Do Sales Execs Need to Be Micromanaged? It’s Complicated - The Entrepreneurial Way with A.I.


Tuesday, April 2, 2024

Do Sales Execs Need to Be Micromanaged? It’s Complicated


So a few stories from the past few weeks reminded me of a meta-challenge in managing a sales team in the founder-led sales:  so many sales execs need to be micromanaged, at least up to a point.

It’s not just me. Sam Blond, CRO of Brex made a similar point at our SaaStr Miam super meet-up:

You do sort of have to micro-manage sales reps, from SDR to AE.  At least until you have a VP of Sales.  Then, your VP of Sales will figure it out.

And that’s one of the many things that makes the founder-led stage tough.  Yes, some founders are micro-managers.  But not most of the good ones in my experience.  Most of the good ones want to hire great folks and just … get out of their way.  Let them do their thing.

But you have to make sure:

  • The calls are made.  Or not enough will be.
  • The outbound actually happens.  Or it sort of won’t, if it’s harder than other activities.
  • The follow-up happens.  Or the deal will be marked Lost when really it might have been won.
  • The contracts are reviewed.  Or crazy deals and crazy discounts will work their way in.
  • The commitments are locked down.  Or customers will be told the product can do things, and that they can be onboarded, in ways that … aren’t realistic.  Or even possible.

This unfortunately requires a fairly large degree of micro-management.

Take a look at this recent CRO Confidential with Sam Blond and Ashley Kelly, VP of Global Sales Development at Ripping.  You can learn so much from this conversation.  And one thing is just how organized, and really, micro-managed, a strong SDRs team is:

And a few recent stories:

#1.  An old member of the Adobe Sign / EchoSign time shared with me a story at our recent Miami meet-up.  Right after I left Adobe, one of our reps signed a $77k deal with a Big Customer.  But not for a year — forever.

This was a partner I’d been working with for years.  In the early days, our product wasn’t ready.  Later, it was, but the timing was off.  They were ready the third time.  But it was a gap when I wasn’t there, and we didn’t have good sales ops controls.  And so the AE that took the deal closed it in the way that benefitted them, but not the org.  A $77k deal was great for this AE.  But forever?  For 100 years?  A terrible deal for the company.  My old colleague had to painful rework the deal — to $500k a deal.  Not $77k forever.

#2.  A sales rep at a portfolio company gave unlimited data to a new customer he shouldn’t have.  Because he was also consulting to that customer in his side hustle.

Ok this one is a bit unusual, but it demonstrates the point.  At a portfolio company, a top rep signed a $100k deal that included a certain amount of data usage.  But he gave the customer a contract for unlimited usage, the same as $500k+ customers.  Why?  No one could figure it out at first.  But it turned out, he had a side consulting business.  And this $100k customer was almost paying him in that business. The rep had hacked the contract and system to provide the same terms a $500k+ customer would get for his side hustle client.

This stuff is common.

In fact, as my old VP of Sales said to me recently: “The only reason you didn’t used to see this stuff was because I handled it for you.” 🙂

The real point here is I know most CEOs don’t have the background, time or energy to truly micro-manage in the founder-led stage.  That’s OK.  Just … do more than you are doing.  Just do more.  Get more involved.  Listen to most Gong calls.  Join more meetings. And importantly, track more metrics.   Just do a little more than you are doing now. You’ll see benefits.

At least, until you have a great VP of Sales.  Then let them make the calls here.

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Jason Lemkin, Khareem Sudlow