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Leadership path or IC for life?

Struggling with this question, personally.


I have enjoyed being in leadership positions in the past, not in sales but in other aspects in life. I also enjoy being a mentor and imparting knowledge for the benefit of others.


On the other hand, I work with Key Account guys that are in their mid/upper 50s that have been crushing $500k+ on their W2s for well over a decade. And if you were to ask them why they haven't moved to leadership they usually have a litany of reasons.


Thought I'd take the temp of the War Room.


Are you hoping/planning to eventually move into a leadership role (Manager, VP, SVP, CRO, etc) or are you an IC for life?


People already in leadership: Was it worth the switch? Downsides? Would/could you ever go back to being an IC?

🎈 Mentorship
🧢 Sales Management
🚀 Career Goals
21
BigMeech
WR Officer
+11
Coors Light Advocate
My plan is be IC until early 50s, max out the earnings, 401K, etc, then shift into leadership until I retire. 
MMMGood
Celebrated Contributor
+10
Senior Account Executive
Yep...I'm feeling this, presently. 
SaaSbod
Contributor
+3
Sr Sales Account Exec
I don't see a lot of older leaders anymore. This sounds ideal but it isn't what I see in tech. You would also go from working your own schedule to nonstop spreadsheet hell. 
Abydocomist86
Client Manager
Yup, I'm staying put until I max out as well. Who needs that extra stress. 
Coffeesforclosers
Notable Contributor
+11
Director Sales and Market Development
Got into leadership at 30, miss IC so much. stay there forever lol
MMMGood
Celebrated Contributor
+10
Senior Account Executive
Haha...any reason in particular for you to give that advice? 
Coffeesforclosers
Notable Contributor
+11
Director Sales and Market Development
work life balance as IC is way better, you have kids you have freedom as IC that you dont in mgmt
Show 5 more replies
detectivegibbles
Politicker
+8
Territory Rep
I'd have to assume a lot of career salespeople struggle with. I'm "young" (32), but it's something that my bosses have brought up to me a few times. 

I think the bigger question is...What feels more fulfilling to you when you close your eyes at night? 

Do you find joy and happiness in seeing people you lead grow? Or, and this is totally fine as well, making $XXX,XXX that you may not make in a leadership position? 

I'd guess that most IC's that are making those large figures are on cruise control; book of biz, not having to cold prospect, etc. 

That would be very hard to walk away from in my eyes, UNLESS there is a desire to help others grow. 

Great question, thanks for sharing!
MMMGood
Celebrated Contributor
+10
Senior Account Executive
And thank you for being so thoughtful in your response. I'd say there is a desire to help others...but I'm not convinced that it's something that needs to be realized in my professional career vs other areas in my life where I could be a mentor: Boy Scouts, church, within my family, volunteer work, etc. 

I'm only in my late 30s so I feel like I still have time to mull this over. But the reflections of others is a great help. 
goose
Politicker
+10
Sales Executive
Manage people that don't hit their number and you'll long for the days of late starts, long lunches and late afternoon tee times with clients.  

Participate on a team of savages that crush the number and watch VP drive away in a Porsche and you'll salivate for the corner office.

The grass is always greener...
MMMGood
Celebrated Contributor
+10
Senior Account Executive
Have you had a leadership role that prompts both perspectives? Or just your take on both? 
goose
Politicker
+10
Sales Executive
I've held both.  They both have their benefits.
DS
DSC
Old School Bravo
CEO
I was an IC, then VP, then SVP, then CRO at 4 early stage companies and am now Founder/CEO of my own revenue growth consulting firm.  My advice is to explore leadership roles but to always (always!) continue to personally prospect and sell to both help your team and to keep your network and sales skills fresh.  When I kicked out on my own it took two weeks to be fully booked with clients because I made the effort to stay connected during my corporate leadership runs.  Also, I believe in Servant Leadership.  Your only goal as a leader is to make those on your team successful.  If you adopt this approach and put ego aside leadership roles can be awesome.  As for retirement, what the hell is that?  I'm structuring my biz so that I can run it until I'm 75 if I want.  Golf is too boring. 
MMMGood
Celebrated Contributor
+10
Senior Account Executive
Yea, I'm not sure I'll ever retire! Haha. Thanks for sharing your thoughts and experience!
funcoupons
WR Officer
+11
Kahluapons
I'd be open to a leadership position down the line. I like being an IC, but don't know if I see myself doing it for the next ten years. 
MMMGood
Celebrated Contributor
+10
Senior Account Executive
See I said the same thing...then got referred to interview for a VP role (didn't end up being a good fit for me, so I backed out) which made my start questioning it MUCH sooner than I thought I ever would. 
funcoupons
WR Officer
+11
Kahluapons
Questioning is fine - always good to keep an open mind. Switching from IC to management definitely calls for the right fit. You need to love the proposition, not just think it's ok. Keep being picky. You'll know when it's time to switch when an exciting opp comes up.
Show 2 more replies
Salespreuner
Big Shot
+11
Regional Sales Director
leadership by or before 35 (in it already) & lead a group by 45 and then preach the path to many

best ? This works through immense efforts in IC which I did :)!

so IC for 10 years is a good way
MMMGood
Celebrated Contributor
+10
Senior Account Executive
Any suggestion or recommendations? 
Salespreuner
Big Shot
+11
Regional Sales Director
Territory incharge in IC to start. Then go to zones with 1-2 member teams and then scale up
Chep
WR Officer
+10
Business Development Team Lead
Just moved into a leadership role and it gave me great pride having my teammates gas me up about it. Really depends on your company. I was nervous for the switch, but having everyone on my team support me made me very grateful
EQSales
Good Citizen
+1
VP of Sales
from someone who has been in leadership for about 7 years and got there relatively fast in my still early career, here's my 2 cents:

1- how successful you were as an IC plays a huge part in this discussion.  If you finally made it to the sweet spot in enterprise sales (at least in my industry, SW sales) and have not had a 200%+ year I advise against a fast move to leadership.  Either have 1-2 bonkers W2 years or spend time cultivating a solid 4-6 year track record of overachievement.  leadership will always be there for those who want it and perform.  use the time to get better and pad your future, the next job will need it

2- how are you entering leadership has significant impact on your earnings and path- IE inside sales vs enterprise.  enterprise is much higher earning, equity and puts you on a vaulted earnings path

3- the most important of all- if you do not GENUINELY love helping other people, leadership will not be for you.  it is a grind, first line enterprise leadership might be the hardest job in sales.  you have to deal with shit you never imagined.  the path to failure is infinitely larger than as an IC, you won't make as much as an IC if you were a true A player and you won't get near as much training on leadership as you did on being a rep.  BUT if you really love seeing other's grow and develop, leadership for me personally, has been far more fulfilling than any of the commission checks I received as an AE

also add- you can always go back to IC, and as a leader you will learn to read the matrix code with all the deal flow you will see.  makes for a very skilled seller
MMMGood
Celebrated Contributor
+10
Senior Account Executive
Thank you for that perspective and insight. Much appreciated. 
Lumbergh
Politicker
+3
Sr Account Exec
You sound like a great leader.  There are far too few of you [at least in software] these days.  Keep fighting the good fight
EQSales
Good Citizen
+1
VP of Sales
thank you! just love seeing people develop and achieve things they never thought possible, because i was given the same chance.  super rewarding but i wouldnt survive if this didnt fill my cup.  its really fucking hard work
saygrace
Valued Contributor
+5
Sales Executive
IC + side hustles until I outgrow it.
MMMGood
Celebrated Contributor
+10
Senior Account Executive
This is the current MO. Eventually, my bandwidth for side hustles is going to lessen. So I'm trying to determine when that sweet spot for making the jump to leadership. 
SlanginHCSaaS
Opinionated
+1
Regional Sales Director
I'm on the verge of transitioning from IC to leadership. I'm about to turn 45. I think for some it's the right move, but ultimately it comes down to whether or not you think it's the right fit for your personality and goals. The grind of IC can get old after a while. I'm eager to move to a position where I can mentor and work with sales reps, I like the idea of a higher base, I like the path of a Director>VP>C Suite and all that comes with it, etc
MMMGood
Celebrated Contributor
+10
Senior Account Executive
Would you mind characterizing “all that comes with it” a little? Wanting to understand the upsides. 
SlanginHCSaaS
Opinionated
+1
Regional Sales Director
The higher base is huge for me. I have a significantly higher base now than I did in my last IC job, and my stress level is way more manageable now. I can only imagine this will continue to improve as I move to leadership and that base grows. 

This might be just me, but another thing that "comes with it" is more input on how shit gets run. I was always the IC who would comment to colleagues at lunch about how stupid some of the directives were that were coming down from above. Now I'll have a voice in these leadership meetings and get to provide my input on what I think sales should be doing. The generation of "make 200 dials a day" is slowly slogging towards retirement. It's on us (GenX, Millennials, GenZ) to shake up sales leadership moving forward and bring a more modern approach to sales. I really want to be a part of that.

Finally, being a "VP" or "CRO" just slaps. 
Show 5 more replies
CJE
Politicker
+6
Account Executive
Some days leadership, some days IC
MMMGood
Celebrated Contributor
+10
Senior Account Executive
Do you have a plan to move into leadership soon? If so, why?
Allisce
Opinionated
+2
Account Executive
I struggle with this because I have held leadership positions in the past but I love the control of being an IC. Also, so many of my coworkers are idiots and the idea of depending on them to hit my number is insane. I was asked to apply to lead a team this year and pass don it because it wasn't my specialty, I'm focused on new business while this was client sales, and I'm so glad I passed. Basically all I want is a better base

devopsdude
Opinionated
+1
Account Executive
IC for life. I was a manager of a team of 12 for about a year and hated it. 
braintank
Politicker
+6
Enterprise Account Executive
I was a top IC and was offered a promotion to leadership several years ago. Tested the waters and absolutely hated it. Spent most of my time in BS internal meetings or dealing with petty squabbles among the team (e.g. why does X have a desk closer to the window when I've worked here longer than them?) It made me hate my job and dread coming to work. Moved back into an IC role at another company within a year.
MMMGood
Celebrated Contributor
+10
Senior Account Executive
The grass is always greener, right? 
braintank
Politicker
+6
Enterprise Account Executive
In retrospect I'm happy I did it becuase now I KNOW I want to be an IC for life.
Show 1 more replies
billybillerson
Old School Bravo
Application Sales Manager
I've been both. IC at companies like Adobe and Oracle. VP of Sales at a couple of early and later stage startups. Maybe it was the shakiness of startup life, but I felt like I was working for other people more as a manager. If you go that route, make sure you have a leader who you see as a mentor and/or have a trusting partnership. I've had both types of upper level management that I have worked with and it really affected my work-life balance when having a good versus a bad team around you.
MMMGood
Celebrated Contributor
+10
Senior Account Executive
Having a good mentor is absolutely great advice and something I always try to maintain, both in the company I work for and outside. Thanks for sharing. 
CaneWolf
Politicker
+12
Call me what you want, just sign the damn contract
What kind of bullshit are you looking to endure? I personally enjoy coaching and helping others grow but I do NOT see there being a ton of joy in the management world. I'd rather keep the freedom and live the lifestyle I want.
Dr.Sales
Executive
Google “Peter principle sales” great podcast.
MMMGood
Celebrated Contributor
+10
Senior Account Executive
Great...I'll check it out. Thank you. 
JJASBE
Catalyst
+6
Sr. AE
I'm not married to IC or leadership.  It depends on the company for me.  Some orgs I'd gladly be an IC, because your voice is heard and your ideas adopted, without the meetings about meetings and spreadsheets to validate spreadsheets.  In other orgs, being a leader is actually the best-paying role, and you get to actually spend 50+% of your time coaching and developing your people.  
CoastLife
Good Citizen
Large Enterprise Sales
IC all the way! Management is such a different beast. 
I was a sales leader for a while but much prefer the freedom that comes from being an IC. And just because you aren't in a management role doesn't mean you can't be a leader/mentor. 
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