How to get on track in 2025

There’s mostly two types of founders I’m meeting lately.

Those who are upset at themselves for not doing everything possible to hit their goals in 2024.

And those who are blaming everything but themselves for not hitting their goals in 2024.

For the first founder, they took time over the holidays to recalibrate. And on Jan 2, they increased the intensity at which they do sales by 5x.

The second founder, I’m noticing they’re easing their way into 2025. They only started to plan for the new year after the new year. They are “getting ready” do to more sales. They’re list building, updating their website, writing landing page copy. And on Jan 17, they still haven’t really taken proactive action to get sales started.

I can tell you that the first founder will have an amazing 2025.

The second founder has about 2 weeks to bust out of their funk, or they’ll have a similar year than the last.

In this newsletter, I’m going to go through the topics, questions, and thoughts I’ve heard the most so far in 2025 to help you get on track quickly.

Table of Contents

• Forget capacity

• Sales math

• Prospecting and targeting

• Fear of being salesy

• You can’t win early, but you can lose early

Forget capacity

I’m going to address this one first, because I’ve heard it 3 times in the last week.

Don’t pre-maturely kill your momentum.

It is really hard to get sales and revenue going.

And I’ve come across founders who want to take a break on sales because they feel like they might reach capacity.

Not that they’ve exceeded capacity.

But the idea that “if all these deals close, I won’t have time to service them.”

First, if you end up exceeding capacity, that’s a good thing. Means you’re selling faster than you’re shipping. Great indication that it’s a problem space worth pursuing.

Second, those deals in your pipeline, 10-20% of them will close. Not 100%. So all of this fear of being overwhelmed by future business, likely won’t happen. You’ll likely be under capacity, by quite a lot.

None of these deals have closed. And until you have a signed contract and scheduled the onboardings, you do not want to lay off the gas.

You can always stagger the onboardings if you do close more than expected. And if you are really exceeding capacity, then you should look to delegate non-sales-related stuff.

Because this would show you have momentum, and the market is hot.

Most startups have a limited window of opportunity. A prospect has a pain that needs to be solved now. If you’re there to help, you win the business. If not, someone else wins the business.

You have tons of competitors that have way bigger teams and marketing budgets than you, they’re not slowing down.

There are also tons of startups launching every day. They’re not slowing down.

The fear of hitting capacity needs to exit your mind. And sales should be the last thing that takes a break if capacity is hit.

Revenue is oxygen, and you don’t want to run out of breath.

Sales math

Take time to do some basic napkin math so you understand at what intensity you need to operate.

If you’re looking to land 10 customers, then how many proposals do you need to send? How many demos do you need to do? How many intro calls do you need to have? How many prospect convos need to happen to book those calls? How many outreaches do you need to generate those convos?

Then take a look at what timeframe you want to set for your next milestone. 90 days? Divide all of these sketched out numbers by 12 weeks, and it will give you your weekly pace.

Then go back and fix your math - there’s lead up time from prospecting to meeting booked. And then there’s sales cycle times from intro call to close. So depending on how long it takes to run a sales cycle, you need to discount your timeframe by this. So that 12 weeks might be a really intense 6 weeks of prospecting so you have enough time to get intro calls to close. There’s always a lag/delay from action to results (also another reason not to worry too much about hitting capacity).

So do your sales math, then compare what you’re doing today to what the math tells you to do.

I have a client of mine that dabbled into outreach last year. Closed a couple consulting deals and free pilots. The intensity wasn’t really there.

So we did the math. They want to close $30k in consulting contracts by end of March. My client has a pretty large network that they hadn’t tapped into. So we decided to focus on referral prospecting.

They needed 20 meetings 1st week of March to hit his goal. They prospected for 7 days and generated 10 meetings, only going through half their network.

This did two things for them:

1. They realized that they could significantly crank up the intensity, which they didn’t do in 2024.

2. They realized that thinking in timeframes could hold them back. They were setting arbitrary timeframes. This shifted their thinking to “How fast can I generate $30k,” or “what does it take to generate $30k.”

They’re pacing way ahead in the 3rd week of January already. I told them they might be sandbagging their goals a bit, which made them chuckle.

But without doing the basic math, you really don’t know. And if the math seems easy, then crank up the intensity so that it’s hard. Sales should not be easy.

Prospecting and targeting

If you have a large list of target accounts, you’re not prospecting right.

If you’re sending 1000s of emails to a generic list, this isn’t outbound prospecting, it’s email marketing.

Success rates of email marketing are fairly low. You can do it, but lower your expectations for what you’ll get.

Prospecting requires you to find companies and contacts that have pain you can solve. That pain should be specific and precise.

Which means that your list will be small.

And your list should help you easily craft a personalized message in seconds/minutes.

When you’re targeting, you have to reverse your way into filters, not start with filters.

The way you do this is through a basic positioning framework (available in my FOUNDER Operating System playbook, modified from April Dunford’s Obviously Awesome book.)

1. List off the alternatives your prospects are using to currently solve the problem. Think in alternatives, not just direct competitors. Most folks use spreadsheets, docs, and manual labour to solve stuff.

2. List off all the ways you’re DIFFERENT than the alternative. NOT BETTER. I see so many founders say how much better their product is. That’s not for you to decide. Better is subjective. So list off what’s different.

3. List off all of the pains those differentiators solve, and the value that comes from solving that pain.

4. Then reverse your way into companies and people that would have the characteristics of this pain and that would REALLY really care about the value of your differentiators.

Number 4 is how you end up getting a shortlist of traits for your targeting.

Then you start going through how could you filter on some of those. You can use LinkedIn Sales Nav, website scrapers, Clay, Apollo, whatever you have access to.

You won’t get it down to a perfect list, but it will be more targeted.

Then you’ll have to do the hard work of going through each account and qualifying for the stuff that can’t be filtered on.

For example, on of the things I look for when prospecting founders is whether or not that have customer logos/case studies on their website. If I see a solo founder, with a startup that’s less than two years, and no logos on their website, I can make a fairly accurate assumption that they’re struggling with founder-led sales. I can find solo founders with startups less than 2 years old through LI sales nav. I can also filter for technical founders (which are even better for me) by looking at past job titles, making sure they don’t include sales or marketing and are more dev/eng/product focused. But I still need to take the extra step to go check logos on website.

But when I do this, the messaging writes itself. It could be something like:

“Hey Donna - noticed you’ve been at it solo with Acme corp for a couple years, but no customer logos on your website yet. Makes me wonder if you’re struggling with sales?”

If I send a LI DM like this, and they are struggling, it’s easy for them to answer. Then I have a quick convo, move them to a free coaching call, some convert, the ones who don’t get some value/help from me.

Fear of being salesy

Nobody likes a salesy sales person. We’ve all encountered this. Walk into a retail store and some overly-eager salesperson runs up listing off all the discounts. You immediately push back and say “I’m just looking” even though they could probably help you find whatever you’re looking for much faster.

Here’s the thing, you can never force anyone to buy something.

And in B2B sales, the person buying is likely not making the decision on their own (unless you sell directly to solo founders).

They have a pain. Others need to agree that the pain is large enough to prioritize. Then the group needs to agree on possible solutions. Then they need to agree on the best solution for them. Then they are spending the company’s money to solve it.

So B2B purchases are significantly more complex than B2C purchases.

And pressure tactics never work.

But what does work is helping them buy. Ideally that leads to them buying your solution, but sometimes that’s not the case.

As much as it’s hard to do sales, it’s hard to be a buyer. AI is accelerating tech at a pace that’s never been seen. There are hundreds of options to choose from, at all sorts of price points. And it’s really confusing to figure what’s best when all of the software out there looks the same.

You don’t want to get it wrong as a buyer, because that would look bad on you and potentially put your job at risk. CFOs are always putting pressure on reducing budgets. So sometimes, the easiest thing to do is to do nothing. Just live with the pain. Because buying is suddenly more painful.

You can work with all of this. Not in a manipulative way, but in a helpful way.

Find out if they have a problem. Ask them what they’ve done about it. Ask if they’re open on learning about a new way of solving it. If your product is actually helpful to them, they’ll enter a sales cycle.

The other thing about fear of being salesy is how you prospect. I have clients that have swung the pendulum a bit too far. In an attempt to “not come across as salesy” in their prospecting efforts, they’ve gone too far the other way and are talking about nothing. Which ends up on the receiving end being even more annoying than being pitched.

Good communication is specific and direct. Don’t dance around what you’re trying to do with prospecting, because that comes across as not being transparent. It’s the exact opposite of what you’re trying to accomplish.

Target folks who likely have the pain. Be direct with them about why you’re reaching out to them specifically. And ask pain-based questions.

You’ll still get rejection - that’s part of sales, won’t ever go away. But you’ll get folks who are having convos with you. And instead of these convos being “how’s 2025 going for you?” - they’ll be about something relevant for both yourself and the prospect. Less time wasted on both sides, which is always appreciated.

You can’t win early, but you can lose early

I’m going to leave you with this.

When I was VP Sales, we had an annual sales kickoff at an offsite. Part of those sales kickoffs included some sort of motivational speaker.

Now, we were a startup with no budget, so the motivational speakers were always youtube videos, but it did the trick.

We watched something about long-distance both races. The kinds that go across 100+ days.

A team would have to live together on a boat, and constantly be in sync.

And there was a quote from this that stuck with me for years.

“You can’t win the race early, but you can lose it early.”

They were referencing about making bad decisions at the start. Slacking, going too hard, not having a plan for pacing. If you tip your boat on day one, you’re done. If you break your sail, you need to spend days fixing it, you’re done. There’s no recovering from that.

You can’t win the race early.

But the actions you take now will have a big impact of where you land on Dec 31.

If you decide to slow roll your way into the new year, you’ll be outcompeted.

If you decide to take a break with sales because if everything goes well you might hit capacity, you’re going to lose your window of opportunity.

If you decide to send 5 outreaches a day instead of the 50 your sales math is telling you to do, you will miss.

The actions you take today. Tomorrow. Next week.

They’ll all set the pace for the rest of the year.

January is generally a slow month in sales. But building the mindset and habits for it now is what’s important.

If you haven’t gotten started yet, start now.

Let me know what you think of the newsletter, or what topics you’d like me to cover. Always appreciate hearing from you :)

For more practical early-stage sales tips, connect with me on LinkedIn.

If you’re looking for help busting through mindset and getting specific with sales tactics, reach out for coaching packages.