Want to get outbound going, for the first time?  What almost never works, somewhat surprisingly, is hiring a Director of Outbound as your first outbound hire.

I see many startups want to add outbound, but not really have a lot of experience. They don’t know outbound, they haven’t done it, they don’t get it.  And especially, a new VP of Sales comes in without real outbound experience.  And finds they don’t have enough leads to hit the number on inbound alone.  So they naturally look for a leader to start, a Director of Outbound that has built and managed an outbound team before.

Why does this seemingly logical hire fail?

  • The proven Director of Outbound is usually all about process and never learns the product. That can work at scale but generally fails in the earlier days.  There isn’t a proven process at all yet to improve and build on.
  • They hire a ton of SDRs fast because it’s a numbers game, but no one ever really gets it right. You need 1–2 SDRs that deliver $1m+ of bookings from their inputs to first prove it works.  Maybe you can lower this a bit to $500k at first, to prove it out.  (Whatever the exact target, you prove out 1-2 SDRs can set up meetings that lead to a material amount of closed business).  But if you hire 8-10 out of the gate, no one ever figures anything out.  They book almost no meetings that close.  And it confuses everyone.  Tons of motion and energy, little to no actual results.
  • They often use trite, proven scripts and processes that aren’t right for your market and especially for a niche product without a brand behind it. That generic sales script often doesn’t work well selling to developers.  The “grab 5 minutes of your time” mass cadence to 5,000 hardly works when no one has heard of you.  Etc. Etc.
  • And most importantly — a Director+ of Outbound is often hired by a VP of Sales that doesn’t know outbound themselves. This compounds the issue.  A VP of Sales comes on that hasn’t really done outbound themselves, so they don’t really know where to start.  They hire a leader to get it going — instead of figuring it out first.  Crash and burn.

I see this Director of Outbound hired too early just crash and burn again and again. They hire a big team fast, that builds almost no real quality pipeline, but takes up a ton of time, money, and energy.

There are two exceptions, when it can work:

  • One, if your VP of Sales has proven themselves already, and/or has a proven background in outbound, and they want to make the Director+ level hire first anyways — well, let them. Back them. But otherwise, push back. Force yourself, your VP of Sales, and your sales team to hire 1–2 individual SDRs first.  And really help them and back them — and prove it out.  Outbound always works.  But only if you truly do it right.
  • Two, if the Director of Outbound is great AND is willing to start off doing it themselves, as the first SDR … for real … then I’d take that risk.  If they truly will be the first SDR themselves, and do it before they scale it.

But otherwise, wait until you have a proven SDR to ideally two — then go hire a leader. And half the time, that leader will turn out to be one of the SDRs you already hired anyway.  You end up promoting the best one anyway.

Sam Blond, ex-CRO of Brex, aligned on the same advice at a recent Workshop Wednesday on building your first outbound team.  He did hire a Director of Outbound first, that he already knew.  But — but — she was willing to be the first hands-on SDR herself.   So that’s an example of both exceptions to when it works, really.

That full convo here:

And at the risk of repeating myself, let me distill it down to one piece of advice: if you hire a VP of Sales without any true outbound experience themselves, don’t let them hire a Director of Outbound to start.  It just … never works.  It’s a Know Nothing teaching a Know Nothing.  Make them prove it.

Outbound Always Works. If You Do It Right. And You Put In The Time.


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