Dear SaaStr: Is It Normal to Feel Like a Pest When Prospecting for Customers For a Startup?

Dear SaaStr: Is It Normal to Feel Like a Pest When Prospecting for Customers For a Startup?

Yes. Most of us will feel like a pest when we start doing outbound. So … get better at it, get over it, and hire folks who know how to do it.

**Sales is hard. **It’s being told No a lot. It’s having literal, or virtual, doors shut on your face.

Sales in part is figuring out how not to be a pest. Yet still be a pest.

It actually doesn’t get that much easier over time, either. Yes, once you have a brand, and inbound leads, the engine gets more established. But then you raise the quotas, and sales is still hard. And then, the easy accounts are already in play for the SDRs. So outbound gets harder, too, later often.

So first, find great salespeople. People that can push through all the NOs. That can make prospects love them, and your product. Also the best outbound sales folks and the best AEs and VPs know how to mostly not cross the line to pest. Sometimes they still cross the line. But the best ones know the playbook and knowgenerallynot to cross it. Because it doesn’t get them the sale. You need to be a bit of a nudge to be good in sales — but not a constant nudger. The line is fine 🙂**And second, value them.**The best ones are worth so, so much. Don’t overpay them as a % of the revenue they bring in. But if they bring in a ton — make sure they make a ton.And third, give them a career path. All those NOs? One incentive to push through is the chance for a promotion.And fourth, treat outbound as a science and an art. One to get better and better at. Do endless generic emails work? Not really. Does a perfectly tailored outbound email work, at just the right time? Sometimes. Yes, sometimes. Often enough that once you finally see it work once, go find another 10 prospects just like them. And write them the world’s best pitch, customized for each.And get rid of mediocre salespeople. It’s just too hard for folks that can’t take 99 NOs. And turn the 100th into a Yes. If they can’t close, if you smell too much fear, if they give you 99 excuses why they can’t close a deal — move on. Maybe you can carry some mediocre sales reps later, at scale, once you have a strong head of sales. Someone has to be mid-pack after all, by definition. But move on from any that can’t do it, at least until you have a head of sales you trust.

Outbound is tough. Done wrong, it just annoys people. Done right, it always works. Yes, even in 2026.

If you have any paying customers at all, there are 10 more just like them. Go find them. Share the story of why the first one picked you. And get a meeting.