I recently spoke to a executive at a relatively large company who was spending $200,000 on outbound sales tools.

They had Zoominfo, 6Sense, Apollo, all of the legacy providers. Fat annual plans of every tool you think of when you think "legacy software"

This, of course, is before the sales team salaries, the marketing initiatives that drove awareness to the brand, and all of the other residual expenses associated with running a large company's end-to-end sales motion.

Now, you might be telling yourself, this is pretty standard for a large company with a matured outbound motion and several offerings- and I would agree with you.

But here's the kicker: they weren't generating a single lead from outbound. Not one. For the past few years, they had been relying on exclusively word of mouth to drive revenue growth, which was great, until the hype died down and they were left with no idea how to sell. I was shocked when I heard the words "no leads" come out of his mouth. Like, you're spending millions of dollars a year trying to sell a service that you KNOW people like, and you didn't get one person to convert.

Now, this is a pretty insane edge case- like usually, you're at least getting something. However, I think the sequence of events that caused them to get there is not rare, and in fact, quite common in large sales teams. Here's why I think this happens, and how you can fix it:

When you're running lean, it's easy to ideate, iterate, and optimize outbound without running into the throngs of bureaucracy that hinder your creativity. When the founder is leading the sales motion, they're inevitably just trying every type of copy under the sun to get a prospect to bite. They're doing LinkedIn outreach, cold calling, emailing, and offering everything from a free audit to airpods to get someone on the phone.

On the flip side, if you're at the helm of a sales organization at a $10B company, you don't have nearly the same amount of autonomy- not only because you're probably not the only decision maker, but because every major change in your sales org will ripple effect across the entire organization. One small change in tooling could make you lose jobs, hire 10 more people, or retrain your whole team on how they do the thing that they've been doing the exact same way for the past 5-10 years.

This isn't necessarily a problem if all else was held the same. For example, if Apple started with Steve Jobs selling the Apple 1, and he found message market fit, and then scaled that exact strategy for that exact product to the entire organization, then you'd have a scaled version of something that's working. Great. More people doing the thing that works = more sales.

But in reality, this is never the case. The strategy that the founder was able to formulate in the beginning becomes obsolete within 2-3 years of developing it. Either the messaging gets played out, outbound restrictions increase, the product/offering changes, or a slew of other things occur to make it not work. Think of email marketing when it first came out. You could just blast 1,000,000 emails to everyone in your ICP with no restrictions and no personalization, and just print money. Try that now and see what happens.

This leads to sales teams essentially trying to "innovate" with their outbound without actually doing it. The way to do this? Buy every sales tool that the market tells you to buy.

Of course, this does nothing most of the time. If their copy and strategy sucked before, then it's certainly not going to work at scale, or with higher intent leads, or with whatever the latest tool is telling you it can do. Funny enough, the founder in the situation I presented earlier would fare better with those tools than the massive company. At least they can learn to use them correctly.

A perfect example of this is with the case of Clay. If you've been on LinkedIn at all in the past year, I'm sure you've heard of it. It's the most hyped-up product I've seen in the market, and it should be. It's genuinely one of the greatest innovations in sales tech probably ever.

People who are using Clay correctly go on LinkedIn, hype up the tool, which spurs sales leaders at larger companies to buy it. Why not, right? They have unlimited budget and it seems to be the answer to all of their prayers, at least it was for the people online. They watch a video or two on it, create a few personalizations, and run a campaign, which of course flops. Their strategy didn't change at all- the vessel for their bad strategy changed, which still delivers a bad offering.

So, how do you fix this problem?

In my experience, the answer is this- hire 1-2 people to strategize your outbound, hire a small team to manage the tools, then hire a large team to manage the rest. I don't care if your ARR is $1M or $10B, this rule still applies. The further down the funnel you are, the more people that should be tasked with managing it.

Here are the types of people you need to hire if you're a Head of Sales in the modern day:

An outbound strategy wizard: Find the most publicly good person at outbound strategy online and pay them as much as they want. This is usually someone who maybe used to be Head of Sales, but find one that's willing to be back in the trenches for a price. They should focus solely on the most creative outbound ideas possible. Don't manage them at all. Seriously. Let them act like a founder does in the early days.

An Automation Expert: Top of funnel initiatives like outbound can now be automated by 1 person with 200mg of caffeine a day and a Clay subscription. If they're good, any idea that the outbound wizard comes up with can be sent at scale, and tested quickly.

Mid-funnel SDRs- the SDR is not dead, contrary to popular belief. The outbound wizard and the automation expert should be sending all of their bites to this person to manage. There don't need to be that many of them because half of their job is now managed by the aforementioned dynamic duo.

AEs- this is pretty much the same. Make sure they know the product inside and out. This should be the largest group by headcount out of the whole organization, as you can't (at the moment) replicate a good human touch in the sales cycle.

This setup is great because it allows for flexibility in strategy and tooling, while maintaining a reasonably mature sales process and headcount on the bottom end of the funnel. The two people coming up with all of your creative ideas run loose while the structured closing org churns out conversions.

In short, if you're spending money on tooling without changing your strategy, then cut everything and go back to square one. What works at a small scale works at a large one, so invest in smart people and strategy and cut back on tooling. When you get something that works, throw as much money into tooling that allows for scalability as possible.

Oh, and the company I mentioned before? We've gotten them $20m in pipeline in the first 4 months of working with them. We acted as the outbound strategist and automation partner, while their team did the rest.

It can be incredible when people who know a product well are combined with people who know the tech necessary to sell it 🚀