Dear SaaStr: I’ve Been Out of Sales For 6+ Years. Is It Too Late to Get Back In?

Dear SaaStr: I’ve Been Out of Sales For 6+ Years. Is It Too Late to Get Back In? I stayed at home as a parent and then played professional poker for several years.

Ok here’s the thing: you have 2 flags already (and staying home for the kids

isn’tone of them).** Issue #1 isn’t that you stayed home for a bit for your kids (almost everyone wants to be supportive here) or even that you played poker per se. But it’s that you’ve been out of the game for 6+ years in sales and doing something else for work.**

**Second, working from home is a thing now for sure but **leading with that also says you don’t really want to hustle.

These IMHO are 2 tough strikes against you. It may not be fair or right but it’s just reality.

So — turn it around. Address them, don’t make a huge deal of it. My advice:

Be clear you want to get back into sales and will work your arse off. Don’t just act. Make it crystal clear you are a hustler. Follow up to each email in minutes. Not the next day. Share a bunch of thoughts on what you’d do your first week. Listen to some webinars. Do 10x the diligence on each job you apply to of someone with a more standard trajectory. Spend 20 minutes researching each role and write the best email cover letter ever. You will stand out from 98% of applicants just doing this. Ask folks who know you are great for intros and referrals. Every startup CEO will take a meeting that someone that respect says was “one of the best they’ve ever worked with”. Even if it’s been a few years. If you aren’t willing to leave home or travel for sales, well that’s part of a lot of sales jobs. Not all but a lot of them. So be thoughtful and seek out companies that by their nature don’t require it at all.

It’s harder to stand out if you have an imperfect resume.

But you know what’s actually easier today? To stand out if you really, really go the extra yard and really want to work a true 40-50 hours a week. For real.