Commercial planning survival guide: Part 1 - You (might be) planning too late

The argument for early commercial planning

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It’s August, so that means planning season is around the corner.

The problem?

All of the content out there around commercial planning is incredibly dull.

Either it’s focussed on the budgeting process and Finance. Or it’s a step-by-step guide on how you can end up with a set of commercial “OKRs”.

That’s all incredibly surface level and won’t teach you anything ChatGPT can’t already tell you.

And the truth is, very little advice out there actually deals with the GTM side, let alone how to navigate planning in today’s fundamentally different environment. 

That’s why this month I’m running a 3-part series on the pains of planning, and how to make it better.

Make sure you’re subscribed to not miss the series:

• Part 1: You (might be) planning too late (this post)

• Part 2: Penetration test your plan (next week)

• Part 3: Closing the gap

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If you’re starting commercial planning now, you might feel like you are out in good time. 

And you might be. But you also might not. 

The reason is that people don’t actually think about when they as a business should start this process. 

I mean, why? Finance starts this in October… so that’s when we start it too, right?

Think about it like this: 

• If you want to have some new folks join in January, when do you need to start hiring? 

• Or if you need to get this CVR to improve in Q1, when do you really need to start working on it? 

• Or if your Q1 target requires you to increase your pipeline by 50%, when should that happen? 

That’s right. 

Some of you might say, well November is ok. 

Others might say, shit, I need that pipe to be prepared in August. 

So what’s the difference here? 

Your Sales Cycles. 

Let’s say you have proper enterprise sales cycles of 6-12 months. If you start planning for 2025 in November, there will be VERY little that you can do to actually impact anything next year. 

• AE hires will have a year-long ramp up. 

• Initiatives will result in revenue only +6 months in. 

• Pipeline should have been built 9 months ago. 

So realistically, you need to start planning 1 full sales cycle before the new year. 

If this accidentally perfectly aligns with when finance randomly decided to do the planning, then great. You don’t have this pain. 

But for everyone else you not thinking about when you should be starting to plan has real impact. 

This all Finance’s fault (kinda)

Let’s be clear. Finance owns planning. They start because they work backward from their needs, which really are to get a budget approved by the board. 

If you are part of an early and small team you can get this done in a month. Later it will take longer. 

Your planning need is really not their problem. And since you aren’t even aware yourself, how could you blame them for not knowing?

And this leaves you with the next problem. Let’s say you are aware (you’re welcome), you won’t be able to get finance to kick off planning just because you said so. 

This is a massive undertaking for finance and Oct-Mar is called the “busy season” for a reason (next year’s budget & this year’s annual report). 

And if you plan for next year before finance does their part, it’s usually pretty useless. 

You won’t know which number to aim for, nor will you know how much money (CAC) you have in order to achieve it. 

So whatever you do it’s going to be wrong - and then this process will seem pretty useless to whoever is involved. 

So, what should you be doing? 

If your Sales Cycle matches the timeline that Finance does planning in - you are good. 

If your Sales Cycle is longer, consider the following options: 

1. Ask your CFO for a rough forecasted budget. 

They usually can create a rough plan for you. Obviously with a lot of caveats. But at least it will give you an idea of where you need to go with how much cash. 

2. Ask finance to do 2-year planning 

This way you can follow the normal planning rhythm late in the year, but you then have actual numbers for the following year. This way you can freely choose when you want to start planning. 

Sure numbers will change for next year. But again, this will give you a good enough understanding that you only need to adjust slightly later on. 

3. Ongoing 12-months-rolling plan

This is what the real commercial pros are doing. 

As sales updates their forecast every week. These folks update their 12-month rolling plan every quarter. 

You get new data in, you have learned a few new things, you now know more about your business than previous Q.

All of this should be incorporated into your next planning window. 

And as you do this, you will always have initiatives that are more clear short-term vs long-term. 

By keeping your plan aligned every 3 months, you can continue to break down longer-term fluffy initiatives into tangible short-term actions you and the team need to take. 

And obviously, to pull this off, you need to have a two-year plan in place from your finance friends. 

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On the podcast this week

• Are you "on the bench" looking for a new job in b2b SaaS? Don’t know if the next place is the right fit? Do this before you accept a new offer.

• Our guest series is back! We sit down with Wes Bush of ProductLed.com to talk about why PLG sucks and how to fix it.