30+ SaaS CEOs Share The Signs Their First VP of Sales … Just Wasn’t Going to Work Out - The Entrepreneurial Way with A.I.


Saturday, February 12, 2022

30+ SaaS CEOs Share The Signs Their First VP of Sales … Just Wasn’t Going to Work Out


So perhaps the first SaaStr post that generated a lot of controversy was “If Your VP of Sales Isn’t Going to Work Out — You’ll Know in 30 Days”.  The point of the post wasn’t that a new VP of Sales can get everything done in 4 weeks.  But rather, that you should see improvements ASAP.  1 or 2 new, better reps.  A few stuck deals that finally close.  Etc. etc.

A lot of veteran SaaS revenue leaders protested, but most of them, upon reflecting on it, came to agree the point was right.  A new VP of Sales doesn’t always double sales in 30 days — although it can happen in SMB sales.  But they do move the needle.  They don’t just talk.

As an update to that classic post, I asked founders what were the signs they first saw … that a mis-hired VP of Sales wasn’t going to work out.  I’ve collected them below.  If you think you’ve made a mishire, but aren’t sure, take a look at the list below.  These are warnings signs.

“Instead of learning what was already working and earning trust of existing sales team Brought in the exact sales script and process that worked at their last company Lasted less than 60-days” — Andrew Gazdecki, CEO Microacquire.

The old playbook does help, but every great VP of Sales knows they quickly have to evolve it to any new role.  A mediocre VP of Sales … doesn’t.

“First order of business: let’s buy a Keurig for the sales floor.

Second order of business: never learn the business, pricing, names of reps, or anything else.” – Ryan Doyle, Magic Sales Bot

Ok I do enjoy the Keurig so not sure I’m there on the first point.  But the second one is spot on. You can laugh, but so many VPs of Sales I’ve seen fail in startups never really understood the business, the pricing, or much else.  Why?  They are just trying to run a process.  That can work sort of OK in bigger companies, when the job is dashboards and pipeline.  But it doesn’t remotely work before $10m-$20m ARR.  If ever.

“Narrow scope lens rather than wholistic lens. Secondarily not metrics focused.” — Paul Tyrrell, Founder, Field Insight HQ

A VP of Sales can fail by only caring about metrics and process, and not the product and distincy customer needs.  But they can also fail if they can’t get their arms around what metrics matter.  More a risk in a very stretch VP of Sales that’s never owned the overall ARR / bookings number.

“Can’t source and/or close a single deal” — Julien Codorniou, Felix Capital

OK don’t laugh at this one because it’s real — and common.  It can take 2 different forms in my experience.  If you hire a VP of Sales too early and hope they can jumpstart sales, it’s often too early to bring them in.  They close nothing.  And almost worst, and more insidious, is the VP of Sales who joins something with some momentum — that doesn’t add anything to that momentum.  They claim credit for everything happening, but don’t add anything to revenue.  Their job is to tilt the curve.  Not barely maintain it, but with more expense and resources.

“Prev jobs all < 2 years and trading off those logos . 1- 2 times can be fit/ other co issues. No long term employment = better at selling themselves than a product or service. Always a deal that’s “about to close”, not enough top of funnel activity.” – Aanand Radia, Education Investor

A great VP of Sales probably does have to have stayed one place for long enough to get promoted, hire their first team, and see the full cycle.  That takes 4 years.  More here.

1. Doesn’t recruit any of their own people

2. Promises unrealistic deals/customers early

3. Their first sales pitch. If you talk 10x > than you listen, easy to know it won’t work out — Jonathan Lacoste, Space VC

Any great VP of Sales — job #1 is recruiting.  If they can’t recruit ASAP — in their first 30 days — it’s usually hopeless.

“Ability to recruit top talent and has a network that follows is the #1 signal. Talent is the bottleneck for all exec functions and early leading indicator on success or failure is recruiting gravitas.” — Joel May, Bridgegate

An amplification of the prior point, but a good one.  50% of the job of a true VP is recruiting.  And VPs of Sales have to recruit more talent than any other role.  So they are always recruiting.



conflict image from here

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Jason Lemkin, Khareem Sudlow