.  When layoffs come in sales, it’s often to the lowest performers.

In any event, CROs don’t think finding great sales talent is any easier today, even with more nominal candidates in market.

#3.  CROs Feel Like Customer Success is Phoning It In From Home, And They Have to Do More and More Of Their Job

Ok this one may be the most triggering of all, which is probably why few say it on LinkedIn or Twitter.  But so many CROs and VPs of Sales tell this to me again and again.  CS working from home … doesn’t work.  Not enough.  So many CROs, at top SaaS companies you’ve heard of, are taking on onboarding, QBRs, and much more post-sales themselves than they used to.  Because they just don’t see it getting done.  I see this across my own portfolio of investments, too.  This is different than wanting to own upsells, or renewals.  This is feeling they need to own onboarding and post-sales follow-up … because it’s just not getting done.

Please don’t shoot the messenger.  I know many will challenge all 3 of these points.  But — they are the tops on the minds of many of the Top CROs I’ve talked to recently.


On a related note, take a look at our top CRO Deep Dives here:

SaaStr Deep Dives With 100+ of the Top CROs in SaaS! From Atlassian to Zoom to Cloudflare to Bill and More!

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