EsteComoEs

Head of Sales

How to get the CEO/Founder off of my ass as the Head of Sales

This question can be a bit universal as well as it can also apply to VPs dealing with C-Suite, rep dealing with an overbearing manager, etc. But if anyone has specific guidance with experience as a sales leader dealing with a Founder, that would be incredibly helpful.

I let our CEO know that I've he's brought more conflict to me in the short 60 or so days that I've been here, than I have from any other manager in my entire career.

The training and official direction is very lacking. I have a 30-60-90 (3 slides only) that has been some sort of direction, but any other direction is when I'm getting beat up in a 1:1 being told I'm not doing enough and I'm not communicating enough on my efforts.

Any thoughts or guidance would be VERY appreciated.

🧢 Sales Management

☁️ Software Tech

16 comments

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Kosta_Konfucius

Politicker

Sales Rep

I am just a simple individual contributor, but when I started a role where I was just getting asked in every meeting "why am I not setting x amount of meeting?" When I didn't even know I need to set that amount. I had our next 1:1 going through our 30-60-90, seeing where the disconnect was.

We discovered areas I thought I exceeded, she thought I missed. And also changing it to goals that were her and our leaderships expectation since the roadmap was generic.

Not sure how relevant this story is, but maybe it can be useful to go through the 30-60-90 again and talk ideal communication style.

SoccerandSales

Big Shot

Account Executive

Having them review their expectations of you and how they want you to go about things is going to be crucial. Without that mutual understanding, it is more likely both sides will continue to be frustrated

CuriousFox

WR Officer

🦊

Soccer yes 🔥

Sunbunny31

Politicker

Sr Sales Executive 🐰

This is such a good perspective. Making sure that expectations are clear and understood and that they mean the same thing to each of you is going to be important. You and soccer both have it right.

EsteComoEs

Personal Narrative

Head of Sales

Thank you this is helpful.

SADNESSLieutenant

Politicker

Officer of ♥️

I once reported to a ceo. I have a whole saga on that. I would flip the question on them. What are they doing to empower you to do enough?

Im sure they arent providing clear direction or insight.

You might just have to leave. A bad ceo is like an overgrown baby with poop smashed on its face and proud of it

bja009

Politicker

Enterprise AE

I came here to say basically this, with a side helping of Kosta_Konfucius' advice.

If you have the type of CEO/founder who is constantly reminding you who the boss is, you're better off just bailing. They will never support you and will use you as a scapegoat. I know because I *just* left that environment this week (and got a 50% base raise too hahahahaha)

But if you think this CEO/founder is just a poor communicator, well, you're in sales so communicate for the both of you. Clarify expectations, set clear goals and agendas, make sure the rest of the leadership team also sees and understands the plan so that it's reiterated from other channels to the CEO, not just from you. You'll have to manage up, but the rest of the job might be worth the effort.

hh456

Celebrated Contributor

sales

Hey,

I’m c-suite (I sell insurance over the phone) and my ceo is very involved too. There’s 3 things going on that you’re gonna have to put up with and how to shorten this phase.

1 - he doesn’t trust you. You’re new, you have rope, if he is unhappy you’re gonna hang on it. He’s clearly communicating his style to you, so do it. Bcc him on every email, every note, send him a daily report, just bombard him with communication. He will ask you to tone it down after he sees you’ve got the message. Also, work more. I hate it cause I’m an advocate of less work but it sounds like you joined an early phase company. If you want less work, join IBM. Being vp of sales at a start up is 7 days a week, 12-16 hours a day. It is totally wrong to live that life if you don’t enjoy it or want it, but you signed up for it even if you didn’t realize it.

2 - you may have not produced yet (idk) and don’t know what direction he’s seeking. Idk what kind of sales you’re in but does he expect a sale every 30 days? Does he expect 15% lift? Ask for goals, make him clearly articulate so you can succeed.

3 - he was the first salesman. Never forget that. Whatever he did he paid for you to be there. Don’t expect CEO’s to become distant in start ups. He got to a point where he can hire someone to sell, a professional, so he can focus on the product and raising money. That is always in his head. The only way to reduce his anxiety to a QBR is to succeed and out perform him.

There wasn’t too much context about your organization but I hope that helps. It sounds to me like you’re floundering and the best way to bridge the gap is to communicate, have him articulate his goals for you & put in the work to exceed them. You may or may not be able to do that, but at least you won’t get canned for lack of effort.

Pachacuti

Politicker

They call me Daddy, Sales Daddy

So the CEO/Founder is micro managing you as the Head of Sales? Not a big shocker.

He's probably been the head of sales of his company at some point prior to you coming on board and letting go is difficult for him. Its going to be a process and will take time to gain his trust. Just because he hired you doesn't mean he trusts you.

You ought to ask for a regular cadence meeting with him so you can focus on your job and build communications with him.

ThatNewAE

Big Shot

Account Executive - Mid enterprise

When a company is on the verge of not doing great, the CEOs might micro manage sales heads. I have read a lot about this, seen this in my organizations as well. I know anything you'd do right now might either make your CEO distrust you or make him micro manage you more.

Maybe just let it pass by, not say or do too much in the beginning.

ChumpChange

Politicker

Channel Manager

You're going to need a "Come to Jesus" calibration session.Anytime you directly report to someone, always ask the following:

What are the duties that you're now responsible for?

What are the resources at your disposal?

What is the timeline or commitment window?

What are your expectations?

EVERY SINGLE TIME... no matter what. Also, make sure to write them down as they state them because this is going to be used as leverage in the future when they ask you to do something outside of the answers that were given. It's not if they do this but when they do.

antiASKHOLE

Tycoon

Bravado's Resident Asshole

Get your numbers up

Killebrew

Valued Contributor

Tough to say without knowing him and what exactly he does. There's a lot of different ways to be overbearing and the issue is a lot of times guys are just baked that way and if you don't like it you can move along.

My solve was to make sure I took copious notes and made sure he knew I was the type of guy to take copious notes and made a habit of entering those notes in the CRM right after our meeting.

I ended every meeting with "So I'm clear before I enter this into CRM, we're agreeing that the plan of action is [whatever dumb shit he wanted me to do]" That way if he came back on me I'd have a confirmation that we agreed on this strategy.

Then, he'd tell me I should have told him he was wrong (he was not a guy who would tolerate being told he was wrong) but again, some people are just assholes.

Hakuna_matata

Fire Starter

Co-Founder

Show results more than ever before to gain more autonomy!

BlueJays2591

Politicker

Federal Business Dev Director

You're there to lead the sales efforts to help the company reach the goals set by the CEO. The CEO needs to trust the people they hired to do the job. I would have a conversation with them to discuss the concerns before it gets too bad.

kiwicloser

Member

VP of Sales

A VP of Sales or Head of Sales is not a magic wand. They should give you clear expectations of what they expect then give you the autonomy to achieve those goals.

The problem with a lot of start-ups is that the founder is usually a tech bro or introvert weird pragmatic engineer type. They are often terrible communicators and hire a head of sales to fill in the void parts of their own personality.

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EsteComoEs

How to get the CEO/Founder off of my ass as the Head of Sales

16 comments

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