Dear SaaStr: Can A Great Sales Rep Sell Any SaaS Product?

Not really in SaaS. At least not well.

The classic “Sell Me This Pen” test still has value, even in SaaS. There is no perfect answer to this test, but it does show a salesperson’s ability to think, to convey enthusiasm, to understand a value proposition, etc.  It may have gone out of fashion, but I think it still shows sales smarts.

But I’ve come to learn that in SaaS at least, salespeople can be:

  • Good at Outbound, but not so much Inbound. Or vice-versa.
  • Good only when selling with a brand to back them, but not so much without one.  This is so important.  The playbook is so different when you are #1 or #2 in an established market.  Because the prospects already sort of know what they are looking for.
  • Good when selling — but where they have a lot of processes and support.  Many reps from larger SaaS companies, especially with mid-size or larger ACVs, melt when they have to do their own demos, answer tougher questions, lack the right collateral, etc.
  • Good when competing for budget, but terrible when competing with an aggressive direct competitor.  Sales reps trained in an environment without a strong, direct competitor often seriously struggle once there is one. It’s such a different toolkit, to sell against a very similar, aggressive competitor.
  • Good at selling products similar to what they know, but struggle to sell more complicated or vertically-focused products.  It’s really hard for most reps to transition into a more challenging or more complicated selling environment.  Be careful here.  As a rule, hire reps that sold something harder to sell and more complicated than your own product. Even if just a tiny bit more.
  • They also can be good at one price point, but often not at others:
    • A sales rep that is good at handling 50–100 leads a month and closing them quickly at a $3k-$10k price point rarely can handle all the skills necessary to close a $250k deal. Moving from one stakeholder to many is a very different skill set. As is managing a deal through a lengthy sales cycle vs. a quick close.
    • And vice versa. A skilled field rep good at $100k+ deals rarely has the patience, planning and organizational skills — let alone the speed — to close 10x as many SMB deals per month as bigger deals. They usually melt when they have to ramp up their volume, speed, and close rate.

So there are a lot of variables here. For the most part, controlling for (x) stage and (y) price point works. Hire a few reps that have sold at your stage and your price point that you also believe in and would buy from — that’s the trick in the early-ish days.

And a great VP of Sales and sometimes a great Rev Ops team can train a rep to learn new skills. So once you have a great VP of Sales, let her figure a lot of this out.  They’ll hire folks … you wouldn’t hire yourself in sales.  Up to a point, if you believe in your VP of Sales, you have to let them.

But whatever you do, don’t just assume because an AE was pretty good at their last role they’ll be good at your startup too.  You gotta dig deeper, and use the above as a checklist to start.

(note: an updated SaaStr Classic post)

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