Are You Interviewing 50+ Years Young SaaS Veterans? You Should Be.

SaaS as we know it probably started in 1999.  Salesforce was founded then, NetSuite just before that.  SurveyMonkey was founded in 1999, one of the few SMB survivors of that era.  There were apps before that (e.g., WebEx was founded in 1995), but Salesforce kicked off the current era, and is the biggest player in SaaS.

That means, especially if you are HQ’d in the Bay Area or have or are opening an office there … the market is flooded with folks with up to 20 years of SaaS experience now.   That’s a lot of experience, especially if you are a first-time founder.

SaaS: Maybe Plan for 30+ Years as a Founder

Certainly, the playbook has evolved in the last 20 years.  The software sure looks a lot different:

But not that much in terms of overall approaches to scaling has really changed, so long as you have kept up with technology changes.  Inside Sales teams didn’t use to have products like Mixmax or Salesloft or Chorus or Gong.  But they still sort of are structured the same way as a decade ago.  Demand gen tools have evolved dramatically, but how to move prospects down the funnel is pretty similar.  Etc. etc.

The point is that the strategies do change every 5 years or so in SaaS, and technologies evolve at a similar pace, but so long as you keep up with those changes, you’ll collect an incredible playbook over a decade or more in SaaS.  And likely keep getting better at it if you stay agile.

Below is a quick chart of a recent example of bringing in two 15+ year SaaS veterans into a start-up as VP of Sales and VP of Marketing.  Running the playbook the third time.  And growth not only almost immediately ignited from flat … but became … regular.  Almost boring:

Youth no doubt brings some fresh perspectives and approaches.  Having that is powerful.  Experience often brings too much “my way or the highway-ish”, or worse, a reluctance to embrace what is unique and different in each company’s distinct culture.

But goodness, especially if your team is pretty young and raw … you really want some veterans on the team.  And for the first time in SaaS, there are tons of them out there.

In SaaS, it really is a playbook.  Find a few VPs or ICs for your team that want to run the playbook again, just even better.  That are still a bit young at heart, but wise in experience. That may be the best combination of all in SaaS.

If nothing else, challenge yourself to interview several decade+ veterans for each open position.  Even a few 20+ year veterans for a VP position.

Adding that DNA to your team?  Magic.  You don’t yet know how to do it, most likely.  They do.

And as part of that, don’t just bring in folks that are 40+ to interview.  Bring in folks that are 50+.  I know some of you may be hesitant (even though you know it’s wrong to think that way).  Don’t be.  SaaS is 20 years old.  That means the best folks of the 50+ years young SaaS veterans will be the wisest, most practiced folks you can find.  That’s a gift.

And force yourself to construct a team that is diverse in all vectors.  Including age.  A heterogeneous team is not just powerful, but resilient.

Published on May 25, 2019

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