How ME Stepped in to Produce SaaStr Conferences

7 stages, 250 speakers, 10,000 attendees, hundreds and hundreds of content — all of this and more at this year’s SaaStr conference in San Mateo, CA. This event is no task for just anyone, it takes an experienced and methodical event planner and her team to produce such a large-scale event. That team? Montgomery Entertainment, LLC.

Jason Lemkin, CEO, and Founder of SaaStr was recently interviewed by Nathan Latka, CEO of Founderpath. In this interview, Nathan asks Jason about SaaStr and what it takes to produce SaaStr conferences. The SaaStr team consists of 10 employees — 5 in sales and 5 in marketing — doing 25 million in revenue. In addition to these 10 full-time employees, the team “aligns” with core agencies (for better or for worse, Jason adds) that are close to embedded in-house: “These aren’t just random agencies — they’re not agencies that just come and do little tweaks — these agencies come to daily scrums.”

So what does Jason mean when he says they work with agencies “for better or for worse?” For the most part, the SaaStr team works with agencies for the better, but it took Jason 4 years to bring Montgomery Entertainment, LLC, notably Ashley Montgomery, as the Executive Producer of all SaaStr Conferences. Before ME, LLC, it wasn’t always smooth sailing. When asked how many event agencies the team went through before Ashley, Jason responded, “Two quit, one fired us, one said they’d work with us but didn’t do their due diligence on how much work it was and backed out, and then another quit a few weeks ago. Montgomery Entertainment comes to the venue and sets up everything which takes a week and a half, they’ve gotta manage all the AV, recordings, food — they’ve gotta feed 10,000 people! DJ’s, and they have hundreds and hundreds of vendors to deal with.”

Jason’s discovered that when you’re doing events to scale, you have to know how the function works yourself. He gives the example of a software release and how you can postpone it a week, or even a month, but you can’t just postpone the date of an event at this scale. He mentions when he hired mediocre people they didn’t just fail to get it done, but they all lied about it. SaaStr experienced a 10-million-dollar mistake from an event planner who said she booked the venue but didn’t. Jason likes to be a macro-manager, he likes to be hands-off, hire great people, and get out of their way! But Jason faced the question of whether you can be a macro-manager and be hands-off if you don’t know how the function works yourself. When you hire someone to fulfill a role that you don’t know well enough yourself, it’s super risky. Not wanting to be anchored down to details, Jason didn’t learn about the details of event production and because of that, was not able to spot issues until it was too late. By realizing the importance of learning how event production operates, Jason was able to better communicate what needs to get done.

When asked more about the agency that has made SaaStr conferences a success, Jason notes that Montgomery Entertainment, LLC is “very, very good” at event production, and although it took him several years to find the agency, they’re really great.

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