I can always tell when someone is hiring sales people for the first time.
They typically make 3 rookie mistakes:
1) Hiring a VP as their First Salesperson
Good VPs want to build teams, manage them, set strategy, and help with the most important deals.
Good VPs DO NOT want to do the dirty out bounding, follow-ups, contract redlines, etc…that come with early stage sales.
If you need help building some operations or strategy, then hire a good sales consultant. They’re going to help you avoid some very costly mistakes.
And make sure your first hire is a full cycle AE that can prospect and close.
2) Complicated Commission Plans
I’ve built dozens of sales compensation plans. I used to worry about every scenario…how do I protect the company? How do I protect the reps?
The plans got complex. It cost the company company countless hours of expensive time trying to calculate every detail and manage the one off scenarios with the team.
Don’t do this.
Instead, keep it simple.
- Your first plans should not include escalators, just flat rates
For SDRs specifically:
- Start with a commission for each meeting held and try to add a commission for each deal closed (if you can)
- In the beginning, don’t penalize them for bad meetings set, but monitor it closely. Eventually you can add variable that measures the % of their meetings set that AEs mark as Sales Qualified Opps
3) Missing Obvious Red Flags in the Hiring Process
A bad first hire will cost your executives a lot of time and a lot of actual money for the company.
At a bare minimum, your first hires should be excellent with the small details around communication — good formatting, proactive, professional.
You’re hiring sales because you need to get it off your plate. So while you’re juggling everything else, you don’t have time to train someone on the fundamentals of client communication.
How they communicate with you during the interview process is a reflection of how they communicate with customers.
Even if the candidate has good logos on their resume, don’t drop your standards on communication.
The reason this is top of mind?
We've been hiring a bunch of overseas SDRs for our clients and I've been having these exact conversations with founders and early stage managers.
The bar for Customer Success is LOWWWWW
We pay for an ATS...it's a core software for a recruiting business.
1 month ago our usage rate fell off the map.
The company never reached out.
1 week ago we downgraded our subscription by 80%.
It took them a FULL WEEK before they reached out.
And they didn't even call me.
Just sent an email and hoped I replied.
Great CSM teams are constantly assessing account risk and being proactive about things going wrong.
IMO, the best CSMs are like great salespeople. Hunting for problems and expansion. Never reactive.
Don't be like these guys.
There are two types of employees.
One sends you homework.
The other sends you answers.
Guess which one gets promoted?
The homework type forwards you a link and says "good read."
That's not help.
Now I have to open it, read the whole thing, and figure out why you sent it.
You moved the work off your plate and onto mine.
The answers type sends the same link, but they did the thinking first:
→ What they learned
→ Why it matters
→ How we could use it
→ Why I should care
Now I can act in 30 seconds instead of 30 minutes.
Same thing with your calendar.
The homework type sends "can we talk?"
About what?
If I don't know the topic, I can't prioritize it, so it sits at the bottom of my list.
The answers type sends "want to talk through the pricing change and how it hits Q3."
Now I know if it's a hallway chat or a real meeting.
It's about doing the thinking so the other person doesn't have to.
The people who send homework stay where they are.
The people who send answers move up.
I've spent 11 years hiring GTM for venture backed companies. 3 years ago, I used all of those lessons to reset how people hire overseas talent.
https://t.co/V9m6Nhhowb
Sequoia, Insight, Lightspeed, Y Combinator, IVP, GGV...all have 1 thing in common.
Their portfolio companies are using Remote Growth Partners to build out their GTM teams overseas.
Having an AI engineer on your team is an unfair advantage.
We manage outsourced sales teams for tech companies.
This week, we built a new custom dashboard for a client who has 10 SDRs because Salesforce was being a pain in the ass.
The data is exactly what we wanted.
It's interactive.
The client loved it.
We're just starting to cook...
Why are CPAs so bad at sending invoices?
It's always an email from 1999 that looks like my identity is about to be stolen.
Subject:
Boris Smith & Associates LLL has published REMOTE GROWTH PARTNERS 2025 INVOICE - DUE UPON RECEIPT.pdf
Who tf is going to open that email?
5 ways to f*ck up a sales interview as a hiring manager:
1. Say "Tell me about yourself"
→ lowest value question you can ask
2. Don't research the candidate's background beforehand
→ prep is a two-way street
3. Wing the interview questions
→ each candidates need the same questions to be objective
4. Don't know your own team's numbers or try to hide them
→ if you don't have these, you're the red flag
5. Skip the hard questions because you "got a good vibe"
→ sales people are good at selling themselves, trust but verify
The best sales managers are intentional about every part of their interview process and they tend to know their shit.
What else did I miss?
Claude Cowork is so bad for my sleep.
Been wanting to have a better way to track overdue A/R status and the latest efforts on each outstanding item.
I should have gone to bed at 10PM, but I started a chat a 955PM.
Now I have a A/R Chase tracker web app that I can share with my finance team.
- imports live data from Quickbooks
- set the status on each customer
- leave timestamped comments to track updates
Not bad for a v1 from a non-technical founder.