Should I stay and become a manager or help my friend?

Hey hunters,

This March it's been 3 years since I started working in B2B sales in the IT industry. I've been working for the same company all these years, but it wasn't a good choice because it's a 50-employee company with no solid sales department (the CEO taught me sales, but he did sales himself because he was the founder of the company). So I think I should start with corporate jobs where I could work under a sales manager who knows how to sell(then I would learn it the right way). I'm a little disappointed, but at the time I didn't know what that should look like (I was excited about the prospect of working under a CEO ;)). 


We started as a custom software development company, working on a project model for various technical and non-technical founders from the US and UK. Within 9 months I was promoted from SDR to BDS, and of the team of 3 SDRs, I was the only one left (the rest were fired). I lived with the assumption that I was doing great and that I was somebody in the sales world. After a year in sales, I was responsible for all sales activities (inbound, outbound, account management, upsell) and we moved to a staff augmentation/leasing staff/outsourcing only model. This was difficult for me because the CEO went to work on his product and left me without any guidance. I'm not the drama queen type, so I buckled down to hard work and did the best I could. Now, after these 3 years, I know that I mostly closed referrals, inbound and upsell, so I was not successful in active sales (outbound). 


I'm disappointed with my growth because I'm good at inbound sales and account management but to me, it's weak to not be able to actively acquire clients. My current company is super happy with me and sees me in a management position. I, however, am unhappy with my performance and have even thought about quitting sales. 


At this point, I was approached by a colleague who has the same company(1,5 years on the market, a few clients, not solid processes), but it is still very young. He offered me to join the company for a salary (less than at present) and the possibility of shares within 6 months. There, apart from selling, I would slowly take over the position of CEO. An interesting idea, because developing something with a friend and on our account. However, in my current company(12 years on the market, well established, solid clients), I know that I could become a manager on my way to profit-sharing if I create a good sales department. In both companies there is still a lot to do, I do not have that experience but I approach things proactively, logically and pragmatically. The question is whether I am throwing myself in too deep by wanting to join a colleague's company and should rather focus on specializing in my current company. I am 27 years old, graduated from technical university and in sales I use the fact that I am an engineer who has well-developed soft skills.

🎯 Career Development
9
UserNotFound
Politicker
4
Account Executive
I worked at MSPs for years- I would never. N. E. V. E. R. go to a startup for less money. It’s a cut throat industry and can take years to build up enough base to begin paying as it should. Especially wouldn’t do this with a friend because friendships rarely outlast a business relationship. <br><br>Your current company will likely sponsor you to go to a sales training that focuses on outbound if they see you in management. Have you asked? Build a case and go with details- where you want to go, how long it will be, how much it will cost with hotel + travel, etc included and what the benefit will be for them. CEOs usually know a good investment when they see it.
AntifragileSalesman
Opinionated
2
Business Development Specialist
Thank you so much, it is true. They would love to invest in me because they see that I brought a lot of business value taking sales after our CEO.
TennisandSales
Politicker
3
Head Of Sales
dude you are being WAAAYYYYY to hard on your self!! 

it sounds like you are the MAN at your current company and that you are doing well. 

be proud of that. sounds like you have closed deals, upsold customers and lead a team? 

that is REALLY good experience and if you havnt closed  a deal from cold call to close that is 100% OK! 

the experience you have is valuable. It does not sounds like you should leave your job to me. 

If you need leadership/coaching go find it! 

I am also TERRIFIED of the idea of working with a friend. it just doesnt seem to work out. seems like a step in the wrong direction. 

it doesnt sound like its time for you to leave your role but when you do you should be set up for a solid manager/director role. 

keep going!
AntifragileSalesman
Opinionated
1
Business Development Specialist
Hey Man, I think that you are right a lot of my friends say the same I am too harsh for myself. It is just that I want to be really good, but sales are not so linear as tech (push X and you get Y). When it comes to friends and business, I haven't been practicing that but what you say sounds really terrifying.
Sunbunny31
Politicker
3
Sr Sales Executive 🐰
Closing is closing, regardless of where the lead or opportunity generated.

If I may give a word of advice:   don't go looking for reasons to be down on yourself or your abilities.   Do your best to be appreciative of your own skills and accomplishments.

Regarding the situation, sounds like you stumbled into a career that has turned out to be interesting and in which you've had success.   Not all paths are linear and it sounds as though you've made the most of what you have.   Moving to a role, for less money, to work with a friend and phase into a CEO role sounds exciting but also incredibly risky.   If you think you're unprepared to be a sales rep, why would a CEO role be any different?

RE the lack of formal training and guidance:  there's a lot of sales training material online and in books (search bar in here will give lots of links).   You can do some self-education that way to hone the craft you already have.

Honestly, you sound like you're in a good position and have done a lot with what you have.   
Justatitle
Big Shot
2
Account Executive
Listen, I do not care if the lead source is inbound, outbound, social, referral. Can you close business and are people signing? Outbound has a historically low closing percentage vs inbound not saying it’s impossible but hand raiders are easier to close.
AntifragileSalesman
Opinionated
0
Business Development Specialist
Thanks for the words of encouragement. Yes, through those 3 years I was able to close projects and staff augmentation projects, that is why my company keep me close ;).
AessK
Politicker
2
SDR
While getting good at being a hunter is a badass skill to have, something I've learned is that prospecting AND closing outbound deals = 90%+ timing, luck, and other variables you can't control. No need to be so hard on yourself.

You sound like you're doing great - the grass isn't greener all the time. I'm quickly realizing how much small shit can add up in a startup (operational inefficiencies, lack of training, ect). If you're open to deal to deal with all of these responsibilities + hiring/scaling a startup at a very high failure rate + other things, you do you!
NotCreativeEnough
Big Shot
1
Professional Day Ruiner
If you are unhappy with your performance, I wouldn't recommend another startup. Look for companies with a well established sales org and sales training program. Until you're able to actively go out and hunt for your own prospects, you aren't marketable as a sales person. Anyone can close inbound leads. Being able to go out and hunt your own is where you really get skilled and become and asset to a company. 

If your goal isn't to stay in sales however, your friends company may not be the worst idea. But as a CEO you're still a sales person and still working deals. Just not with customers anymore. at least not once its a well established company. But you're still negotiating with other companies, vendors to get products, etc. 

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