Alright, we're going to have some fun with this week's edition of SP.
After over a decade working in startups/scale-ups, I have my fair share of crazy stories and this week I'll be sharing two of those with you...
Oh, and if you like this sort of thing, be sure to reply and let me know. I want to make story time an ongoing part of SP's weekly content.
CIOs Don't Want Pics of Your Dog
I spent a few years of my career as an SDR manager at two different companies, one a Series B startup and the other a late-stage Bay Area "unicorn" that later went public.
I could probably fill an entire book with stories from my time leading young, hungry SDRs, but there's one story that really stands out.
An SDR on my team was working on inviting executive prospects to meet at an upcoming trade show. Using ZoomInfo, she was able to get the cell number for the CIO of a Fortune 500 company (one you've definitely heard of). I guess she thought texting him pics of her new puppy would soften him up and get her a big meeting.
Wrong!
I honestly had no idea she was in the habit of texting cold prospects with pics of her pets. I found out because I got a call one afternoon from the Regional VP whose team owned the account relationship.
This was the convo:
"Jesse, you're lucky I've been on a plane from NYC to SFO for the past 5 hours since it's given me time to calm down a bit before calling you. WHY THE F#@K IS YOUR TEAM TEXTING DOG PICS TO PROSPECTS?!?"
I learned from the RVP that this CIO was so upset about the "unsolicited dog pic" that he put a memo out to the entire IT organization with an order to blacklist us as a potential vendor partner.
There was an active deal and the director-level champion informed our team that they would not be proceeding due to the unprofessional nature of the outreach.
Damn...
I learned a lot about leadership and management that day and I took ownership of my part in the fiasco. As for the rep, she got a LOT of coaching and enablement, but ended up leaving a few months after. She's still in sales though.
At this point, I also decided my goal was to get back into an IC role. SDR leadership can be rewarding, but it's one of the hardest and most thankless roles in the software business.
By the way, all was not lost; if I recall after some time passed, this CIO softened his stance a bit and revoked the blacklisting, which allowed the team to take another pass at doing a deal. No idea if it ever closed though.
Moral of the story? Keep an eye on what your SDRs are sending and always pause and consider what you are about to send to a prospect, especially if you are reaching out to execs.
Getting Access to the Decision Maker... In the Men's Room
Okay, here's one that I'm not super proud of (or am I?). It's the 100% true story of how I got the verbal for a $100K+ annual SaaS deal and closed it a week later. Great story right? Well, I should mention that this was because I cornered the CTO and decision maker in the men's room.
Here's some background context so you don't assume I'm in the habit of following my prospects into the John.
At the time I was the first AE hire at a Seed series startup in Austin selling a SaaS product for data streaming.
The VC firm who had recently funded us invited our team to attend their annual holiday party in downtown Austin. At the time, there were 10 employees at the startup, 8 of which were engineers and the Founders nominated me the lone sales rep to represent the company at the event.
Our lead investors had been great about helping us get intros to potential buyers within their portfolio and had connected us with a fast-growing startup in the legal tech category also based in Austin.
The conversations had been going well and we had buy-in from the DevOps team to move forward with a deal. However, we were waiting on Ken (not his real name), the CTO to stamp the deal and sign the order form. In the weeks before the holiday party, I had been calling Ken almost daily to find out the status of the deal and signature. I left him multiple voicemails and tried to work through my champions to get the deal finalized with no luck.
After making my rounds at the party, I decided it was time to head out. Before taking off I decided on a quick bio break since you never know what traffic in downtown Austin will be like.
As soon as I set foot in the men's room I recognized him from his LinkedIn pic, standing at the sink. Now was my chance.
"Ken! Jesse Woodbury, with [redacted] great to meet in person!"
Prior to this I hadn't had much interaction with Ken so there was a 50/50 chance he was going to punch me in the face. Luckily, he was super friendly and had a great sense of humor about the fact that we were meeting in the WC.
"Jesse! I got your voicemail, I'm so sorry, we had our board meeting recently and we are in the process of our SOC 2 compliance and I went on PTO, I've been meaning to return your call."
After a few minutes of catching up in the dimly lit restroom, he agreed to finalize everything that coming week. We opted not to shake hands considering the circumstances and he was on his way.
A few days later the e-signature hit my inbox and I met Ken and his team on-site at their HQ a few weeks later for onboarding.
There's a lesson here. As a Sales Player, you've got to take every shot you can get, even if it means a few seconds of awkward conversation in a restroom.
I hope you enjoyed reading this as much as I enjoyed writing.
Thanks for reading and let me know if you'd like more stories like this!
-Jesse