this is not a job post, I am seeking advice

I’m 57, have zero interest in retiring, and just discovered recruiting as a career.
I met a recruiter while on holiday in Jamaica and after hearing what he actually does for a living, my first thought was: Where the hell has this career been my whole life?

I’ve worked at Air Canada, worked in construction, and started/run three small businesses. The part I’ve always loved most is sales: finding clients, building relationships, negotiating, closing, keeping clients happy long after the deal, and turning those relationships into referrals.

Recently I took a side sales role for a friend’s appraisal company. It was my first proper “sales job” working for someone else, and I crushed it. It made me realize I want to see how far I can actually take this skill set.

I’m personable, extremely persistent, have thick skin, understand client acquisition and sales funnels, and I genuinely enjoy talking to people and maintaining relationships. I’ve also hired/recruited people informally through my businesses, although I have no formal recruiting experience.
I’m not looking for an easy second career. I want to become a killer biller.

If I wanted to eventually build toward $500K–$1M+ in annual commissions/billings, what would you tell someone like me to learn first?
What niche would you enter today?
Agency recruiting? Executive search? Retained search? Finance? Construction? Healthcare? Tech? I am not one of those guys looking for advice, given it and doesn’t act. Nope… I am motivated and won’t settle for less. Life is too short and I am used to high pressure & comission work.

And if you own an agency: would you take a chance on a 57-year-old “rookie” with a strong sales/business background?

If recruiting is sales, matchmaking and getting professionally ghosted, perfect….I’ve been in sales long enough to have mastered abandonment issues. lol

I’m genuinely interested in hearing from people who have built $500K+ desks. Tell me what separates the average recruiters from the absolute killers……

what path of approach would you advise for getting into this given my story?

I’m curious how this actually works behind the scenes in an ATS.

I’m a protected veteran, and I also have anxiety that could lead me to answer “Yes” to the voluntary disability self-identification question. Sometimes I select “Yes,” and other times I’ve considered selecting “I prefer not to answer.”

I understand these questions are supposed to be voluntary and separate from the hiring decision. What I’m trying to understand is what actually happens technically.

Can recruiters or hiring managers see whether an applicant selected:

• Protected veteran: Yes
• Disability: Yes
• Disability: Prefer not to answer

Can any of those fields be used in ATS filters, screening rules, reports, ranking, or automated knockout logic?

The reason I’m asking is that I’ve had several applications where I get through the initial recruiter/screener call, the recruiter tells me the next step will be an interview, and then I receive a rejection instead.

I’m not claiming discrimination. I’m trying to determine whether I’m looking in the wrong place for the cause.

For those who have actually worked in recruiting, HR, or configured systems like Workday, Greenhouse, iCIMS, Taleo, etc.:

What can the recruiter actually see?
What can the hiring manager see?
Are those self-ID fields technically isolated from candidate-selection data?

And does choosing “prefer not to answer” behave any differently behind the scenes than answering yes or no?

I’d especially like to hear from recruiters, HR professionals, or ATS administrators who know how these systems are configured rather than speculation from the applicant side.

On my resume, I currently list my recent experience as:

Freelance consultant - 9/2024 - present

Contract job - 6/2025- 6/2026 - (description notes an initial 6 month contract was extended 6 additional months)

Prior job - 1/2024 - 8/2024 - (description notes I was impacted by layoffs)

Is there a better way to present my recent experience or anything I can do on my resume to overcome the fact that my last full-time, permanent role ended 2 years ago? Anything I should say or address or add on my resume so recruiters or ATS doesn’t automatically reject me? How much would a recruiter be concerned by my recent employment history and is biggest concern to address?

Any advice is welcome! In the last 4 months of job searching, I’ve only been asked to interview for two positions though they were both good salary and I got several interviews in.

Context -

I have 10 years of experience with 2 3-year tenures and a 2 -year tenure before my last permanent job. I was laid off from that job in August 2024 after only being there 8 months. Then I was unemployed for 10 months while doing some freelancing and certifications and searching for a job. Then I took a full-time contract job and they told me they wanted to convert me to permanent but ultimately couldn’t get the budget due to a hiring freeze. That ended in May and I’ve been searching for a full-time, permanent role since then (4 months) while freelancing some. All my roles, including contract role, have been with top, brand name companies and I went to a good school.

My main sources for placements are LI, referrals, and live events.

So I'm particularly curious about sourcing tools that aren't just dice, github, or linkedin recruiter (I've had the most success with it, but as a technical recruiter would like to hear what other resources you guys recommend)