A Year and Half In Running the SF Customer Success Meetup

I assumed the role of organizer for the San Francisco Customer Success Meetup about a year and four months ago. While I spend most of my “organizer time” looking for speakers, I took the opportunity to volunteer myself for a speaking slot this month, and led a talk, “Customer Success: Lessons Learned after 4 Years In.” Since the talk was a bit retrospective, I also started thinking nostalgically about this whole meetup thing I took on.

First, let me tell ya, I am an introvert in the classic sense. After I accept an engagement, I go through all the phases Elizabeth Kugler-Ross describes after experiencing trauma, though I willingly and voluntarily to do it over and over. In the end, I really enjoy speaking. However, when I am done, I hole up in my hotel and drink tea in cloistered, robed silence like an explorer returning from expedition, completely spent. When I am “off,” I am off.

In 2014, I decided to take a stab as SFCS meetup organizer because I was involved in a few other meetups related to my field (Open Source CMS and web development). I thought it would be a good opportunity to learn about the relatively new focus on Customer Success, especially because it was in my job title. It was my first attempt at such a public-facing and ongoing commitment.

At the first meetup I organized, about 20 people came, and we met at my company’s office to discuss onboarding. Since then, I now have a few co-organizers who help, and we rotate the meetup between five or so different locations (much to the relief of our respective office managers). Our membership has grown from 70 to 700, and average attendance hovers around 50-60% of RSVPs, so about 60 people make it each time. Returning meetup attendees make up about 30% of the crowd, although I am seeing more of the same faces within the last six months.

I continue to make small tweaks and try to find a mix when choosing speakers. My ideal two-speaker lineup is: someone new to Customer Success, sharing some problem or struggle, followed by an expert who shares a related case study. Then discussion ensues, which is the highlight for me. It’s best when it is a conversation, a chance to mentor and to learn. There are enough opportunities in life to be talked at by experts, where no one wants to open their mouths and be thought stupid. Not at my meetup. Lame-o.

I try to line up speakers a few months in advance, and have a short set of bullet points I send to help set the context. While speakers range in style and content, each speaker gets about an hour, including discussion time. I continually encourage/harass the attendees to speak, and am delighted when they come through for me. I like giving people who may not have the chance to do presentations some stage time.

It’s also become my experimental art project. I have been going to meetups for years — they can be awesome or painfully disjointed and dull. I respect my attendees, as I know they are leaving work to attend ANOTHER work-related event, so I want to make it as fun as possible. A few months ago, I did my best to get everyone to dance. I find the dumbest joke I can to end the meetup. I send irreverent and (hopefully) amusing blast-email to the list that wouldn’t make it past my own scrutiny at any job I have ever had. It helps my writing and editing skills immensely. I still seem to send at least one wrong date or typo in about every update, but the group lets me know and always has my bock.

Yeah, that’s the lame humor you are in store for at my meetup.

The result is that I have met an amazing group of people, whom I just want to help and serve more and more. There are people looking for work, starting new jobs, struggling with their current jobs, starting new companies, launching new products, and my heart just aches for them to do well. It might be because I am maturing and turning into an old mushroom, but I have this sense of paternal protectiveness. I meet a few people each month for coffee to discuss whatever is going on in their worlds, and have a complete rockstar I mentor more regularly. It’s unexpectedly become the most fulfilling part of doing it.

I have also been able to meet and learn from people who know more than me. That was my main reason for doing this, and being able to pick people’s brains has been invaluable. The openness in Silicon Valley to help each other impresses me greatly, and the meetup has been a great place to put this generosity into practice. Being able to speak to those who have attempted ideas I am considering and sharing their battle stories has saved me and my company thousands, possibly trillions. Well, no — thousands is right.

It isn’t without it’s challenges. Finding good speakers, handling last minute changes, politely declining misaligned requests all make for occasional tough moments. If I don’t dedicate roughly ten hours per month to keep things moving, I have ended up scrambling to get a speaker or a location, so some event-planning discipline and muscle has had to be built.

I hope that this meetup is becoming more than a monthly thing I do. I hope that the people who attend are connecting and making bonds outside of the events. I hope that people are using it to help others and to ask for help. My concern when planning the initial events was if there was a “there” there; was there a community outside the annual Customer Success conferences? I believe there is, and I hope that I have been a part of lighting a fire in the community that continues. And I am really glad I stepped outside of my comfort zone to be a part of it.