Savages,
Long post warning but should be useful
I have seen a variation of this question posted probably 23957032975 times in the War Room over the past 6 months or so. Considering I just went through this decision over the last 2 weeks I wanted to share a quick framework I used to make this choice so others in the same spot have a starting point.
Context first - I have been at my current company for over 6 years, I have learned and grown a SHIT LOAD while here. I actually wasn't even looking for a new role but when my old head of sales (and best sales leader I have ever worked for) reached out, my ears perked up. This leads me to #1 in no particular order:
1) Understand who your next leader will be: Do you connect with them? Do you trust them and have prior experience or is this an entirely new leader?
For me, this part was a no brainer. I have experience working with her, I trust her and she knows how to push me. If you aren't as fortunate and it's a new experience ask questions about ongoing training for management, how they structure their team, training and development tools already in place. Gain an understanding of how they operate and who they are.
I cant understate how important it is to click with your leader. You can fail with a bad one, you can succeed without an average one, but you will kick ass and break records with a great one. Don't discount that when moving from a known to an unknown.
2) Does this company have legs? If they are public, hows the stock performing recently? If private - how big are they (head count, ARR, size of sales team, current customer base etc) What is their revenue growth YoY. What series are they in and what are plans for future fundraising? Is there solid product market fit? There are so many failing startups throwing red flags all over the place that with some decent discovery you can identify and avoid.
The company I am moving to is under 70 employees but has hit some important revenue benchmarks, is already profitable after 3 years (SaaS business), They grew through COVID and 7xed revenue YoY and is projected to continue on that pace for the next 3-5 years. Im not counting chickens before they hatch but thats a sound sustainable business. They dont need funding from Series B to continue growing putting them in a powerful position with VCs.
3) Career Growth Opportunity - are you making a lateral move or taking a step up?
Pretty self explanatory, In my situation, I am going from a management role into a director capacity, No brainer.
4) Current AE performance - What is the median rep quota attainment? What are top performers doing and what are bottom performers doing? This is a pretty good indicator if you are joining a shit show or not.
Current sales team I will be taking over is small but they are averaging 120% to their number with top AE's doing 250%+
5) Compensation - last but certainly not least, this switch better be worth it, short term and long term
I am taking a 33% base and OTE increase here along with significant equity with a path to more. This makes the switch a no brainer for me.
If you made it this far, thank you for joining, I appreciate you.
I know I have missed important shit so others please feel free to chime in on how they evaluate a job change.
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