Beyond Your Network: How LLMs Can Expand Your Job Search Horizons

Tackling The Job Markets with Assistance from Web-enabled LLMs

It's been a while since I've been in the open job market looking for a new opportunity. I've spent the last 7 years in co-founder, founder, and a C-suite role (my friend was CEO) in early stage startups (pre-seed to Series B), so it's been quite some time since I've filled out a resume or done a fresh look at the (limited) job market. I wanted to widen my aperture a bit, but keep opportunities consistent with my background, which are pretty closely correlated with my interests.

Given that, I figured I'd ask a verbose and knowledgeable friend, ChatGPT, for some help thinking of new sectors, companies, and roles to consider outside of my initial hit list. I want to throw myself into a mission and role that I can really dig into and contribute at large scale, and I didn't want to limit myself with my personal network biases. So, PDF of my resume and a prompt and we were off to the races.

My Prompt

You know me. See attached resume. We've talked a lot.

The job markets are tough for junior and senior applicants alike. I'm wondering if you have any ideas for blind spots I might be missing in terms of companies or sectors I should consider outside of Mag 7/FAANG+ hyperscalers, well-funded AI labs, and Series B and beyond startups. Given my background, do you think tehre [sic] are other areas I should be considering?

The Response: Ranges of Verbosity & Angles of Attack

ChatGPT (this was GPT-5) performed as it always does with me based on my profile/system prompt, and then iterated in the fashion I always encourage it to do. All of that combined returned the following for me. I thought it did a pretty good job, giving me macro to micro ideas, and then generating brief helpful outreach message blurbs for DM'ing on LinkedIn or shooting a quick email – these were solid, IMHO, and mostly accurate with respect to my bio (with a bit of the usual LLM hallucinatory embellishment—it gave me credit for "leading" things where I was part of a team).

I'm definitely using this though, I'll give it that. If action following this is a measure of success, then this response passed muster. :)

The Output

Succinct Areas to Explore

Strategic enterprise labs / R&D groups — Fortune 500s with "skunkworks" innovation teams (Walmart Global Tech, Disney Imagineering, Comcast NBCU R&D, Ford Model e, etc.) value 0→1 product execs.

Infrastructure & middleware providers — Companies in developer tools, vector DBs, orchestration, observability, and "picks & shovels" of AI (e.g., Pinecone peers, LangChain, Weaviate, Modal, Hugging Face).

Media & entertainment convergence — Streaming platforms, sports/venue tech, music rights management, podcast/creator economy infra — all adjacent to your Amazon MP3, Atom Tickets, and DeepCast history.

B2B SaaS in "boring but big" industries — Proptech, fintech infra, legaltech, govtech, logistics, compliance — sectors where PMs who can translate user need → tech stack are scarce.

Private equity portfolio companies — PE-backed rollups or carve-outs (Vista, Thoma Bravo, TPG, etc.) often seek interim CPTO/CPOs to scale or modernize product infra.

Corporate venture arms / venture studios — EIR-style roles (GV, a16z Speedrun, AlleyCorp, Madrona Labs, Samsung Next) fit your prior Artium/Brass Pen attempts.

Civic & public good tech — Nonprofits or B-corps in workforce development, sustainability, or policy tech (you've got civic engagement credibility ).

International firms expanding to U.S. — Fast-growing EU or APAC tech companies needing U.S. product/GTM leadership to land and expand.

Career Exploration Matrix: Sectors, Companies, and Positioning Blurbs

1. Sectors & Example Companies

Strategic Enterprise Labs / R&D Groups

Infrastructure & Middleware Providers (AI Picks & Shovels)

Media & Entertainment Convergence

B2B SaaS in 'Boring but Big' Industries

Private Equity Portfolio Companies

Corporate Venture Arms / Venture Studios

Civic & Public Good Tech

International Firms Expanding to U.S.

2. Résumé Mapping: Credibility Stories

Strategic Enterprise Labs / R&D Groups

Amazon MP3 $0→$300M; scaled consumer infra; 0→1 spaces for skunkworks.

Infrastructure & Middleware Providers

DeepCast, Prompt Yield; end-to-end AI infra; translating infra into adoption.

Media & Entertainment Convergence

Amazon MP3, doubleTwist, Atom, Rival, DeepCast; at every disruption point in media.

B2B SaaS

Azibo, Fernish; simplified workflows, scaled ops-heavy SaaS.

Private Equity Portfolio Companies

Thinknear → Telenav → inMarket; MedianNet; familiar with PE cadence.

Corporate Venture Arms / Venture Studios

Artium EIR, Brass Pen, DeepCast; validated/killed experiments fast.

Civic & Public Good Tech

Volunteer history with PledgeLA, UNITE-LA, Riordan C2C; blends mission + market.

International Firms Expanding to U.S.

Amazon MP3 global launches; Fernish multi-city expansions.

3. Positioning Blurbs (Outreach Ready)

Strategic Enterprise Labs / R&D Groups

I've repeatedly turned early-stage ideas into scaled revenue streams — from Amazon MP3's $0→$300M ramp to launching new consumer surfaces at doubleTwist and Rival. I thrive in ambiguous, 0→1 spaces, particularly at the intersection of design, GTM, and engineering. I'd love to explore how your lab is approaching next-gen digital products.

Infrastructure & Middleware Providers

My recent work at DeepCast and Prompt Yield involved building full AI stacks — SST/ASR, LLM orchestration, vector DBs, and real-time GTM layers. I specialize in translating developer infrastructure into products real users adopt. Curious if your team is looking for someone to bridge bleeding-edge AI infra with adoption and growth.

Media & Entertainment Convergence

I've built products at every disruption point in media: DRM/streaming (Amazon MP3, doubleTwist), ticketing (Rival, Atom), and podcast intelligence (DeepCast). My sweet spot is marrying fan engagement with scalable platforms. Would love to discuss how your team is thinking about the next wave of creator/entertainment tech.

B2B SaaS

At Azibo and Fernish, I simplified complex workflows for landlords and renters while scaling SaaS ops nationwide. My strength is making compliance-heavy, operationally complex industries usable and delightful. If you're looking to modernize enterprise SaaS in legal, proptech, or logistics, I'd be eager to bring that lens.

Private Equity Portfolio Companies

I've lived the PE cadence: Thinknear's scale and exit, MedianNet's product modernization, and corp dev deal work. I know how to modernize product orgs, hit EBITDA targets, and prepare companies for sale or roll-up. If you're looking for a CPTO/CPO who can drive both transformation and outcomes, I'd be a strong fit.

Corporate Venture Arms / Venture Studios

I've founded, incubated, and sunset ventures — from DeepCast to Fernish to Brass Pen — and I know how to validate fast, scale what works, and kill what doesn't. My bias is toward action and storytelling that secures buy-in. Would be excited to plug into your studio's pipeline as an EIR or product lead.

Civic & Public Good Tech

I've paired commercial product rigor with civic engagement — volunteering with PledgeLA, UNITE-LA, and Riordan C2C while building companies like Fernish and DeepCast. I believe civic and workforce tech needs product leaders who understand both mission and market. I'd love to explore how I could help scale impact in your org.

International Firms Expanding to U.S.

I've led global launches (Amazon MP3 into EU/JP) and multi-city U.S. expansion (Fernish across LA, Seattle, Austin, Dallas). I know how to adapt product, ops, and GTM across new markets. If you're building your U.S. footprint, I can help bridge international strategy with on-the-ground execution.