Writing on the wall? How am I here again?!

I don't feel like writing a novel but have a tendency to do so since I think all the minor facts paint the picture but here we go.


I've been at the same company for a solid tenure and have risen through the ranks from SDR to ENT AE. From a "just went public company" back to private in one of the largest PE acquisitions of the pandemic years. I've seen so many phases and worked with so many great people, but the last major shift happened last year in the first RIF to hit sales, and luckily, I found myself a promotion to ENT AE with a piss-off 5% "take it or leave it" raise.


I had to work for someone who I wasn't thrilled to given their bulldog reputation. Forced to leave my mentor's side and start with a new manager. Then the new manager got canned because they pissed everyone off and eventually crossed the wrong person. Then, I went without a dedicated manager(and, more importantly, mentor) for months. I had no success in my NN accounts despite tons of hem-and-haw conversations and meaningless partner meetings, and the customer accounts I was given were honest trash. My one major account was in a legal battle as soon as I got it, the ARR eclipsed all of my other accounts. The other midsize accounts that hadn't been nurtured for 2 years (little to no upside) and i fought to squeeze out what I could. On top of that, I had a significant personal loss that I won't share more of due to fear of doxxing, but I've powered through and still managed to deliver rev for the company.


I finally got a new manager who I can tell is just not my style and has brought maybe 1 good idea to me since starting, and they, of course, don't know shit about the platform or nuances of our processes (pre-sales, legal, deal desk, collateral, tools, etc) as I have accumulated over my tenure. My prior mentor was a wizard both in our product space and everything X company. They were a true partner to my business and I'm still reeling from not having that still, a year later.


So here's the real dilemma: I don't want to leave (or be forced out) because I deeply believe the product and innovations we've made are game-changing. I've seen and felt the excitement of the direction of the product however, the GTM culture has taken a nose dive off Everest down to the Mariana Trench. CRO is clearly in panic mode, having delivered 3+ years of lackluster results against our targets and probably the target of being replaced, with this being a stain on their career as a C-level leader, and that panic is being equitably (LOL) spread across literally everyone. I've held on this long, and feel like if I can just outlast the next RIF (PIPs were handed out but I didn't get one, still "received" the message though), there will be a new dawn (see SaaS hangover from 2022-2024) to enjoy fruits of surviving economic austerity and continuing to apply and grow my knowledge in the space.


TLDR - another burnout story, this wasn't even close to a novel by my standards ;)

๐ŸŽˆ Mentorship
๐Ÿ™ Mental Wellness
๐Ÿ˜ค Conflict Resolution
11
Justatitle
Big Shot
6
Account Executive
the question of how you are here again is a simple fact of being in the game. Which brings one of my favorite quotes into play. "The problem with the rat race is that even if you win, you're still a rat"
TheColdestColdCall
Executive
3
Enterprise Account Executive
God I love this - stealing it. I'll make sure to quote "justatitle" for credit
Revenue_Rambo
Politicker
3
Bad MFer
Sounds like the orange monster of a company that I left a few years ago. If it is the same one things are only going to get worse based on conversations Iโ€™ve had with senior leaders Iโ€™m still connected with.
TheColdestColdCall
Executive
4
Enterprise Account Executive
Not Orange but regardless, sounds similar. Le sigh.
jefe
Arsonist
4
๐Ÿ
I haven't experienced this, but am inclined to agree with Rambo.
*le sigh* indeed
MRK47
Tycoon
3
Head of Growth
Unfortunately, believing in the product and innovation alone wonโ€™t enrich your daily grind. History is littered with innovative products that disappeared due to not being supported by the right GTM motion or strategic vision.

You mention 3 years of lackluster resultsโ€ฆ.thatโ€™s a pretty sustained path of decline likely amplified by misaligned leadership..to turn that ship around will likely take significant time, resources and a broad change in leadershipโ€ฆwhich means preparing yourself for worse times before they get betterโ€ฆ.without guarantees that youโ€™ll come out on the other side, do you really want to weather the storm for the next 1-2 years, constantly looking over your shoulder at a potential RIF / PIP while the business tries to course correct?

And naturally donโ€™t discount the value of working with a manager who youโ€™re fully aligned with and will act as a true partnerโ€ฆ..youโ€™ve faced challenges with your one major account and other mid-sizes ones (for reasons outside of your control)โ€ฆ.is this new manager going to add value in those areas and help with your short > medium term headwinds? If not, do you even want to outlast the next RIF? The fact you articulated the above, kinda indicates that deep down, you know the grass may actually be greenerโ€ฆ..
TheColdestColdCall
Executive
3
Enterprise Account Executive
All great points here. I want to be clear too that our organization and product has had great success in analyst space, consistently outlined as a leader in our market and so I use the term lackluster loosely related to how we as a theater, or company, haven't hit plan in those three years. From what I know, most orgs should have around 50% (Best in class) hit quota and those who exceed, pick up the slack of the lower 50%. In our org, 20-30% are hitting quota and in some cases, blowing it out while the rest of the org is missing quota by 10-30% and a large share putting up 30% or less in attainment. In a lot of ways I think it's just bad sales planning and territory management but regardless, that kind of pressure on a CRO is going to have adverse affects.

I'm unsure if this new manager will grow to be a good mentor and partner to my deals, which I sort of need as I solidify my career as an ENT rep. I've made great money and been a consistent provider of revenue, always in the top half and top quartile of performers but just haven't seemed to break quota and in comparison to the broader org, I'm "safe" but nobody is safe right now regardless of leaderboard.

I think on your last point, I DO believe there are greener pastures but I'm hardheaded and not one to run away from discomfort as I believe growth is through challenge/pain/discomfort. Then again, deep down... I think it just may be time for a change.
Sunbunny31
Arsonist
1
Sr Sales Executive ๐Ÿฐ
For me, it was that I finally got tired of great products but bad GTM for most divisions and a roll of the dice if you could stick with a good manager/territory/plan, and have that crapshoot happen every single year, and having that result in some absolutely terrible years financially. It was exhausting.
Rosie
Catalyst
1
Sales Director
When itโ€™s time to leave - you leave.

โ€the easiest person to lie to is ourselvesโ€
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