131 founders. 300 conversations. 74 contracts won. Here’s what I’ve learned about building and scaling sales teams.
I have won 74 contracts and lost 57 in less than 2 years.
This means I have deeply spoken, evaluated and learned about 131 founders who needed to build or scale their sales teams.
I talked to them at least 3 times (before issuing any offer) - which makes it >300 deep interactions.
All of them had something in common:
they were selling all B2B
they were <5M ARR mark
they were founders who needed to build their first sales team or make the one they had better.
Like most tools or services also, mine (fractional sales leadership) answers 90% of the time to the same problems:
I want to build my first sales team, and I don't know how.
I want to scale mine since things are not working as I expected.
So, let's say that the scope is very similar from one to another.
If you meet me in the street and ask me, "Matte, I need to build my first sales team. What did you learn so far?".
Here is what I would answer.
Inbound vs Outbound
If you can start driving an inbound sales motion right now, please do it.
Building in pure outbound is:
expensive
time-consuming
expensive and time-consuming together!
Jokes aside, inbound is critical.
Whether it's referrals or conversations starting from content, you put it out there (I highly recommend writing on Linkedin or a newsletter).
If you are targeting small business owners who frequently use Facebook, starting some ads on Meta (which usually has low CAC) would also be a good idea, along with Google ads.
But your CAC has to be low. Otherwise, you'll have to go the hard way.
Start posting consistently on platforms like Linkedin, telling your stories to your ICP (ideal Customer Profile).
If you must do Outbound, start 1:1, not one too many.
Go to Sales Navigator, save your top 200 decision makers, and engage effectively with each of them based on insights or signals.
Drop the one-to-many approach, at least until you know your ICP well, or you have a large SOM to target.
Average deal size >5K ARR
Sales led below 5K ARR is challenging.
It doesn't make sense in the long run.
It does, at least initially, if you can keep your CAC low.
But only 10% of companies can do that.
If you sell <5K, try everything you can do to sell:
through your platform on self-service
through channel
Keep the juicy Enterprise or MM (mid-market) tiers for your sales team and try to systematise the SMBs. (small and medium business).
They are okay when you are learning your product and market, but as soon as you get some sales motion, try to focus on bigger tiers if you can and if they fit your product/service.
If you want to build an SMB team, that's okay, but stay as close as possible to the 5K mark.
3X Ratio Cost / Revenue
Keep a good ratio between your expenditure for sales & marketing and revenue. Usually, for small startups, 3X is a good start. Which means:
A salesperson cost me 50K per year
They should bring at least 150K per year
This is true when setting up your budget and a sales goal.
A goal too high for a low-paid resource is not fair.
Remember the rule of 3X, and you won't be wrong.
When you scale (>5M ARR), you can push this to 4X or 5X.
Communication is Key
This is the most underrated takeaway. Communication.
Scattered, WhatsApp, emails, chats.
Messy. Wrong.
Set up Slack - forget Teams or Google Chats - right now.
Slack is the best tool for hybrid sales teams. No questions. (I have no affiliation.)
Build channels, canvas, and automation, and run your office on Slack. You have limitless integration with all your tools, including productivity and CRM's.
Start now if you can, and trust me on this, regardless of your view.
Since 2018, I have worked and managed hundreds of salespeople remotely or hybrid. Slack is key.
But remember to set it up right: threads, channels, slack netiquette, and all otherwise, it becomes another messy process.
Final thoughts
Building and scaling your sales team is critical. Yet, it can be challenging for technical founders with little commercial background.
But it's not impossible, and it's repeatable.
If executed correctly, you can learn how to do it and repeat it consistently.
Thanks for reading this far. I will see you all next week.
