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Last week, a founder in one of the private CEO communities I’m in posted a question that shows up there every couple of months: does anyone have an SDR agency they actually like?

Crickets, mostly.

That got me curious, so I went back and read every thread on outsourced SDRs in that group since 2024. Dozens of asks. Lots of recommendations. And when you look at who’s doing the recommending, a big chunk of them own the agency they’re recommending.

Compare that to firsthand wins from people with nothing to sell — you can count them on two hands.

One founder in those threads was refreshingly honest about what happened when he outsourced appointment setting:

That’s less than one deal a week. Meanwhile, the leads that came in through his newsletter and webinars closed around 75% of the time (insanely good, btw).

And it’s not just one guy. When SaaStr surveyed 1,200+ founders and sales leaders, only 7% said they’d really gotten outsourced SDRs to work. Another 26% said it “sort of” worked.

So about two-thirds tried it and it just didn’t work.

The agency usually isn’t the problem; more so, the problem is what you hand them.

An SDR agency scales a message. If you haven’t proven the message works, you’re paying someone to scale something that doesn’t convert, faster, and with your name on it.

Pete Kazanjy, who literally wrote the book on founder-led sales, has a bar I like: don’t hand off sales until you’re winning roughly 15 to 25% of deals and have 10 to 20 customers who’ll vouch for you. Before that, nobody knows what to tell the reps to say. Not you, and definitely not a vendor juggling a dozen other clients.

Paul Graham has been saying a version of this since 2013: early on, founders have to go get customers themselves. An outsourced SDR is often a founder paying someone so they can skip that part.

I’m not anti-outsourcing. When I was CEO of Hampton, I outsourced frequently.

When we had more inbound demand than our closers could handle, we brought on contract closers (not an agency, but highly vetted freelancers I found myself). Our close rate was sitting around 40%, which was miles from the under 10% benchmark above. We were crushing it, so I knew our playbook worked.

Simply put, I wasn’t handing anyone a puzzle, I was handing them a recipe.

And this wasn’t about finding cheap labor (not that cheaper labor can’t work). We just needed more capacity. And the contractors had a sales lead who trained and managed them, and they sat right next to our full-timers.

Someone that reported directly to me, owned the outcome.

Here’s roughly how the rest of the company shook out in the early years:

Geoffrey Moore has a line for this: outsource the context, in-source the core. The stuff customers pick you for stays inside. Everything else is fair game.

The SDR question is really one version of a question every founder hits over and over: who should actually do this work?

I’ve circled this a couple of times in past newsletters.

In May, I wrote that before any hire, you should ask whether the work could be solved another way. And more recently than that, I’ve said that fractional usually gets you fractional outcomes.

So here’s the actual map I use myself:

Some providers blur these lines, and that’s fine. These are operating distinctions, not rigid boxes.

I run every “we need help with X” through these, in this order:

The truth is that every model on that list can work, but they also all fail in a generally similar way: you use them to avoid making a hard decision, you use them without deciding who owns what, or you use them without proper support and guidance.

So pick the work and the accountability first. Pick the employment model second.

“We need a VP” is often a very expensive way of saying “we haven’t diagnosed the problem.” “We need an SDR agency” is usually a slightly cheaper way of saying the same thing.

Paul Graham shared his favorite office-hours question: instead of asking how a company can make more money, ask what would make it more powerful. The money question almost always leads to tweak this, tweak that, which is fine sometimes, but the power question (own the customer relationship, get the money flowing through you, add network effects) is how you think big instead of small.

Run it on your own business this week. It’s harder to answer than it sounds.

Juliette Ryan makes a sharp case that for 3,000 years, good writing was evidence someone had actually done the thinking, and AI broke that signal. The scary part isn’t people faking it. It’s people who prompt their way to a polished essay and genuinely believe they understand what they published, which is basically this week’s Signal applied to your own brain.

Shane Gillis and Danny McBride play rival weathermen in a four-minute Kalshi ad McBride wrote, and it’s absolutely hysterical. I hate what betting is doing to young people, so I wish it were an add for literally anything else, but you gotta respect them for handing two comedians the keys and let their POV run the show. More creative people with a real voice deciding what marketing looks like, better for everyone.

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Hope everyone has a great weekend.

And until next time, thanks for reading.

Jordan