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BitcoinAddict

AE

Opinionated
Valued Contributor
Member
+6

Salespeople who manage to stay at companies for 3+ years, how?

It seems like in our industry, so many Enterprise AEs and even Commercial AEs switch jobs every year or every 2 years. I've ideally wanted to find a company where I can spend the next 5 years of my life and grow. Had my 2 year anniversary a couple months ago at my current company and already I feel like it is a struggle to get up:


  • So many of the leaders that help build it have left
  • So many AEs I learned from and was close with left
  • Management has become toxic now
  • New hires are friends of management from other companies so they are taken care of
  • Nepotism has practically taken over


It's almost unrecognizable from when I first joined. What's weird is that this has been my longest tenure but I am early in my career (it's my second ever SaaS sales job), last company got so bad after year 1 that everyone left in droves.


For those of you who have managed to find a place where you can stick it out for 3+ years and ideally even 5, how? What should I be asking in the interview process to find my 5 year stay?



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37 comments

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SaaSam
Politicker
11
Account Executive
Truth is, you'll never find out during an interview if the company you're thinking about joining will be "the one" for the same reasons that you're unhappy after 2 years at your current company. Things change over time and not always in a good way.

Plus, every interviewer says their company is the best place to work and they have an amazing culture so even if it sucked working there, they aren't going to tell you. 

Your best bet is to find current and past employees of a company you're considering and ask them what it's like. Especially the ones that don't work there anymore, ask them why they left, if they'd ever go back. 

Ex employees are the most honest about what it's like to work at a company. They have nothing to lose by telling the truth. Personally I don't make my decision based on the positive "reviews" I make it based on the negative ones. It's pretty easy to tell if someone is being genuine about the cons of working somewhere or if they were just terrible employees that finally got the boot.
SaaSsy
Politicker
7
AE
I love your rec of finding ex employees, I will never NOT do this again - so important to hear about all the BS up front and know if the offer is still worth it or not. There are cons everywhere, it's knowing that you can work with those or not.
SaaSam
Politicker
1
Account Executive
Definitely, nowhere is perfect. I love where I'm at and there are still a few things I would like to change.

At the end of the day ex-employees, disgruntled or not, will be the most upfront about the ugly side of things.
BitcoinAddict
Opinionated
5
AE
Plus companies fluff their reviews on Glassdoor and often have bad reviews easily taken down.
SaaSam
Politicker
0
Account Executive
Yup, that's my approach on anything. I make my assumptions based on the bad reviews.
SaaStruthATX
Valued Contributor
0
Senior Enterprise Account Exec
That's the truth! the worst company I have worked for was large one with a great glassdoor rating.
Sunbunny31
Politicker
8
Sr Sales Executive 🐰
Luck plays a huge role here.    Landing a position and have all the change over time be positive is a roll of the dice for a large part.

But - the effect of upper management cannot be overstated.   Is your CEO a visionary, inspirational, or toxic?    If s/he is anything other than a good leader, the entire org is going to be a challenge.   Look at sales leadership.  Same thing.   It all rolls downhill, and there's only so much your immediate manager can do to make the situation workable.    If you're not starting in a good place, it's unlikely to get better.
sleepingjaguar
Opinionated
3
CSM, Emerging Markets
100% this. Leadership is everything and as most have already said it’s nearly impossible to identify if the company is truly who they say they are in the interview process. Good luck BitcoinAddict!
voila
Valued Contributor
0
AE
This is some sage wisdom. Yuuup. 
TennisandSales
Politicker
4
Head Of Sales
SAME! 

Longest Ive been at a company in Saas is 2 years....and it felt like a lifetime haha. 

My friends who have been at companies for 5+ years, have ALL endured an INSANE amount of bull shit and have just somehow been able to push through. 

Is THAT the key??? be ok with bull shit????
jackodiamonds
Opinionated
2
Account Executive
Yes
Pachacuti
Politicker
4
They call me Daddy, Sales Daddy
I have wanted 5-8+ years out of nearly every job but have yet to be somewhere longer than 4. Usually I become disillusioned or i get a strong compelling offer. Have been laid off too which has taught me to always look out for myself first.

Also to move up you often have to move out.

Most sales people are not content with the status quo which is why we are are constantly looking and ready to move on. Do what is best for you and don’t apologize for it.
SalesBeast
Politicker
4
Sales Director
Don’t expect shit and you won’t be disappointed is also good advice. Expect to make a check and that’s it.
E_Money
Big Shot
3
💰
Yeah I am still looking for a nice place to hang my hat longer term. Nothing longer than 2 years yet though. 
SalesBeast
Politicker
1
Sales Director
Nepotism HUGE these days. It blows.
Few options.
-put on knee pads and join the crew and nepotism.
-just steer clear of everything and everyone don’t be rude but get the job done and be good at it.
-don’t be a pile of shit that makes excuses. Own your actions. Don’t call in sick a bunch. Be transparent and just straight shooter.
I’ve been at 2 companies very long times 3+yr, 7.5yr
SADNESSLieutenant
Politicker
1
Officer of ♥️
culture is built top-down. for example @ captivate IQ the three cofounders share the CEO title, no one person is running the ship and they all have a 33% stake in the role. They are young, and promote culture top down. You have to find a company that promotes culture not as a second thought, but as the core aspect of the company, that they don't bow down to VC or Traditional Boomer Nepotist bullshit because their product and leadership is more progressive than that. in the end these are the companies that will do better anyways because they will have access to all the best new talent regardless of background
mitch_n_murray
Valued Contributor
1
Closer
I just passed 3 years with my current company. However our sales manager just quit and I have concerns about them hiring a micromanager. Already changed my LinkedIn profile to show recruiters that I am open to opportunities. 
NotCreativeEnough
Big Shot
1
Professional Day Ruiner
find a company who's product you truly believe in and is truly an industry leader. Ever company says they are, but as we all know, they aren't all leaders. - this is easily the biggest key

culture is huge. if you don't like the culture, you won't want to stick around. Make friends with coworkers, go to happy hours, go to team building events, it may feel dumb at the time but long term it will build lasting relationships with your colleagues which will benefit you in the long run. 

Don't always focus on the comp. you can always find someone that will pay you more. that doesn't mean you'll be happier. 

have a good work life balance. a lot of times job hopping is a sign of getting burnt out. Enjoy your personal life and don't let it revolve around work. 

Just a few things I've learned to be happy at a company long term. 
DenverMike
Executive
1
Strategic Account Executive
Been with my current company for 9 years 11 months. My advice, find a smaller company (mine was ~250 people when I joined) and grow with them. If you're good at your job you'll move up the chain much faster than a large company and you can help form the company culture and the people around you. 
Not_2_Salezy
Member
1
Program Manager
My 4 year anniversary with the same company is coming up. This is my 10th year in sales and the longest I've been at any job. Staying power is due to a combination of money / freedom / recognition and the recurring book of business that took me 2 years to build. It wasn't easy. I submitted a formal resignation over a year ago before my manager and the CEO had a come to jesus moment and gave me everything I wanted in order to stay. You'll never be able to gauge any of that during interviews.  Find a reason or two to be excited about the gig and don't have any other expectations other than meeting your immediate financial needs. Make yourself irreplaceable and you can negotiate your way through the bullshit over time.  Every company is dysfunctional. There will always be bullshit.
SaaSguy
Tycoon
0
Account Executive
Im coming up on a year and a half and could see myself at my current gig longer. Sometimes it's just luck of the draw, unless you have a friend at the company who can really break down the inner workings of a sales organization its hard to know the reality of the situation. 

Frankly, there is a lot of benefits of hopping every two years as well. 
Justatitle
Big Shot
0
Account Executive
Typically the model is stick at a company for 18-24 months and then in order to get a pay bump along with a nicer title you need to change companies as your current company probably won't be able to match the new offer you receive. Unless you are hitting 200% of quota and easily at that it makes financial sense to move around to get the most money possible
Jbeans
Opinionated
0
Director of Sales
I like to know about the environment, the vibe. Expectations of quota. Ramp up time to hit quota. How they communicate changes  with comp. but .. they can make things look reeeeally good in this phase. Don’t be sold a dream either. Some people stay bc they have better growth plans or opportunities for advancement than others - or what’s important to me might not be to you? So if there are changes - you have to make decisions as those changes come. I’m one of the last standing OG reps where I am too, but I like to see the growth and as long as we are moving forward and it works for me? I’ll stay. :) 
sleepingjaguar
Opinionated
0
CSM, Emerging Markets
Something I always keep in mind is that if you stay at a company longer than 2 years your losing money unless comp and accelerators are 🔥 this from somebody at a 💩 startup desperately trying to escape after 3+ years 🤡
FinanceEngineer
Politicker
0
Sr Director, sales and partnerships
You keep hitting targets and negotiate them to not move too much. It’s all about setting expectations that are feasible.
champchamp
Arsonist
0
Certified Savage
secks
Executive
0
Account Executive
That sucks. I'm sorry. At least you'll always have Bitcoin? 
MemeStonks
OG Sales Savage
0
Enterprise Account Executive
I’ve learned over the years to not think about how long you want/need to stay at a company. Keep crushing your job, see if your efforts are reciprocated in title/salary/etc, and if not start looking for what you want. Loyalty is fickle, especially when a company can sh*tcan you at any moment…culture goes out the window in those moments.
SalesMama
Executive
0
Senior Account Executive
I think a key to dig into is internal mobility (with specific examples of people making the moves promised). My company has a lot of sales reps between 3-8 years of tenure, but none have been in the same role or selling to the same customer segment for the entire duration of their tenure at the company.
Andrez20
0
South Central Industial Specialist
I’m about to make 9 years at my company. Initially when I had my first review years ago I was also interviewing with 3 other companies. My process was to read into the interviewer and the managers to see if they were truly happy doing what they were doing. Seeing their energy in trying to get you into the company tends to shine, but their experiences and excitement shows more. I saw that my manager had been there for 20+ years, and all of the other managers were under 10 and 5. Speaking with current team members also had some enlightenment on the job. I saw that the commitment and teamwork atmosphere was consistent. That truly sold me compared to the other jobs. 
cautiouslyoptimistic
0
Senior Director of Sales
I’ve been at my company for 7 years - For me it’s all about my direct manager. Only twice I worked for someone I didn’t mesh with and I looked for other opportunities under other sales leaders in the org to move to. It’s worked out really well that way.

Working for a company who gives out raises often (to high performers) is also important and a question you can ask in an interview.
GDO
Politicker
0
BDM
You can screen as much as you want. Luck is hugely involved with this. You can’t forecast what companies/colleagues/customers/market will do the next 5y
saaskicker
Celebrated Contributor
0
Enterprise AE
In my experience, the ones that stick around the longest just stay in their lane. They don't get distracted by the change, just there to sell and collect a check. -- or find a larger company that has multiple products to sell and switch between teams when you feel you've hit the ceiling or burnt out. 
rumshootingtrombone
0
Growth
I stayed because we had just been acquired and there was a huge incentive for the acquiring company to sell our product so the extra commission was great, but as soon as that incentive was over, I was out the door. I had no desire to work for one of the big tech firms. I felt like I was selling internally more than I was actually closing new deals. 

As others have said - find ex employees and talk to them but take their words with a grain of salt since they are an ex employee after all. 
htaylor0306
0
Business Coordinator
I think if you find a position where all your needs are met and you enjoy what you are talking about it’s possible to stay 5 years.
securethesandbag
Old School Bravo
0
SDR | Gaming, iGaming, Sportsbooks
i was a bartender before i got my first job in tech and killed it as an sdr immediately until i got promoted to ae.. the brand i built is strong af but much of that has to do with “not knowing anything about tech life” so i have a pass to act out of pocket sometimes.

the reason i’ve stayed despite TAM depletion is because i can’t imagine a scenario where i’d have the same cushion due to my performance as an sdr and not coming from a tech background.

still feel like an imposter sometimes so i low key feel stuck in where i’m at. i’d be nervous to take on a new role and get looked at sideways because of who i am, how i talk & what i look like.

part of it is loyalty, too. they brought me in as the first pandemic hire & gave me stability for the first time in my life; not just my adult life.

i think about leaving all the time tbh do the TAM issue, but i don’t see myself making the move unless something comes along with a great product, a couple warm hitlist accounts, better pay & some mentorship.

since that’s unlikely for someone with my XP, i’ll think i’ll be here another year to make it 3.

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