These days, it can really feel like the Old Bag of Sales Tricks is starting to just not work anymore:
- With maybe 500x the SaaS vendors of 10 years ago, there’s so much noise.
- Emails get blocked, spam filtered.
- AI SDRs seem to be only adding to the noise,
- No one picks up the phone or even has voice mail anymore.
- 50 calls a day feels awfully dated.
- Everyone gets 10,000 drip email campaigns sent to them.
Are there categories where outbound sales just doesn’t work? Well maybe, but let’s step back a minute.
One thing has not changed in SaaS in the last 15 years:
- Everyone spends 1-10 hours a day in email. Even more these days as we are glued to our devices, phones and computers.
And
- Everyone needs solutions to their top 1 or 2 biggest problems. Everyone. Problems 3-300 maybe can wait, even if you don’t want them to. But every business leader has a few top pressing problems that a software vendor can solve.
But:
- The 10,000th uncustomized mass “i came across you in my research” or “time for coffee?” email is just not going to work, at least not 99 times out of 100. A very few folks are actually good at this. But almost everyone just goes through mass campaign motions here, with very little yield and lots of prospect burn out.
But if you know your prospects and their problems, and target them exactly, and hit them when they’re looking for a solution — outbound sort of always works. At least some of the time.
At least, it almost always creates a dialogue some of the time. You might not win the deal, but if you really try to solve 100 prospects’ #1 problem, more than a few will open the emails, and a few will likely take the Zoom.
Given that, realize if your outbound sales team isn’t performing at all, maybe it’s not your app, or the competition, or the market, or that there are too many vendors in the space. It’s their approach.

The old sales playbooks of 2009-2023 may not work as well in 2025 and 2026. But VPs are still sitting on their computers, struggling to hit their plans, manage their teams, hire the next great engineer, deploy their software releases, and hit their number. And buyers are still mostly humans ;), in many cases, sitting in front of their computers or at least their phones.
If you have one of 10,000 tools in the market that all sort of do the same simple thing and you can’t describe your 10x feature — well, then yes, perhaps outbound won’t work.
But if you have a solution to a true, real and important headache … especially at bigger customers and/or with buyers that have the time to do at least a tiny bit of discovery …
Well, then iterate and find a way to get to the VPs, Directors, and CEOs whose very top headaches and problem you can truly solve. Slow it down. “ABM it”. Write 10 custom emails a day, that you research, and really show how you can help. Instead of 100-1000 automated cadences.
They’ll answer that email. And do it right, and email is magical. Even the busiest CEOs still open it.

Hey Jason, this is a great article. I think also reassuring for many entrepreneurs out there doing saas. Question, do you see the need to have more of an account based marketing, or targeted approach to your outbound strategy? What I mean is, does there need to be more personalization and timing with your outbound strategy? If so, it sounds like that would diminish the quantity but increase the quality. With Enterprise saas, I’ve seen that we have to really understand the customer and create Target list and overtime learn the specific needs of those targets. What do you think are the best ways to apply outbound to Target list? You don’t need to answer this here, but it may be a future topic for a post. Regards!
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