By Samantha Hulkower, Fractional CMO and Head of Marketing, KSW Solutions
As a fractional CMO, I get a view that most people don’t – I’m inside multiple companies at the same time, of different industries, sizes, and stages. So, after a while, the patterns become impossible to ignore.
The one that keeps coming up, more than anything else? Leadership is not taking sales planning seriously for small business owners.
Not because they don’t care about revenue, what CEO doesn’t want to make money?! But somewhere along the way, sales turn into something they hope will happen, rather than something they can forecast. The team is busy, the pipeline looks full enough, the calendar has events on it – so it feels like things are moving. Until they’re not.
I might be a marketer, but I happened to be partnered with a great sales leader and Chief Revenue Officer. Working together at our sales and marketing consulting company has granted me a behind-the-scenes look at sales, which has influenced how I manage marketing (more of an emphasis on “Is this supporting sales” and less “We need to do these things for visibility”).
It’s also helped me to spot bad sales processes where I’m working.
I’m sharing some examples of of bad sales planning not to shame previous clients (I love my clients!), but to hopefully strike a cord with some of you who may identify your own bad sales planning, and perhaps get some takeaway lessons on how to improve your sales (and ultimately increase your revenue) for small business owners.
Sales Team Not Using the CRM – Let’s Get Rid of It!
One client I worked with was fairly big, 60 staff members across the globe, 7 salespeople. Like any business, they have a CRM, but like many businesses, the salespeople weren’t very diligent about keeping it updated. Most kept everything in their email. Their sales team had a CRM, but maybe one or two of the guys used it. The rest were managing everything through their personal email.
The CEO noticed. Now, a CEO who is heavily in involved in sales would have noticed a lot sooner when he tried to check the pipeline forecast and saw it empty. But this CEO was only a CEO because he founded the company, and he happened to be an engineer with a product that at the time sold itself. So for years he didn’t notice.
In theory, his logic was reasonable: if the salespeople aren’t using the CRM, and we’re still making sales, why are we paying for it? So he got rid of it and let the team keep doing whatever they’d been doing.
I had left the client for a period of time, and when I returned and wanted to send a newsletter I discovered that the system no longer existed.
Now, this is a lot bigger than no more newsletters (which by the way, are a huge source of upsells for a variety of industries. Remember, it’s always easier to sell to someone who is already your customer).
It also concretized what was previously just a lack of sales process implementation. Now no one could say, where leads where coming from, which deals were stalling, which salespeople were performing well, or give any sort of revenue forecast.
The CEO was penny wise, but pound foolish, looking to save money in the short term, which actually caused a bigger problem (and probably cost the company millions in the meantime): a discipline problem and a complete data blackout.
The CRM wasn’t the issue. The culture around using it was. Getting rid of the tool doesn’t fix the behavior, it just means you’ll never have the information you need to forecast, plan, or scale.
If your team isn’t using your CRM, the question to ask isn’t “do we need this?” It’s “why aren’t people using it, and what does that tell us about how we’re managing our sales process?”
Showing Up Somewhere Your ICP Is Doesn’t Mean You’ll Reach Them
Another other client sold industrial equipment to enterprise buyers, the kind of product that ends up in large facilities, warehouses, and manufacturing plants. When their salesperson flagged an industry conference as a must-attend event, I wanted to look a little deeper myself. I always look to sales to help identify the best events, but since events come from the marketing budget, I always want to verify that the spend will justify the investment.
I looked a little deeper, and thought okay our ICPs will be there, but does it make sense to exhibit?
The event was high level manufacturing for an industry. My client produces on component that is used in these sites. The people participating in this even are not interested in nuts and bolts, they are looking for complete packages – of while our product could be a part.
I pushed back and said that I think it makes more sense to visit the event, not participate as an exhibitor, since our product isn’t something that participants will be interested in this event, but there will be vendors at the event who would partner or buy from us, so visiting gives us the opportunity to walk around to talk to them and have meetings. A booth puts you in a passive position since you’re waiting for people to stop, and you don’t know who will or won’t walk past in a large exhibition hall.
The salesperson pushed back. He went.
He did not come back with a single order.
Now, he could have gone as a visitor and still not come back with a single order, but it wouldn’t have wasted so much marketing budget to do so. And it would have been easier to visit booths of our ICPs instead of hoping they will come visit him.
Sales planning for small business owners means asking ROI questions before you write the check, not after.
Sales Doesn’t Just Happen
Both of these situations have the same root cause. Sales planning for small business owners is often treated as something that happens on its own—as long as you have a team, show up to events, and keep busy, revenue will follow. Planning feels like a formality, forecasting is seen as just guessing, and no one takes the process seriously.
It’s not necessarily that the companies that scale simply have a better product. They have better systems that are transparent and show where their deals come from. They know which activities produce pipeline and which ones just feel productive. They make decisions based on data, not gut feel and whoever pushed back hardest in the last meeting.
You don’t need an expensive CRO to start thinking proactively about your sales. You just need to get out of your comfort zone and start asking the right questions before you make sales decisions – not after the booth is booked or the CRM is cancelled. The questions that might be hard or uncomfortable to answer (which is why you’ve been avoiding them), but that are holding you back from growing your business.
Ask yourself: What does your pipeline actually look like right now? Where did your last five clients come from? What’s your close rate, and do you know why deals are falling through?
If you can’t answer those questions, you don’t have a sales problem. You have a planning problem. And the good news is that one is a lot easier to fix than the other.
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