To start, a note of credit to the great Jim Herbold from Box.
He was my hands-on mentor for many years. Bolt sales would not exist without him.
Much of this is learned wisdom from him.
Ok, here we go 👇
1/ Close the first deals yourself, end-to-end
It’s impossible to now how to construct a sales team without first knowing how to conduct a sale.
Some founders try to hire before this step.
Doing so is skipping a crucial step of getting intimate with your product and customers.
2/ Document the learnings
At Bolt we wrote a 50+ page sales playbook which included
- Email scripts
- Cold call scripts
- FAQ and Rebuttals
- Negotiating tactics
- Closing tactics
With this handy, new salespeople ramp 3X-5X faster.
3/ When ready, always hire in pairs
If you hire just one salesperson and they can’t sell your product, you’re in trouble.
Why?
You don’t know if the problem is the person or the product!
Hire two, and you have a point of comparison.
4/ Hire for results vs charisma
The best salesperson may not fit the mold you have in your head.
In fact, few salespeople are alike.
All our best have had completely unique personalities.
The common thread: deep thinking, authenticity, and ability to close.
How do you test for results?
Ask about quota performance over recent years.
One or two bad quarters is fine and signals honestly.
The best don’t shy away from this ask.
They’re proud of their numbers.
5/ Discern between easy and hard sales
Some products are naturally harder to sell than others.
High technical and integration complexity means harder.
Simple onboarding and inbound customer demand means easier.
Know what camp you’re in and hire sales reps from that camp.
6/ Stay involved
I believe it’s every CEO’s job to stay involved in sales.
Especially in the early days.
As much as we all want to build “sales machines”, it’s only possible after endless repetition.
7/ Get ready for a journey
Figuring out sales isn’t easy.
Expect it to be really really hard.
Every company dependent on sales goes through a sales journey.
And it’s never smooth sailing.
8/ Seek advice
The best thing I did when building our sales team was reach out to everyone I knew in sales.
From VPs to individuals sales reps in my network.
I asked endless questions and learned a ridiculous amount.
Oftentimes the reps on the ground were the most insightful.
9/ Experiment with pricing
Creative pricing is a sorely under-discussed topic.
There are likely ways to modify your pricing.
Nail this, and pricing turns into a sales accelerant.
10/ Refine sales comp plans
Getting sales comp right is also paramount.
Design it to incentivize behaviors that are aligned with core business objectives.
And keep it simple, or design a calculator, so that reps can easily estimate how much they’ll make on a deal.
11/ Don’t experiment too much
Changing pricing and comp plans can create chaos and confusion.
Experimenting is important.
But watch out for doing it too much.
Doing so creates perceived instability, which can demoralize a team.
12/ Roll out the red carpet
Most companies are afraid to over-pay top performers.
Don’t be.
Accelerators allow your top performers to earn outsized commissions.
That’s a GOOD thing because it only happens when they’re delivering outsized results.
And that's it!
The wildest part: poor sales results aren’t always a result of bad Product Market Fit.
You can have great PMF but terrible sales acumen.
Is it sales or product that’s broken?
This question is what makes understanding PMF so ridiculously hard.
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I am 27 and have built 2 unicorns. My mission is to get the world dancing & fix corporate culture.
Twitter is where I share my learnings.
Let’s take off together! 🚀
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Not really. We’ve found them to be the most powerful tool in our talent arsenal.
Here’s the playbook on how to do an A+ reference check 👇👇👇
Why are references important? 3 reasons:
1. Evaluation: It provides us with critical information 2. Alignment: It creates a tighter hiring process 3. Communication: It gets the candidate excited about the company
#3 is counterintuitive. Here’s what I mean:
Depth of a reference call makes all the difference.
A simple checklist of questions? Annoying, bland, cumbersome.
Thoughtful two way questions? Candidates step back and say “Wow. If the company cares about me this much now, imagine when I’m there.”