Thriving in B2B Sales in an Economic Downturn

In this live session, I walk through my formula for surviving through b2b sales in an economic downturn and the seven things you can do to actually thrive based on my previous experiences in hard times. 

1. 1. Mindset (winning is possible)
   2. Business conversations over product conversations
   3. Packaging solutions vs. product proposals
   4. Speak the customer language (put ROI and key talking points in their language)
   5. Use your internal team to move up the ladder
   6. Don’t get desperate
   7. Hard pivot messaging

Hear real-world examples of how in 2008, I led my sales team to over 100% to target, and we were the #1 team out of 20+ sales teams. Then again, in 2020, when COVID shut down the world and many sales leaders were saying that “nobody is buying software right now,” Q4 was Skaled’s best quarter of all time.

But why?

As we enter into the next economic dip just two years removed from COVID, now is the time to prepare your sales organization not just to survive but thrive.

Transcript: Thriving in B2B Sales in an Economic Downturn

What I thought I’d do today is spend a little bit of time talking about my experiences in B2B sales over the course of the last 15 years or so that are the most applicable to this time: what we’re going through now, my own experience, and things that I saw firsthand during the economic downturn. 

I’ll also try to give a lot of tactical advice for all of you who are in B2B sales and trying to figure out what does this means for me? 

We’ve started seeing the layoffs happen on LinkedIn for a little while now, and I think when Elon Musk came out and said that he’s nervous about the economy. That’s when a lot of people are like, oh crap. If the wealthiest man in the world is making his employees come into the office and is still planning to do some pay cuts, it can feel a little uncertain, and I’m sure for many of you, this is your first time going through something like this.

COVID was a bit of a blip for nine to twelve months, and then we started coming out of COVID in 2021. Aside from that, we’ve pretty much had an economy that’s going straight up into the right. 

And for me, I by no means consider myself a finance guru or Nostradamus in terms of what’s going to happen with the economy, but what I can do is share with you what I did. I’ll share some of my stories and things I did for my organization and team, as I’ve been through this multiple times. Where I’ll start is for any of you who are in B2B sales or Marketing or in that world, understand that these cycles happen.

And it’s really difficult, especially when it’s your first cycle, which for a lot of you, it might be where things have just been going up for so long, and then they’re going down, and you’ve never seen been a part of that cycle before. This happened to me back in 2007, ’08, and ’09. I had just started at a company called CareerBuilder in 2006. And at the time, CareerBuilder was the largest job site in the world. Linkedin was just a social networking site that had just started, and monster.com was another big player. 

And interestingly, I think I had the gift of being naive, and I didn’t really know what an economic downturn looked like or what it meant.

#1 Mindset (winning is possible)

So the first thing I want to tell you is that your current mindset will directly impact your success. If you want to see doom and gloom, “Oh, people are pulling back and not buying,” or acting like it’s not happening, I can tell you my number one piece of advice during this time if you’re in B2B sales, is mindset and that mindset is winning is possible. 

I don’t know how many of you have seen the stories or these things happen, but if you look at COVID as kind of our most recent blip, COVID wasn’t a full-on downturn, but there were parts of it where things did collapse. Such as whenever we first all went to work from home, but it came back within about seven or eight months.

Having the right mindset that winning is possible to me is one of the most important keys to success if you’re in B2B sales. So for all of you out there who might be thinking, “Oh man, what does this mean?” You can only control what you can control. So don’t worry about it. Just understand that winning is possible. Plenty of people will win, and some will win really big regardless of the industry. 

#2 Business conversations over product conversations

So the second piece of advice I want to hit a little bit on is when I started at CareerBuilder in late 2006. Like I said before, largest job site in the world at the time.

I moved into sales leadership in early 2006. I ran a team that ran the Pacific Northwest territory. So there was nothing special about my territory. We had Washington, Seattle, Idaho, Montana, and a few other areas. But long story short, the economic downturn forced our team to get better at having business conversations. 

This was a huge one for my team. And so what do I mean by that? Imagine there are two different ways you could pitch. 

Let’s fast forward to late 2007. You may remember Bear Stearns, Lehman Brothers, and a few other companies collapsed. It wasn’t just the economy but the banks. The foundation of the economy is crumbling. 

As you can imagine, people were pausing hiring, just like we’re starting to see now. And like I said earlier, for many of you who are seeing a downturn or possible downturn for the first time, you may be thinking, “Wait, these companies were growing. They hired all these people, and now they’re laying people off?” Well, this is what happens in a down economy. And so, back to 2007, at that time, I didn’t know this. I had never lived through an economic downturn before. 

I didn’t know that it was supposed to be doom and gloom. But I did know that I worked for the world’s largest job site, and no one hiring was a problem.

So let me tell you what we did, and this applies to any of you. Being able to talk to someone about their business and the needs of their business over how to explain a product is what got my team and me through it. 

Between 2007 and 2008, my team was the number one out of twenty-plus hybrid teams, inside and outside sales, in the company. In the two worst years of the economy, my team was the #1 percent to quota, and our territory was Pacific Northwest. It wasn’t California, New York, or Texas that would have given us a natural edge because of population.

And this was 100% due to this second point. I made sure my team was really, really good at talking about business needs over product even in a down economy. Because certain sectors, different groups within an org, they’re hiring. They are looking for talent and have jobs they need to fill. Maybe they need to fill them with contractors now, instead of full-time, but I was really good at instilling in my team that people are still hiring.

People are still looking for people, and I’m telling you, this is the truth, companies are still buying. Software companies are still buying whatever it is you’re selling. And as the economy potentially dips even further, that’s not going to change. 

What’s going to change is the ROI use case, and your ability to have an executive-level conversation becomes absolutely critical. 

So what I trained my team on, and the first question I’d ask when they came to me with a deal, was, “How does this company make money?” If you don’t know what they do, how can you possibly create an ROI case? You can’t. 

For example, say they’re industrial manufacturing. My team would have to be able to say, “Here’s what’s happened in the economy for industrial manufacturing. Therefore, you’re probably looking for these types of people that are really difficult to find. And I can help you to do that.” We wouldn’t have been successful if my team didn’t know these things. 

My number one piece of advice to be able to have business conversations is that you’ve got to start to really understand how your prospective buyers make money. What are the ICPs? What do those people actually do? How do the people actually make money, etc. If you don’t know this, you’ll be pitching product. And I’m telling all of you, if you just pitch product, in this example, there’s a very high likelihood they’ll tell you they’re pretty much in a hiring freeze until further notice, which is what happened to many of my counterparts. 

And so for anybody out there, for whatever sector you sell into, just anchor in this: You have to know what they do and how they make money if you want to survive in an economic downturn. 

#3 Packaging solutions vs. product proposals & #4 Speak the customer language (put ROI and key talking points in their language)

If you know how a company makes money, you can tell an ROI story at an executive level. I’ll give you another example. “I know that you’ve paused hiring for this 80%, but for this 20%, you need these people. Because these people are mission-critical to fulfilling the work you have to do, by working with CareerBuilder, we can do X, Y, and Z strategically. That’s going to help you with our top 10% of roles. In framing conversations like this, we were able to sell contracts that were not just a post-and-pray or a resume database. Instead, people were buying solutions.

And that’s what I’ll put here as number three: packaging solutions versus product proposals. 

They had said this was an issue, and these five things were happening. Here’s how we’re going to put together a package to help them with that, and a solution versus what a product would look like.

What I see with many sales organizations is that if you just send over a list of products, and you even had two or three conversations with people, keep in mind that those people then have to go and sell your solution internally, and in an economic downturn. That’s my fourth piece of advice: you must speak the customer language and put the ROI and key talking points in their language.

It’s going to become harder and harder to sell. In specific sectors, the CFO, the COO, the CEO, and other senior executives will be tight on spending. And so, what you want to do is put together solution-based proposals. If it’s written in their language, it makes it very easy for internal people to go and have a conversation with higher, more strategic people because we’re pinning ourselves and solutions as part of the buyers’ strategies.

By the way, if you learn how to sell this way in a down economy, when the economy goes up, you’re going to destroy it because when the economy’s up, and everyone’s buying, your pitch can be a little bit more product-based, but the money’s flowing and the scrutiny behind budgets are a little bit less. 

So when you cut your teeth in a world where the scrutiny is at an all-time high, and you learn how to have business conversations, you’ll learn how to communicate at an executive level quickly. 

#5 Use your internal team to move up the ladder

But here’s something I also want to call out about having executive-level conversations, I didn’t run these meetings solo. I would bring in senior leadership as well. I’ll give you a quick story.

In 2009, I got a meeting with the head of talent at Intel. The COO of CareerBuilder hit me up and said, “Jake, I just heard the CEO of Intel speak. Go get me a meeting with the head of people.” So I call up the head of talent, and I say, “Hey, our COO just heard XYZ speak. We want to set some time up to talk about talent acquisition. It’s obviously important at Intel, etc.” And we got the meeting, and I was not equipped at 29 to run a meeting with the head of Global Talent Acquisition at Intel, but I could find the right people who were. 

So I’d do a lot of my own research. I would do my own planning and messaging. And then once I got into a certain level of conversation, and up there in the fortune 500 and 1000 space, I’d bring in people that were more senior than me to help me with those conversations. Use your internal team to move up the ladder. And this is true today, just as it is true in an up economy, just as much as in a down economy. But in a down economy, think about it. These executives are even busier, and they’re making really hard decisions. 

I’d have my team members come up to me and ask, “These companies just laid off a hundred people. How can we pitch them?” And it goes back to the mindset I talked about first. That these companies still need help. They might have had to make some tough decisions here, but they still have other parts of their business that must run and operate. And every company that’s doing layoffs is also hiring. Right. And that doesn’t make them irresponsible; they just have to refocus. So you have to train your team to have this mindset and to look for the areas of opportunity. Look for growth opportunities. No company says, “Hey, this happened; we’re going to go into a shell and not worry about the outside world.” They still have to run a business.

And now this goes back to what I said for number two, which is business conversations over product. If your team doesn’t have business acumen, you will be in a really, really hard place.

If we fast forward, I left CareerBuilder in 2010 to take over as a VP of Sales at Glassdoor. The economy was just starting to rebound. What we did very early on coming out of the downturn, was I used a very similar playbook, and we didn’t talk about the reviews. Instead, we talked about outcomes. “Hey, Cisco, I know you’re looking actively for software engineers like this. I had over 300,000 views on your page, and the number one job they’re interested in is a software engineer. We should have a conversation.”

One thing I learned early on from many great sales books was to talk about selling the vision and always think big picture. So for all of you in B2B sales who are worried right now and are thinking, “Hey, what’s next for me?” I want you to go back and think about this. How well do you know your customer? How well do you know what they do, how they live, their challenges, etc.? Because if you don’t have that, selling in a down economy will be very, very difficult. 

#6 Don’t get desperate

I have two more high levels here on being in B2B sales as the economic downturns, and then I actually will talk a little bit about how to get a job in a down economy because I know there could be some of you out there that are hurting here as well. 

But the first of these last two is don’t get desperate. Meaning the thing that I’ll see salespeople do in these types of conditions is once they start to worry that nobody needs what they do anymore, and they begin to panic and get desperate. 

Don’t just start to pitch more and more product and send more and more emails and proposals. If anything, I suggest you do less and less at higher quality. 

When the economy starts to go down, many people start doing more of the old thing because it’s familiar in an uncertain time, but the reality is the old thing never really worked well in the first place. So this is really an important one. Don’t get desperate.

#7 Hard pivot messaging 

My last piece of advice, and probably the most important, is to hard pivot messaging. 

If you don’t hard pivot your messaging, you will struggle. Instead, I mostly see people get really desperate, and they keep putting out more and more of the old messaging. 

One of my favorite stories during COVID was from TripActions and the CMO. TripActions was a travel management platform, and then the whole world went on lockdown. And so they got their SDRs, the head of marketing, and the head of sales in a room over the weekend around late March, and they rewrote over 30 plus sequences.

Instead of saying, “Oh man, we’re TripActions. We’re a travel management platform.” They realized quickly that nobody’s trying to buy a travel management platform right now. But what were they buying? TripActions came up with a concept and product set around trips and travel safety. So they started having preliminary conversations with people for the next month or two, product caught up, and then they were selling travel safety all of a sudden. 

All of you have a value prop that you can hard pivot to. So I’d really encourage all of you, in prep for a down economy, to start thinking about how can you change the way you pitch? 

For example, here would be my off-the-cuff brainstorm to hard pivot messaging.

I’m in the consumer package goods industry, and I sell into marketing specifically. I’d think about the trends and things consumers are dealing with right now, such as inflation, that’s also affecting my buyer’s (the marketer’s) goals. 

The cost of goods is skyrocketing. Well, what does that mean? If I’m selling to a premium brand, maybe consumers are thinking they’re too expensive. Perhaps they are buying generic alternatives instead. Maybe my job as a marketer is shifting to being more about why we’re premium or more education-based. So how can I pivot my messaging to that? I might reach out to that head of marketing and say, “Hey, we’re working with many other category leaders like Bandaid and Kleenex, and we’ve seen that with inflation, many of these products’ consumers are looking for alternatives. And marketers for premium brands like Kleenex are looking for new ways to do XYZ. And that’s what we help with.”

This is just an example, but I promise you if TripActions can pivot and find messaging that resonated in a world where nobody was traveling, and they were a travel management platform, all of you can hard pivot your messaging as well. 

That’s on the company side of thriving in b2b sales in an economic downturn. The last thing I want to cover is for individual salespeople looking to thrive in B2B sales in an economic downturn.

Bonus: Searching for work in a down economy

In times like these, I see many people get nervous and leave. I’m telling you, being with a company and getting to the other side of an economic downturn, you’re going to see the good, the bad, the ugly, and the amazing. 

So if you do have a choice, and I’m not saying you should absolutely stay put, as there’s probably are some sectors where the word run is, is applicable. But for many of you, I would think, are you running because it’s getting hard, or am I running because it’s helpless? 

And like I said, the first thing I had here was mindset. If you’re an individual, the same concept applies, and you just need to find the hard pivot, and you can find a way to transition your messaging. 

But say you do need to find a new job. If I was getting laid off or just got laid off, what would I do to stand out? What would I do to get a job? Because, as I said at the very beginning, people are still hiring. If you’re in tech sales and you were just laid off, I promise you many, many, many companies are still looking for people. 

The interesting part is that it’s a lot of the advice I gave in the first half of this session. You have to do more to stand out. This time it’s just a different buyer, and the buyer is your potential employer.

What’s going to start to happen to hiring managers over the next three or six months is that they are going to get inundated with resumes. 

I’ll go back to the story in 2006 when I joined CareerBuilder. I had joined multiple organizations and moved up quickly. But as I was transitioning into tech, I knew that it’d be difficult to start where I was. And so I took a more lateral move even though I’m not a big fan of too many lateral moves. But for many people, if you just got laid off, or if you’re thinking about changing jobs, understand it’s going to be more difficult to get the rapid increase in salary or that dream job. You’ll have to start lower and move up, but it’s still possible.

You just need to know your customer, and your customer, in this case, is a hiring manager. Don’t be lazy if you’re just submitting an application or sending a message to the hiring manager. I get some pretty lazy messages on LinkedIn. 

“Hey, Jake. I saw your hiring for this role would be great to see if I’m a fit.” My first thought is now I’m expected to go and look at your profile, and I’m supposed to go and do the homework now for you. No. If I think the message is clever enough, I’ll introduce you to somebody, but you have to do a little of the work and research.

Many people struggle with this because it’s just like sales. You might research and reach out to ten hiring managers, but only two of them respond, and you ask yourself, why did I do all that work?

Well, don’t you do that exact same work in sales every day?

First, really think through the types of industries that get you excited. And then you have to take my exact same advice from before and get to know your customer, which in this case is the hiring manager.

For example, this message could look like, “Hey, I know right now that you all may be starting a hiring freeze (or I saw on LinkedIn, this and this with that said), but I know many organizations like yours are still looking for A-Level talent. I am A-Level talent. And here are the top three ways I will be able to help and support you. Let me know if you’d at least be up for a 20-minute introduction call.” 

That’s it. I’m telling you, the percentage of people that do any amount of research before they blindly reach out is like 2%. Instead of just taking five minutes to send a message, you’ll have to take 15 or 20 and be more thoughtful to stand out. Because if you’re a B2B seller right now, and you just got laid off, to get a job by just applying online, it’s probably not going to happen for you. 

I know it’s tough. I’ve been fired before as well. Especially if it’s your first time getting fired, you’re like this is the worst. I can tell you, though, that you will get through it. It will all work out. And when these things happen, you just have to lean in a little bit more. 

Wrapping Up

I hope this helps a lot of you out there. This is a cycle. I’ve now seen it through the 2000s, in COVID, and again if we do end up going into more of a dip.

If you want to thrive, not just survive, but thrive, just do these seven things. I’m telling you this from my personal experiences. This is what I did.

I’m not an economist. I don’t know what’s going to happen with the economy. But the good part is, if you get really good at these things, they will make you an even better seller even if the economy never goes south. 

So hope this helps some people out there, good catching up. We’re going to be doing LinkedIn Lives pretty consistently going forward, and you’ll start to see more of these topics from me at least once every two weeks.

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