MMMGood

Senior Account Executive

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?

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60 comments

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CoorsKing

WR Officer

Retired King of the Coors Knights

My plan is be IC until early 50s, max out the earnings, 401K, etc, then shift into leadership until I retire.

MMMGood

Celebrated Contributor

Senior Account Executive

Yep...I'm feeling this, presently.

SaaSbod

Contributor

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

Director Sales and Market Development

Got into leadership at 30, miss IC so much. stay there forever lol

MMMGood

Celebrated Contributor

Senior Account Executive

Haha...any reason in particular for you to give that advice?

Coffeesforclosers

Notable Contributor

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

MMMGood

Celebrated Contributor

Senior Account Executive

I agree...and this is something my wife and I talked about very recently. IC you have your quota and your own little island. Run your franchise, hit your number, reap the rewards.

Leadership has it's benefits as well for sure...but you get tied up in A LOT of other dimensions within the org that take up a lot of time.

Coffeesforclosers

Notable Contributor

Director Sales and Market Development

Spot on. And management still has a number but it's on my island reps that only care about their island lolololol. Plus all the admin and executive leadership bs.

MMMGood

Celebrated Contributor

Senior Account Executive

Exactly. I'm not sure I want that for my life (read "family life") right now. Maybe when my kids are grown and out of the house. I just really appreciate the ability to keep my schedule flexible, within my own "franchise's" needs.

Coffeesforclosers

Notable Contributor

Director Sales and Market Development

F yeah man. It was great the first 5 years of my kids life

SaaSbod

Contributor

Sr Sales Account Exec

Agreed - Also you give up the driver's seat. You are no longer in control of the effort or revenue. The skill set isn't exactly the same either, just because you sell well does not mean you have leadership skills.

detectivegibbles

Politicker

Sales Director

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

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

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

Senior Account Executive

Have you had a leadership role that prompts both perspectives? Or just your take on both?

goose

Politicker

Sales Executive

I've held both. They both have their benefits.

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

Senior Account Executive

Yea, I'm not sure I'll ever retire! Haha. Thanks for sharing your thoughts and experience!

funcoupons

WR Officer

👑

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

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

👑

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.

MMMGood

Celebrated Contributor

Senior Account Executive

Great perspective. Thanks for your thoughts.

funcoupons

WR Officer

👑

Anytime!

Salespreuner

Big Shot

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

Senior Account Executive

Any suggestion or recommendations?

Salespreuner

Big Shot

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

Bitcoin Adoption Specialist

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

Opinionated

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

Senior Account Executive

Thank you for that perspective and insight. Much appreciated.

Lumbergh

Politicker

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

Opinionated

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

Sales Executive

IC + side hustles until I outgrow it.

MMMGood

Celebrated Contributor

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

Executive

Enterprise Sales Executive

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

Senior Account Executive

Would you mind characterizing “all that comes with it” a little? Wanting to understand the upsides.

SlanginHCSaaS

Executive

Enterprise Sales Executive

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.

MMMGood

Celebrated Contributor

Senior Account Executive

Solid perspective, all around. Thank you very much for sharing!

goose

Politicker

Sales Executive

The average stay for a VP Sales is 18 months. Miss the number and the investors / board won't put you on plan...

That slaps in a different way.

MMMGood

Celebrated Contributor

Senior Account Executive

My last RVP/boss was with the company 8 years and blew out his number every year. Told me after he left the company, when we were talking this same subject, that he averaged $500k/year.

So...when you ARE performing...slap back.

goose

Politicker

Sales Executive

That's great to hear

SlanginHCSaaS

Executive

Enterprise Sales Executive

I've never been on a PIP, I don't plan on starting now. The move towards leadership is just another challenge, and I'm eager to face it.

CJE

Politicker

Account Executive

Some days leadership, some days IC

MMMGood

Celebrated Contributor

Senior Account Executive

Do you have a plan to move into leadership soon? If so, why?

Allisce

Tycoon

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

Account Executive

IC for life. I was a manager of a team of 12 for about a year and hated it.

braintank

Politicker

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

Senior Account Executive

The grass is always greener, right?

braintank

Politicker

Enterprise Account Executive

In retrospect I'm happy I did it becuase now I KNOW I want to be an IC for life.

MMMGood

Celebrated Contributor

Senior Account Executive

Yea..a few others have shared that "option" to always be able to go back to IC. Sometimes the only way to know is to try.

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

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

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

Senior Account Executive

Great...I'll check it out. Thank you.

Blackwargreymon

Politicker

MDR

Got into leadership at 30, miss IC so much. stay there forever

JJASBE

Catalyst

Director, Solutions Sales

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.

MR.StretchISR

Politicker

ISR

The latter for sure. As much as I love reading that stuff I find most keyboard warriors have nothing to gain from piling on

YinYang

Contributor

VP of Sales

Ask yourself these three questions as you're considering a leadership career:
1) are you willing to fully give up control of your quota?
2) are you comfortable with the knowledge that there's a chance you'll earn less than your top performer in commission?
3) does the prospect of being both a councillor & coach appeal to you?

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MMMGood

Leadership path or IC for life?

60 comments

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