Dear SaaStr:  What are some of the “ultimate sins” in marketing and sales and success in SaaS in the early stages?

My list of some bad ones:


  • Hiring any reps you wouldn’t buy from. This never works out in the early days. Later, once you have a strong VP of Sales, it’s fine though.  A bit more here.
  • Hiring a “VP” of Sales before you have 2 scaled reps and a repeating process. Never works out.  More here.
  • Crazy quotas. You can’t set folks up to fail 100% for sure. Especially the first few months, maybe even make their quota simply equal to their salary. Your sales reps need to eat.
  • Expecting a closer / in-bound rep to do out-bound. They can’t. You have to hand in-bound folks leads. They are no good at generating them.
  • Expecting an SDR to close. Hire stretch reps if you want, but someone without any closing experience likely can’t close at your startup no one has ever heard of. Unless the product is very cheap and the prospect is close to closed already.
  • Hiring just 1 rep. You can’t A/B anything and won’t have any idea why anything works.
  • Hiring reps before you close 10 customers yourself. If you can’t …
  • Hiring for the logo. Hiring someone from Salesforce, Box, Twilio, etc. not only won’t save you. It’s a negative. Those companies are way, way too big. With way too strong processes and systems in place. And, most importantly, infinitely stronger brands.
  • Hiring any reps who “don’t care about money”. Startups are a journey and you need reps that want to be on the journey. But if they say in an interview they “don’t really care about money” … well … they aren’t sales people. Maybe OK for customer success.


  • Hiring too junior of a marketing person as your first marketer. If they’ve never head a commit, or a number, they are too junior. Do not save money here.
  • Hiring a mediocre PR firm. $8k-$15k a month down the drain for nothing. Only the very best folks (and very best PR) is worth it.
  • Hiring a brand marketing firm. See last point. May make sense later, but this almost always is just throwing money down the drain in the early days.   A bit more here.
  • Hiring lots of “agencies”. See above. Get rid of this marketer.
  • Outsourced content marketing. OK, this is sort of OK as long as you don’t expect much. But if some 3rd party is writing your content, don’t expect too much. Including not too many leads.
  • Way too much SEO + SEM talk. Both are important, but in SaaS, both likely will be relatively minor sources of customers.
  • Hiring a B2C marketer for SaaS. Related to the prior point. The skills are not that portable.

Customer Success:

  • Hiring anyone in mid-market or enterprise CS that doesn’t go visit customers in person.  A lot of folks don’t want to visit customers in person anymore.  So be it.  Just don’t hire them to manage larger accounts.
  • Hiring anyone in customer success in the early days that talks all about process.   You really don’t need a ton of process in CS until $10m ARR, really $20m ARR in many cases.  (Also true in sales)
  • Hiring anyone in customer success that can’t give you 2-3 happy customers as references.  Go find out what they really did for these customers.
  • Hiring anyone in customer success that wasn’t an expert in the product at their last company.  That’s a sign.

(don’t do it image from here)

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