My e-mail conversation with a recruiter about 1099 work

I recently updated my resume and posted it on and because I wanted to see what 1099 gigs I might be able to take on in 2022. While I will probably continue with at least one of my current projects, it's always good to feel out the market.

This is based on Chapter 8 of my book: How to "Apply" for 1099 Jobs.

With the 1099 job application method, it is basically a numbers game. I'd say only about 10% of recruiter conversations turn into viable 1099 leads.

Below is a copy of my e-mail conversation with a recruiter. This one didn't pan out but I just want to show you a real life example of how simple this Going 1099 method is at the outset.

I've pulled out the recruiter's name and the company's name but otherwise the text is an exact copy of our e-mail conversation.

1) Initial e-mail from the recruiter


Good afternoon! My name is [recruiter name], I am the Talent Acquisition Sector Lead for the SES/Systems Engineering Sector here at [company name].  I’m currently supporting a number of prime contracts that are aligned to the Space/Systems Engineering Business Group. 

I wanted to contact you and introduce myself, I recently came across your profile on and was impressed with your resume.  Your background and experience align well to the current work we support and I was curious to see if you might be interested in hearing more about current opportunities we have available. 
One of the teams I support is very interested in your qualifications, they requested I reach out to you personally.  I have a Senior Manager who leads the Digital Engineering Team who is interested in speaking with you about several opportunities supporting his Data Analytics Team. 


Before scheduling that call, I was hoping to identify a convenient time for you and I to connect.  I’d like to get a better understanding of your current situation and gather some additional information.  The call would serve as more of an informal information gathering session and take no more than 25 minutes or so.  I would also use the time to provide you with additional insight into the program and answer any remaining questions you might have.  If you were interested in moving forward after our call, I could schedule a date and time for you to speak with the interested managers respectively. 


I will provide my availability for the remainder of the week below, I’ll be out of the office Thursday and Friday for the Thanksgiving holiday.  I’ll also include availability for early next week as well in case tomorrow isn’t convenient.  At your convenience, please let me know if there may be a date/time that works best.  I’ll do my best to accommodate your schedule. 


Thank you for your time and consideration, I look forward to your response!



Wednesday, November 24th, 2021 – 8:30 AM to 1:30 PM – 3:00 PM to 5:00 PM

Monday, November 29th, 2021 – 9:00 AM to 11:00 AM – 12:00 PM to 2:00 PM – 4:00 PM to 5:00 PM

Tuesday, November 30th, 2021 – 8:00 AM to 10:00 AM - 3:00 PM to 5:30 PM

[Recruiter Name] Sector Lead - Talent Acquisition

Systems Engineering/Intel/Space Programs

2) My initial response

Hi [Recruiter],

Thanks for reaching out. I actually work with some of your colleagues on the [my contract] at NGA. Great staff! If the Digital Engineering Team is working on the [program] effort then I may have even met a few folks.

Happy to chat more but before we schedule anything, I wanted to let you know that I’m primarily looking for 1099/sub-contracting projects with a firm-fixed price structure. 

I understand you’re probably looking for W2 personnel but if the above isn’t a deal breaker I’m happy to continue the conversation.

 Have a great Thanksgiving!


3) My follow up after Thanksgiving

Hi [Recruiter],

Hope you had a nice Thanksgiving. 

Wanted to make sure this didn’t get lost in your inbox. 

Doing some 2022 project planning so if your PMs are up for the 1099/sub contracting route would definitely be up for a chat to see if it makes sense. 

If not just let me know and we can stay in touch for future opportunities to work together. 



4) Recruiter's response where he says 1099 is a no-go


Good afternoon,

I hope you had an enjoyable Thanksgiving holiday as well! 

I spoke with the PM during our 8:00 AM meeting this morning, he confirmed that the program isn’t willing to move forward with any 1099 arrangements. 

I can’t say I was the least bit surprised as that is typically the policy of most larger integrators but I figured it was worth a shot.  I certainly appreciate your response to my initial email and for following up with me today.  It is a small community and I would welcome the opportunity to stay in touch, you never now when we may cross paths again! 

Thanks again Dale!



5) The last e-mail from me

Appreciate you checking [Recruiter]!

I’ve found the 1099 sub-contracting opportunities with larger primes to be dependent on a few things (namely how hard it is to fill a spot) so I figure it’s always worth checking. 

Let’s definitely stay in touch and thanks again!



Note how all this was perfectly pleasant and reasonable. Now, I think that if the program has a hard enough time recruiting W2 employees for this particular team the PMs will start being more flexible about 1099/sub-contracting. But, I'm not going to force the issue.

For every 10 of these conversations I have, perhaps one or two will lead to concrete 1099 conversation. 


If you're interested in learning how to use the job application method to go 1099, you should pick up a copy of my book.


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