I raised $180 million and hated the ads too

This time of year, I love living in Cabo.

Not just because it’s cooling off into 65-degree winters, but because I’m out of range of the political ads.

Election Day is Tuesday. If you’re in the States, you’ve been buried in them for two months, and there are a couple of days left to go.

I spent about 16 years in political fundraising at the U.S. Chamber of Commerce, which most people don’t realize is the biggest lobbying spender in the country. I started there as a sales rep and left as Managing Director of the entire small and midsize business division: phone sales, field sales, direct mail, and digital, nationwide.

I even wore a tie from time to time.

Over that stretch, my teams and I raised about $180 million for advocacy and elections. Everything from $100 contributions over the phone to six- and seven-figure asks in Fortune 500 boardrooms.

So, you could say I know a thing or two about sales and marketing in the political space.

Before we go any further: this has nothing to do with which side of the aisle you sit on. I don’t care, and it doesn’t matter for what follows.

I got into politics because I was passionate about it. I wanted to make a difference. Sales was just my way in. The plan was to sell long enough to get a law degree and become a lobbyist.

Sixteen years later, I left passionate about sales and less passionate about politics. That has nothing to do with the Chamber, which is an incredible organization I’m proud to have come up in. But watch how the sausage gets made long enough and it’s easy to lose the thing that got you in the door. So, I moved on.

I took the lessons with me, though. And that brings me back to the ads.

We all hate them. Or we think we do.

Then why do they run them? Why are campaigns and the groups behind them on track to spend a record $11.6 billion on political ads this cycle — more than was spent in the 2024 presidential cycle?

Because they work. No, not every single ad works, and not on everyone. But the people buying them run boatloads of research, test and measure, and keep buying what works. Nobody spends $11.6 billion on a hunch.

For the sake of argument, set the annoying part aside. Behind the attack ads, the texts you never signed up for, and everything else you despise about campaign season, there’s a playbook that will sell more of whatever you sell.

Here are five pieces of it I still use today.

Political campaigns aren’t targeting “Republicans” or “Democrats.” Every ad and every mail piece is built for a narrow slice of the electorate.

I know. The texts you’re getting from both parties don’t feel targeted or smart. But you’re getting them from both sides because the data says you’re worth texting. Most of you own a business, vote every time the polls open, and have given to somebody at some point. Give once and your name gets passed around until every committee in the country has it.

Texts are also the cheapest thing a campaign sends, so they go out in bulk. The money and the research go into the TV spot and the mail pieces, which are built off a voter file with hundreds of data points on you, tested with polling, and cut in multiple versions. You see the version aimed at your slice.

The targeting is less “Republican” and more “Republican-leaning owner of a 40-person business in a swing district who’s worried about what the next tax bill does to his margins.” The message that moves him is a different message than the one that moves a suburban mom in the same district who’s worried about schools, even if they vote for the same candidate.

For your business, the bare minimum is the R-or-D level: an industry or vertical. Law firms. Dental practices. Manufacturers. Engineers.

That’s a start.

If you want the message to land, go a few layers deeper. Law firms with 25 to 100 users, no internal IT, a managing partner who makes the call, a cyber insurance renewal coming up, and a headcount that’s grown over the last year.

Now you can write something that reads like it was written for that person, because it was.

Whether I was asking a small business owner for $1,000 or a Fortune 1000 company for $100,000, there was always a person on the other end of the ask.

The better I understood that person — what they cared about, what they were afraid of, what they wanted to be true a year from now — the more likely I was to get the outcome I wanted.

It’s no different in B2B sales. We talk about companies like they make decisions. They don’t. Somewhere inside every organization there’s a person, or a handful of people, making the decision on the organization’s behalf. And every one of them has their own pains, motivations, and outcomes they want.

The owner wants fewer headaches, happier employees, and growth. The VP of Ops wants less risk, lower costs, and to look good to the owner. The office manager wants the complaints to stop landing on her desk.

The job of marketing and sales is to figure out which of those people you’re talking to and speak to what they want. The more accurate you are, the better your conversion.

A small business owner can write a $500 check just to make a statement about how he feels. The emotion there is easy to see.

The $25,000 that goes through board approval at a mid-size company, or the $1,000,000 a public company commits? That looks like a business transaction. It’s still emotion. It’s just emotion that had to survive a committee: fear of what a regulation does to the margins, or wanting a seat at the table when the rules get written.

Every B2B sale you make works the same way.

If you sell IT services, it’s easy to treat the deal as a logical fix for a logical problem: network issues, security risk, compliance gaps. But I promise you there’s an emotion under that logic.

The owner who “just wants a reliable help desk” is tired of being the help desk. Every time Outlook goes down, somebody walks into his office. He’s buying his afternoons back.

The CFO asking about backups read about the company two towns over that paid a six-figure ransom and still lost a week. The question is about backups. The motivation is fear.

And the ops VP asking about compliance is already picturing the board meeting where he has to explain the audit findings. He’s buying so that meeting never happens.

Find the feeling under the logic and speak to it. Your conversion rate will follow.

One thing we almost never talked about when raising money in politics? Exactly what we were going to do with it.

The pitch was “we’re raising X million to win this fight.” We didn’t talk about features. We talked about outcomes.

As I tell sellers in training all the time, people care far more about the transformation you can deliver than the mechanism you use to deliver it.

So, whatever you sell, you’ll do better marketing and selling the outcome than the tools, tactics, and techniques it takes to get there. For my IT friends, that means the tech stack goes in the appendix. What goes in the pitch is what the business gets: fewer interruptions, a security posture they can show the insurance carrier, an audit that comes back clean, and an owner who never has to think about IT again.

Political fundraising comes with urgency built in: there’s an election date. Everyone knows it, everyone accepts it, and using it is completely fair game, because it’s real.

That date creates an enormous amount of motivation, and I have years of data to prove it. As the deadline got closer, close rates went up, and so did revenue per sale.

In B2B sales, nobody hands you a universal cutoff date like the election. You have to find the deadline, or build one.

The best version already exists in your prospect’s world. Their contract with the current provider ends in March. Cyber insurance renews in January and the carrier wants MFA on everything. The audit is in Q2. They’re moving offices in 60 days. The fiscal year ends in December and the budget doesn’t roll over. Those are election dates. They’re real, everyone involved knows them, and tying your proposal to them is exactly what a good campaign would do.

The second version you build yourself. Proposals that expire in 30 days. Pricing that goes up January 1 because your vendor costs did. A start date tied to when your onboarding team actually has an opening. Basically a campaign with a cutoff.

One rule that’s got to hold (and it’s the reason the Election Day deadline works): it has to be true. If the quote expires, let it expire. If you have two onboarding slots this month, don’t suddenly find a third. The minute a prospect catches you faking a deadline, you’ve lost the one thing that makes deadlines work: everyone believes them.

Those are five of the lessons I carried out of politics. There were more, but these are the five I watch B2B sales teams skip most often.

By Wednesday morning, the ads will be gone, the texts will stop, and most people will go back to insisting none of it worked on them. Enough of it did. That’s why there’s $11.6 billion behind it.

You don’t have to like it. But the most tested, most measured sales operation in the country has concluded that the sale happens when the right person feels something, sees the outcome, and has a date. A lot of B2B sales processes still open with the tech stack and close with “let me know if you have any questions.”

Pick one of the five and fix it this week.

Adios,

Ray