The persistent, software-enabled recruiter

by Randy Gingeleski

6 minutes to read

Persistent recruiters might just be software automation.

Post featured image

Recently a series of emails from a persistent recruiter struck me as authentic and impressive. Then, I found software (Amplemarket) to achieve the effect.

From the moment I joined a well-regarded application security group in 2017, recruiters have been trying to contact me left and right. There are probably two or more attempts per day but I’ve taken measures to block or hide most of this.
Phone calls are the worst.

Recruiter cold message collage

Maybe it’s unwise of me to say this but… if someone sends me a traditional email, it’ll almost certainly reach me. It’s just one avenue where the inflow of recruiting messages is so meager I haven’t tended to it.

Which brings me to this post on increasingly sophisticated sales and recruiting email techniques. 😉

After becoming more aware of such techniques, they now just strike me as insidious. Formulaic, “clickbait” titles hit me the same way. But maybe it’s just me.

Anyway, within the last couple months I got a “cold email” from a recruiter we’ll call Alex. The vehicle was not surprising… you can locate a working email for me off LinkedIn or GitHub. Straightforward enough.

The initial message is reproduced below with some redactions.

Date: Thursday 10/03/2019 @ 07:56 PM

Subject: Ready to Lead? // Product Security

Hi Randy,

I hope all is well. Sorry to message you out of the blue. I am not sure how things are going at EY but I wanted to share some information and see if you'd be open to a brief introduction. I recently partnered with a company named {{Companyname}}, a {{description for the company here}}. They are growing quickly and {{additional statements here to build credibility for unknown startup}}.

They are looking for someone with {{description for a security person written by a non-technical, not-security person here}}. If this sounds like something you'd be interested in exploring please let me know.

Do you have a couple of minutes to connect tomorrow? I am open tomorrow at 2pm if that helps. :)

{{Alex Lastname}}

With the aforementioned volume of these reachouts I get, plus my own busy schedule, plus the very low priority I place on these messages – not looking to change jobs – they’re something I ignore.

So that’s what happened. I ignored this email. A couple days later, though, a follow-up appeared.

Date: Sunday 10/06/2019 @ 01:51 PM

Subject: Re: Ready to Lead? // Product Security

Hey Randy,

Just checking in to my previous email. Does a Lead Product Security role at a company like {{Companyname}} sound interesting to you? Let me know if you have a little time to catch up soon. I am free most days around lunch, which I am hoping will make things easier for you.


Still did not respond. Another several days passes, then a new message comes in.

Date: Wednesday 10/09/2019 @ 06:15 PM

Subject: Re: Ready to Lead? // Product Security

Hey Randy,

I hope you are doing well. I wanted to follow up about {{Companyname}} and their Product Security Lead. These guys are {{trying to build startup credibility again}}. It would be an amazing experience and definitely a resume builder. Let me know if you'd be open to at least looking into it.

Thanks Randy!


In retrospect, the string “and their Product Security Lead” should’ve tipped me off to templating in use. But we’ll revisit that in a moment.

Originally, when a fourth email ultimately appeared, it surprised me.

Date: Friday 10/11/2019 @ 06:55 PM

Subject: Re: Ready to Lead? // Product Security

Hey Randy,

Just wanted to try you one more time. I am guessing either the role or {{Companyname}} itself didn't jump out at you. If you would like to be kept in mind for roles moving forward I'd be happy to share roles when they come up. You can also feel free to check out some of our current clients and see if any of them would be appealing. Below is a link.


If I don't hear from you, best of luck in your current role. If your situation changes at all, please keep me in mind.

Thanks Randy!


This one I did respond to, saying not interested. However, the overall level of persistence left an impression.

The majority of recruiters send me one message someplace, I ignore it, then we never interact again. A smaller share will follow up, but months later for a different job.

Hence, this guy Alex impressed me. I figured I could write some advanced software to orchestrate his email series but wasn’t aware of anything out there already.

Look at the fairly random timestamps! Look at the decently advanced templating of email content! 👏

And also, if this was some widely available SaaS, then why weren’t/aren’t more recruiters using it? Turns out I still cannot answer that question but seem to have identified one instance of such software.

An enterprising infosec recruiter could achieve what Alex did via Amplemarket. No affiliate relationship between them and me, just a respectful acknowledgement. I became aware of them via their Good Sales Emails site.

Interestingly, Amplemarket is geared towards plain ol’ selling stuff so infosec recruiting repurposes it somewhat. Makes sense to use it for this too, though.

You’d start by finding hackers already working decent jobs…

Amplemarket screenshot 1

Then you set up templates for positions you’re trying to fill…

Amplemarket screenshot 2

Before finally launching your attack…

Amplemarket screenshot 3

The Good Sales Emails site has examples of all this in action, like via this Gusto campaign or this one from ProsperWorks. A whole bunch.

Now that I’m aware of this, though, the effort from Alex is certainly less impressive and more plastic.

Again, we might think of all this alongside formulaic, “clickbait” titles. The first time I ever saw one, it was super effective. No doubt I clicked on whatever stupid thing was advertised.

But after learning more about online sales, persuasion, and certain formulas, I started actively avoiding things using these techniques unless it was an author or blog I otherwise trusted.

Screenshots of formulaic titles

I {{optional qualifier}} {{thing that you, unknown writer, personally did}}. {{Result statement preferably starting with "Here's"}}.

Not to say tech recruiters should “handwrite” every email. I get that you’re trying to scale efforts across a wide pool of candidates/fish and this is how you make a living. Still, anything that comes across as “mass-produced” is a big turn-off for star candidates.

Probably not desperate people who really need work but I can’t say for sure.

Going forward I will be wary of future techniques like these, and that fourth email is going to strike me as super annoying. 🌝