Alright, this is going to be one that the Joan Didion and Jeff Bridges fans out there can get behind. Initially I wrote up an entire post that was filled with “lessons” from my first month at Rattle. However, I don’t want Compstep to be an encyclopedia of sales tips and tricks. I will include content like that, but I also want this blog to highlight the human side of making big life changes. There are so many intangible feelings and emotions that go along with transitions like this, and I think capturing those and reflecting on them publicly is really important. Everyone has experiences like this in their lives, and it’s helpful to get inside a person’s head and go beyond just the technical aspects. So here is a reflection on my experience thus far followed by a few learnings from my first month at Rattle.
The Intangibles
No Regrets + Real Independence
First and foremost, I haven’t second guessed my decision once. It’s funny, I think that conventional wisdom holds that when someone moves from a “safe” job to a startup, there is always going to be this moment of existential dread. It’s that famous “head-to-palms” moment where the person says their goodbyes and suddenly they are all alone, exposed to the world, no safety net to speak of, evil creatures lurking in the shadows all around. I can’t say exactly why I haven’t experienced this, but my guess is that it has to do with something I touched on in my last piece: I thought about this for a LONG time. I spent nights agonizing over what it was I wanted to do with my life and what my next step would be. I had difficult conversations with my bosses, and sought advice from my mentors. Ultimately, I did a lot of reflecting (which people who know me know I am BIG on), and through that reflection I was able to identify what I really cared about. For me, what I really value is process over reward.
As a former D1 athlete, I will always come back to athletics. Maybe that makes me sound unsophisticated, but I don’t care. I think that sports teach invaluable lessons in life, so I will constantly fall back on those experiences. Through my reflection, I realized that I enjoyed swimming and rowing because I enjoyed the processes associated with them. I was a good swimmer and a good rower because I liked going to practice. I liked working hard with my teammates. I enjoyed spending hours every day in the boathouse. Best times and winning races of course helped fuel the fire, but I honestly enjoyed doing 10x300 freestyle best average or 3x10’ + 7’ erg (grueling workouts for the non-swimming/rowing crowd). Rattle is the professional embodiment of these athletic experiences. I am not here for the IPO, I am here because building something with a motivated group of people is awesome.
Second, I have found an incredible sense of independence working at a startup. Importantly, I don’t mean independence in a physical sense. Yes, I get to work from wherever and I don’t have anyone tracking my every move, but that isn’t the type of independence I am referring to. Instead, I finally feel like I am going down a path exclusively because I want to. If I were to look at my life through the lens of the Big Lebowski, up to this point I have been like a bowling ball going down the lane with the gutter guards up. I have had some wiggle room and could make a lot of choices for myself, but at the end of the day I was always going to end up at the other end of the lane knocking at least a few pins down. Now though, the gutter guards are down. That isn’t to say that it is all or nothing, but I am finally doing something solely because I want to. I found the startup world through happenstance in the middle of Covid and now I am committing to it full time. There was no external pressure, no sense of expectation from those around me, no pursuit of prestige, none of the metaphorical gutter guards that guided me into finance as a college senior. That is the sense of independence I am referring to. The kind that comes with choosing a job purely because it’s something that interests me.
The Tangibles:
FAIL!
This one may be a startup cliche, but it is true. Failing is absolutely encouraged at Rattle. Obviously we don’t set out to fail, but in order to establish a culture that supports risk taking and decision making, we also have to welcome failure. In my seat, I have tried so many different cold email methods (including modifying a Joan Didion poem…see below), many of which haven’t worked, but some have. I never would have discovered the methods that do work if I was afraid of getting on OKRs at the end of the week and telling the entire team that I didn’t book a single meeting.
It isn’t for everyone…yet:
One of the things that has surprised me most has been the emphasis on customer/product fit. I came into Rattle assuming that as an early stage startup we would take a meeting and sell to anyone that would give us the time of day. However, what I have realized (and appreciate) is that our leadership is aware that Rattle isn’t for everyone, and that’s okay. Eventually I do think that most companies out there will be using Rattle, but right now if we get a meeting and the prospect can’t figure out how Rattle will fit into their business we are not going to jam it down their throats. We will show them use cases, and try to ask questions in order to nail down their primary pain-points, but if at the end of the meeting they still don’t understand the value prop or they’re pushing back on the salesperson, then it might just be the wrong time and that’s fine.
This is the time when processes are built:
Coming from a huge company, I have never experienced the building of business processes. What I have learned over the last few weeks is that everything being done now has to be looked at through the lens of “does this scale”? Certain processes work in the moment, but what I need to consider is whether or not somebody just joining the Rattle SDR team will be able to replicate what I' am doing with minimal handholding. Additionally, building scalable processes is not the job of the CEO. It is the job of the individuals in each role. Thus, even though I am new to the SDR team, I need to be thinking about how to build and scale the SDR function within Rattle. I have a front row seat, so I know what is working, what is not working, what tools are available to us, and how best to utilize them.
Conclusion:
So that’s it for now. One month in and I could not be more thrilled to be at Rattle. In the words of The Dude there are inevitably many “strikes and gutters, ups and downs” to come, but that’s alright. I am here for the process, and the coolest part is that everyone around me is as well.
Joan Didion Themed Cold Outreach (which successfully booked a meeting)
I write [cold emails] to find out
What [my prospects] are thinking
What [PROSPECT NAME] is looking at
What [Integrating Slack/Teams with Salesforce] Means
What I want and What I fear
Figured an aspiring hippie like yourself would appreciate a cold email in the form of a Joan Didion poem.
Excited to connect.
-Andrew
Love the Jeff Bridges and Joan Didion references😉