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This week I've been working with a founder who has a team of reps and a plan to grow by adding more of them.
It's a good team. They're organized. And their reps are struggling. They asked me to help them figure out why.
Here's what I see: they're overinvesting in reps and underinvesting in sales management. I see this pretty frequently, so I figured I'd lay out what good sales management actually looks like from an organizational design perspective. The big pieces, what each one does, and what it costs.
The short version: don't underinvest in sales leadership. Even if you only have one rep, you still need to do most of this. If you know what it costs ahead of time, you can plan for it. If you don't, you end up with underperforming reps and no idea why.
Start with the design
Most of the struggling reps I meet in startups aren't failing because they're bad at sales. They're failing because the organization didn't give them the structure, the process, and the tools to be successful.
It helps to think about what's in the rep's control, what's in the manager's control, and what's in the organization's control.
The biggest thing in the organization's control is product-market fit. It's the largest multiplier you can possibly have. Every salesperson already knows this instinctively - if everybody needs the product, it's easier to sell. But it’s only the first part.
The product market fit layer defines the market you serve, the gap you’ve found, and how you solve it. The sales organization design stack is what follows, and looks like this:
The right roles
The right people in those roles
The right process for those people to run
The right onboarding and training to teach them that process
The right technology to enable that process
The right checks to make sure people keep following the process, understand it, and keep getting better
Today I'm focusing on process and sales management. But I figured it was worth laying out the whole picture, because a gap anywhere in this stack shows up as a struggling rep.
Process is the firmware
Everybody knows the word process. I don't think most people know what a good process means for a sales team.
It's more than "here's what you do on a call" or "here's how you handle a new lead." Your process is how you communicate your strategy to the sales team. It's the firmware. It tells them how to operate, what to do, what their goals are, and what's important.
That means the high-level guidance too. Go after these types of accounts. Talk to these people at those accounts. They're going to care most about these things.
Remember, your sales team is executing the vision you gave it. They're running on the market need and solution hypothesis you handed them. If you didn't give them that guidance, your results are going to be completely random.
Now, my client didn't have a strategy problem. They had a sales management problem. But it wasn't a problem with the sales manager. Their manager was split across two roles and didn't have enough time in their calendar to do what the team needed.
Spending isn't investing
That's the trap a lot of founders fall into.
You might be thinking, "I've got six reps. I'm spending a fortune on sales. How am I underinvesting?"
You're right. You're spending a lot. But spending money on reps isn't the same as investing in making them successful.
It's a bit like poker. There's the minimum buy-in to sit at the table, and then there's the amount you actually need to avoid getting pushed around and losing your stack in twenty minutes. Not that I'm any good at poker. I know I'm a fish, so I stay out of that pond.
A lot of founders hire a rep, assume they're a sales professional, and expect them to figure it out. They figure they’ve succeeded somewhere else and that was because the individual rep was amazing. But a rep’s results at their last company had as much to do with that company’s product-market fit and the support system around them as with their own skill.
They still need a lot of hand-holding in the first 90 days to learn how to sell your product, and feedback and adjustments long after that.
Yes, there are a few unicorns out there. Full-cycle reps who can figure out your product, hunt their own deals, and generate magical amounts of revenue. They're few and far between. Don't build your sales plan on hope and unicorns.
The five weekly jobs
Here's what a manager needs to do for every rep, every week.
First, the one-on-one. This is the personal and professional check-in, 30 minutes to an hour. It's also your energy check. How are they doing? How are they feeling? Underperforming reps can easily slide into a spiral. Oh no, they're going to fire me. Oh no, these deals aren't going to close. That negativity feeds on itself, and it shows up on their calls. Some reps need more encouragement than others, but your one-on-ones need to watch for this every single week.
Second, answering their questions. Sounds obvious. It still takes time.
Third, call review. Have the rep bring their best call or their worst call. Ask them where they think it went wrong before you tell them. Where they look tells you how advanced they are. Plan on at least an hour.
The trick here is the golf pro problem. If you watched me swing a golf club and listed twelve things I was doing wrong, my next ten shots would be worse. The manager's job is to absorb everything you see them doing wrong and hand back one thing to fix this week.
Fourth, pipeline review. This is one-on-one too. You sit down with their pipeline and work the deals together. Where are the gaps, what's stuck, and what's the next step.
Fifth, targeted training on whatever that specific rep needs right now.
On top of that, there are two team-level jobs. The first is a forecast call, where the team rolls up which deals will close and which won't, so you can tell your senior leader something real. That's different from the pipeline review. One is about working deals. The other is about predicting them. The second is a weekly team training, built around the common theme you heard in that week's one-on-ones. A short presentation, then roleplay.
And every one of these needs prep. A rule we used to live by: an hour of meeting needs an hour of prep. If you have five hours of meetings with a rep, you need about five hours of prep. Otherwise you're showing up unprepared and winging it on the rep's time.
The math
Here's where founders get surprised.
Ten hours a week to manage six reps is the bare minimum. Ideally you're spending about two hours of meeting time and two hours of prep per rep, every week. For six reps, that's 24 hours.
Then there's the team training. Preparing a good one takes two to four hours, plus running it. Add the forecast call. You're close to 30 hours a week.
That's most of a full-time job. It's not something a manager squeezes in around a second role.
If you're in founder mode with one rep, you can probably wing the training as a 90-minute session. But you'll end up filling it in with a bunch of smaller sessions through the week.
The quarterly layer
Every quarter, each rep sits down with a development plan. The rep reviews and scores themselves. The manager does the same, separately. Then you sit down together, compare notes, and talk about their goals for the next quarter.
It's about how they want to grow, not "hit my numbers." Their numbers are already their numbers.
This one is probably its own newsletter. If you want to hear more, reply and let me know. I'm happy to share the process we used across the whole company at Predictable Revenue.
Back to my client
They run on EOS, and they run it well. But EOS doesn't have a structure for sales management. What you just read is basically the process guide I put together for them.
So here's my challenge. Count the hours you, or your sales manager, spent actually coaching reps last week. Is that the full buy-in, or did you sit down at the table with the minimum?
Collin
PS - I’m looking for one or two more folks to join the Predictable.ai beta next week, if you’re using LinkedIn to find conversations, I have something interesting to show you.
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