So we’re back for “real-world” / IRL events.  After 6+ mega-digital events including doing the 2020 SaaStr Annual digitally, the 2021 SaaStr Annual is back in the SF Bay Area Sept 27-29.  And boy we’ve learned a lot over the years.

It started off by accident — we did a meet-up in 2013 as an experiment, with no content.  And almost 400 folks came!  Then we did a second meet-up in 2014 with a little content, and it went well.  Then 2015 was the first SaaStr Annual, with ~1000 folks on site (more on that here).  Fast forward to today, and we’re planning the 7th SaaStr Annual for 10,000 attendees.  It will be the largest non-vendor event in the world for business software, by far, and perhaps the one really Tier 1 B2B event this year.

But all this was an accident, and personally, back in 2013 and 2014, and even 2015, I knew nothing about events, other than as an attendee.  I knew what I liked about Dreamforce, Boxworks, etc. — and what I didn’t.  So the first plan was to do try to somehow do better than those events at least in part, both in focus and in experience.

A look back at our first big (and back then, pretty non-diverse) event, SaaStr Annual 2015:

So what have we learned?  Here are our top 10 secrets.  Some aren’t really secrets.  But most events don’t do these 10 things.  Do as many as you can, and you’ll probably have a pretty good event.

Secret #1: most moderators are truly terrible. Start there. A great moderator can turn an OK panel into a very good session.  This part is hard.  Just putting on an event is hard enough.  Picking keynotes is hard enough.  Then you have to make every panel interesting, too?   Yes, you do.  Otherwise, panels will be the most boring thing in the world.  But there’s a hack.  Start with a great moderator.  She or he will know how to make the panel interesting.  Even if it isn’t full of all-stars.  Even better — pick a great moderator than knows 1 or 2 of the panelists already.  That rapport will make the session even better.

Secret #2: most CEOs do not want to be interviewed by their VC board members. Those are generally low-rated.  This took me a while to figure out, but most successful CEOs do not want to be interviewed by their board members.  Well, they don’t mind, it’s just they are … guarded.  These are almost always our lowest-rated sessions, even if the CEO is super popular herself.  Very early angel investors sometimes are OK.  But being interviewed by your “boss” is just awkward, not done right.  Most VCs don’t see it in themselves, but they are a bit patronizing in their relationships with CEOs they invest in.  You want a fireside to be relaxed.  Try to skip the Board member as the interviewer, where practical.  1 or 2 is OK.

Secret #3: everyone >wants< to be on “the main stage”.  But what they >need< is to be on a packed stage.  If you are going to have more than one stage, you have to load balance.  I know every speaker wants to be on the main stage.  But if the session isn’t > 60% full … it will feel empty.  No one likes that.  Better yet, have no main stage.  Just have 2 stages.  Try to get folks to pre-register for sessions, and just put the more popular speakers on the slightly bigger stage.  But don’t make a big deal out of it.  Nothing saps the energy from a room more than a half-empty set of chairs.

Secret #4: you >can< build a diverse set of speakers. Start early. Ban Manels. Tell panel leaders they have no choice. No diversity, no panel.  It took us a while to figure this out, but in 2018, we had 60% women and diverse speakers, and we are on track to match that in 2019.  Start early.  Set clear goals.  And don’t compromise.  Especially on panels.  When we baned Manels in 2016, we got a lot of pushback.  But that faded in 2017.  We don’t get any No Manel pushback anymore.

Secret #5: a smaller event that is packed is much better than a larger event that isn’t. Much, much better.  This is almost error #1.  A bigger event is not better, unless it is clearly better by being bigger.  We had our first SaaStr Europa this June in Paris with 1,600 registered.  Yes, that’s big, but much smaller than the SaaStr Annual.  And yet — it was our highest NPS event ever.  ~90 NPS from speakers, sponsors, and attendees.  That’s way hard to do.  Bigger is not better, unless there is a clear reason to do it.  Your event does not have to grow each year.  Instead, just make it better.  Don’t get sucked into needing attendance numbers to grow each year.  It will overwhelm your team, fatigue your ability to deliver enough content, and exhaust your attendees.  They just want to network, have fun, and learn a few new things.  That’s enough.

Secret #6: for smaller sessions, ask the speaker what they are most passionate about. just have them talk about that.  OK, this is my personal #1 secret.  Want to avoid boring sessions?  Ask a speaker what they are most passionate about today.  Absent a better idea, have them speak on that.  Make them, in fact.  No matter what, that’s a better idea than the boring product commercial or other thing they had in mind before you asked.

Secret #7: have a shorter event. No one wants to go to a 3-day event, or even a 2-day event, with rare exceptions.  This goes hand-in-hand with Secret #5.  Have a smaller event, and importantly, have a shorter event.  Very, very few events need to be longer than a day.  Add an extra half-day as you scale, so there’s a reason to come in the day before, and that’s usually enough.  Grow from a great half-day, to a full day, then maybe to a 1.5 day event.  But you aren’t Dreamforce.  Cross the 1-1.5 day line, and your NPS will likely fall.  Your costs will go way, way up (multi-day events get much more expensive per attendee).  And no one will get more out of it.  A great half day or 1 day event is a wonderful thing.  See Paris Europa 2018, above, as a perfect example.  It was one full, long day.  It was great. It will be 1.5 days next year for 2,500 folks. And that will be enough.

Secret #8: if you think you’ve already heard that speaker before, so has your audience. Maybe search wider.  Everyone tries to get the same speakers, for a variety of reasons.  One is everyone wants the popular speakers.  But the other reason is a sort of laziness.  If Linda spoke at another industry event, well, yeah, you may be able to get her, too.  But look harder.  We are all bored of hearing the same speakers again and again.  At SaaStr now, we make speakers wait 2 years to speak again (with some narrow exceptions), and we don’t allow recycled content.  Going with recycled content and recycled speakers can be the path of least resistance.  It’s the easiest way to program an event.  Resist.

Secret #9: if you think it’s a cookie-cutter event, so will they.  Events are exhausting to produce.  They are expensive, you can’t slip a date, and it’s hard to find veterans that have done it before.  So what happens is, folks revert to “check-the-box” mode.  Just get it done.  The same boring venue.  The same turkey sandwich.  The same birds-of-a-feather.  The same hotels.  It’s so hard just to produce even a cookie-cutter event, that you’ll find it hard to do more than that.  Intertia will push you to a mediocre event.  Don’t let it.  Because if any element feels cookie-cutter to you, it will to the audience as well.  You can’t mix everything up.  But pick at least 2 or 3 elements in each event and make them special.  Make them yours.  Make them authentic.

Secret #10: never let anyone talk about their product on stage.  If nothing else in speaker content, follow this rule.  And it’s hard.  Every speaker will want to talk about their product.  Not necessarily themselves, but their product.  Nothing is more boring, generally speaking.  At least, make them talk about the impact of their product.  Or make them bring up 3 of their own customers or partners on stage with them.  Or talk about the early days.  Or the tough times.  Anything but a product commercial.  Anything.  Again, inertia will be your challenge.  It will a lot easier to get speakers to come to talk about their own products and companies … than other things.

Good luck!  Events are hard.  At scale, they may be the most tiring thing I’ve ever done.  But push through.  Because there are way, way too many events these days.  Too many meet-ups.  Too many of everything.  Push through and do something special.  At a minimum, use this checklist.  It will make your event better.  It’s what we’ve learned the hard way.

(note: an updated SaaStr Classic post)



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