How to close $50k+ deals

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The Most Common Route to $50K+ Deals for Medium-Sized Newsletters

Want to close five-figure deals, but you’re stuck scrapping after pennies? This one is for you.

Here's the actual path to $50K+ campaigns that most newsletter operators miss.

❤️ Large Deals Come From Renewals

The largest new business deal I've closed in many years of selling newsletters is $40k Trust me, the big deals (in newsletter land) come from renewals, not cold outreach to enterprise brands.

If your average primary is under $5,000, your first step isn't pitching bigger packages. It's getting perfect-fit advertisers in the door and turning them into long-term partners.

Fortunately, and unfortunately, newsletters do fall under performance budgets 99% of the time. So don’t fight that. The unlock to sexy budgets is hitting marketing KPIs.

🐣 Start Small But Smart

Don't worry if initial deals are small. Ideally, you don't want standalone placements, push for 3+ touchpoints in every package to build familiarity, test different copy angles and get performance.

That said, don't turn down single placements either. If they perform well (and they absolutely can), you're laughing. Just make sure you position the single poke as a test early on.

The key is qualifying hard upfront. A $2,000 test with a perfect-fit brand is more valuable than a $10,000 one-off with a misaligned advertiser who'll never renew.

🎁 Over-Deliver on Every Campaign

Not all audiences are created equal. This will be easier for some newsletters, harder for others. But you're better off underselling and over-delivering long-term, even if it affects margins or doesn’t optimise revenue in the first instance.

Set conservative expectations with the data you have, then (try to) exceed them. If you promise 5,000 clicks, deliver 6,200. If you estimate $35 CAC, hit $28. You can do this in a low-lift way, like giving away tertiary single sentence placements to give it extra juice.

Over-delivery, obviously, will help the data-backed decision of renewing, but it also creates emotional equity. Brands remember how you made them feel, not just the numbers you delivered. They’ll appreciate the extra mile (or kilometre)

Also, don’t be too hard on yourself when campaigns don’t cream. Campaign performance is not fully in your control. It’s one third in your control (I’d say), a third down to the brand, and the final third is just luck.

🫡 Get Good Reporting Processes

For great fit brands or large campaigns, put a campaign wrap-up call in the diary as the campaign starts. Create a report, PDF, Notion doc, whatever format works. This should contain results, campaign analysis, your insights, and opportunities for future collaboration.

This creates a genuine conversation around "What are we going to do next time?" rather than "Should we do this again?"

Assuming they're a great-fit brand and the campaign performed average or above, you should be able to convert this into at least a renewal opportunity, if not an immediate deal that retires your mum.

The wrap-up call is where small deals become medium deals, and medium deals become large deals. Don't skip this step.

❤️ Act Like a Campaign Planner

To build trust and land large campaigns, you need to act like a consultant. During pitching or campaign planning calls, you should be listening and asking questions 70-80% of the time.

Understand their goals, target market, decision-making process, budget cycles, and what success looks like internally. What worked in previous campaigns? What failed? What's keeping them from hitting their growth targets?

The actual talking only comes when you fully understand what the brand needs. Then you propose specific solutions: what dates, what format, what success metrics, what the decision-making timeline looks like.

This approach positions you as a strategic partner, not another media vendor sending generic proposals. Strategic partners get larger budgets and longer commitments.

🤺 Quickfire Closing Tactics

Spread out payment terms - It’s fairly common to have split payment terms on deals above ~$30k. It’s for them to manage their risk. And it’s fair.

Cancellation clauses (use sparingly) - "If we don't hit [metric] in the first 30 days, you can cancel the remaining campaign" reduces perceived risk for first-time large commitments. I don’t like this, for obvious reasons, but have seen them be included to help the deal get over the line. Just be smart about it.

Added value - Bonus placements, these cost you little but increase perceived package value significantly. You can always blend the ‘lost’ cost into the package so you're well above your floor pricing anyway.

Bring in other channels - If you have podcasts, YouTube, events, or other properties, bundle them to create comprehensive campaigns that justify larger budgets.

Get creative within the newsletter - If you don't have other channels, offer founder interviews, dedicated sends, linked video content, gated resources, or custom editorial features that differentiate your offering.

P.S. Need help selling those BIG DEALS? My agency Ad Sales as a Service helps new media companies do just that.