ConwayStern

AE

how to manage up?

maybe not the right phrase but nonetheless i'm a little stuck.

at a seed stage startup right now, close with the founder and working as his head of sales.

there's a ton more info i could share but i think the pertinent thing is more generally how to deal with mismatched expectations. specifically, he's huge on efficiency and using AI to automate as much of our process as possible.

that's fine in a lot of areas but for example, i wrote out a sales process and stage/exit criteria matrix this weekend, based on our experience over the last couple of months.

data validation is taking a backseat to scaling (another topic entirely) so the inputs were largely based on qualitative reviews of our pipeline, closed deals, and other variables across a variety of data sources.

his response was positive, but also caveated that he thinks a "doc like this shouldnt take more than 5 minutes with GPT."

maybe i just complained here more than explained but would love to hear input from the savages here.

💻 Automation

📢 Communication

😤 Conflict Resolution

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Sunbunny31

Politicker

5

Sr Sales Executive 🐰

Sounds like a commendable effort, and I’m sorry it wasn’t appreciated. ChatGPT wouldn’t have given you a relevant or current response anyway - unless you have your own dedicated ML, GPT is by no means going to give you what you were able to produce. Use of AI is encouraged where I work as well, but fortunately the limitations of GPT are well known, and it’s just one tool in the arsenal.

CuriousFox

WR Officer

2

🦊

Interesting. My company hadn't mentioned using AI. Not for or against. 🤷‍♀️

Sunbunny31

Politicker

2

Sr Sales Executive 🐰

We are leveraging it (and honestly have been) in our solution, so being able to comfortably use it and articulate value is important. And our use makes sense. ChatGPT’s public version is fun, but limited and pretty predictable for what I’ve been doing with it. Limited being the key word.

ConwayStern

Member

2

AE

Yeah, I think one of my biggest challenges right now (aside from building a sales org form founder-led) is really understanding how to fit in under the founder. Not in a supplicating way, but as @CadenceCombat pointed out sometimes you just need to keep your mouth shut, let the person say what they need to say and focus on results.

CadenceCombat

Tycoon

4

Account Executive

I’m going through something similar and the way I’m trying to navigate it is to remind myself that my big mouth can get me in trouble and keeping it shut right now still leaves me with all the same options I currently have.

Even if it comes to a breaking point where I do need to speak up, we haven’t reached that point yet, so why play my hand early?

Hope this helps. That’s all i got.

ConwayStern

Member

1

AE

+1
something I need to be better at anyway as I / my family definitely trend towards being outspoken or contrarian, but I'm the first to really have an office job (parents were school teachers/tradespeople). sometimes the simplest advice is best!

oldcloser

Arsonist

3

💀

Oh, dude, I so empathize. You worked all weekend, pulled what you could out of sparse data and made it make sense. Presentation time comes and CEO wants to have a chatbot replace the effort.

Reality: Chatbots are a dime a dozen. GPT happens to be the most well-fed currently, but it doesn’t do anything that isn’t purely generative. It’s not cognitive. It does not think. Its a well-studied idiot.

If he wants predictive insights from your data he needs an ML solution. And I’d love to sell him one.

Either way, what he’s asking is not reasonable. I guess you have to explain this to him in the right kind of way.

ConwayStern

Member

1

AE

We'll continue this in DMs but as early as after our Series A I could see him wanting to build out our data capabilities 😉
As an update, we've had a few talks about this over the last couple of weeks and most recently he's been very understanding. They're tough talks at times, which is unavoidable, but it's allowing us to grow. He's a great leader, I'm lucky to have him!

oldcloser

Arsonist

0

💀

That’s great to hear! You go

pirate

Big Shot

3

🦜☠️ Account Executive

Ah I'd be annoyed too

Perhaps phrase it like:
"Me and you both this want this to work. I spent x hours doing this and it is hurtful to hear that AI could do it in minutes. GPT can not do this yet. I can. I feel a bit upset "

I think CEOs are great but they are generalist. Great at big ideas and inspiring people. Not so great in actually understanding what something like that involves in detail. You are a team

ConwayStern

Member

1

AE

I said that in not so many words and we talked it out. I basically just got out of ramp, shadowing him on calls and learning the product, so there have been growing pains as I establish my own lane that inevitably is different than how he operates.

Maximas

Tycoon

2

Senior Sales Executive

I definitely feel for you on this!
Perhaps his response could've been nicer to appreciate what you've done!
My response to him would've been like "We all know that GPT is pretty useful in that regard but the keyword here is the Personalization of that sales process and stage/exit criteria matrix to typically fit our company's employees in particular, therefore these studies and taken notes would definitely benefit the firm more than anything else".

detectivegibbles

Politicker

1

Sales Director

Out of curiosity, did he ask you to do this?

Or, was that the point of your post…you wanted lead up the ladder and show value?

ConwayStern

Member

1

AE

He did ask. Admittedly I have been making mistakes of my own (misunderstandings in communication, etc) but I'm chalking this all up to growing pains. It truly does come from a good place, but his background is high finance sweatshops so his default management style, while rapidly improving, is still very, *very* blunt at times.
Nothing that can't be fixed with some reps and getting a thicker skin.

AnchorPoint

Politicker

1

Business Coach

I think you said it all with "working AS his head of sales."

ConwayStern

Member

0

AE

Fair point!

CPTAmerica

Opinionated

0

President/CRO

Pretty common when working directly for a founder. Sounds like you're in a good position overall, in that you can share your thoughts directly with him and he will do the same in return. Doesn't mean you will always agree but it does mean the lines of communication are open and that's a very big deal.

Let this play out a bit and see if your assumptions turn out to be true. Also, don't forget to be open to the idea that you could be wrong. Confirmation bias is a real thing and it can blind you. If you treat each "issue" this way and avoid getting too emotionally invested in "being right" you will likely have a great run together.

ConwayStern

Member

0

AE

This is big. Agreed on all points - I just read David Foster Wallace's commencement speech which conveniently touches on this in a way that resonated with me. Actually, I think I'll make a quick post about it now...

Red5

Praised Answer

0

Head of sales

Let him know you’re not sure how to have accomplished that in GPT and ask him to walk you through and show how you could have done that

ConwayStern

Member

0

AE

There are definitely moments where I should pull this card - other times I'm realizing he's just doing his "big dreamer founder" thing and I should focus less on the specific language and more on the "why" of his asks to come up with alternative solutions.

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