Targeted Bets: An alternative approach to the job hunt

Targeted vs. Broad Applications

  • Many agree the core idea is “don’t spray and pray”: pick a small set of roles/companies you actually want and invest more effort per target.
  • Others note that early‑career or in very bad markets, pure volume has sometimes been the only thing that worked, because luck and timing dominate.

Contacting CEOs and Senior Staff

  • Strong disagreement here.
  • Critics: reaching out to CEOs or very senior people can look like bypassing the process, annoy HR/hiring managers, and get candidates quietly rejected or “soft blacklisted.” For large orgs, CEOs aren’t hiring anyway and are swamped with noise.
  • Supporters: at very small startups (5–20 people), the CEO often is the hiring manager; emailing them has directly led to hires. Some argue you “have nothing to lose,” and that a company which punishes polite outreach is a red flag.
  • Several distinguish between:
    • Emailing to get into the pipeline vs.
    • Emailing to influence a process you’re already in (seen as more problematic).

Cold Emailing Employees & Referrals

  • Some employees hate unsolicited outreach and ignore or resent it; they see “send multiple emails” as spammy.
  • Others say even if 90% ignore you, the 10% who respond can multiply your odds versus faceless ATS submissions, especially when a first‑round interview is the main hurdle.
  • Consensus points:
    • Don’t mass‑mail many people at one company.
    • Personalize, be genuine, and avoid AI‑generated “fake personal” emails.
    • Blindly asking strangers for referrals is often ineffective or viewed as deceitful.

HR, Recruiters, and Process Realities

  • One camp: HR/recruiting exists to shield managers and handle legal/logistical work; “going around them” creates friction and is often counterproductive.
  • Another camp: current funnels are so broken and automated that politely “causing trouble” may be the only way to get a human to look at your résumé.
  • Mixed views on HR quality: some see many HR/recruiters as checklist‑driven and low‑bar; others defend good recruiters as valuable filters and information sources.

Proof of Work, Networking, and Social Channels

  • “Proof of work” (projects, GitHub, personal sites, blogs, demos) is widely seen as powerful, especially when tightly aligned with the company’s domain.
  • Examples: custom personal sites, niche side projects, or domain‑specific hacks that make it “impossible not to talk” to the candidate.
  • But: real impact work is often under NDA; not everyone can or wants to code in their free time; some are reluctant to re‑enter social media for networking.
  • Suggestions include engaging substantively with people’s blogs or on technical social platforms as a slower but more human way to build connections.

Luck, Market Conditions, and Stage of Career

  • Multiple commenters stress how much plain luck and timing matter (e.g., preferred candidate drops out, team suddenly needs a fast hire, company is in a growth spurt).
  • Strategy interacts with market conditions: in today’s glut, even strong targeted outreach can be ignored; in fast‑growth phases, companies relax process and move quickly.
  • Having an existing job and financial cushion makes it psychologically easier to be selective and “play the long game”; without that, people understandably mix strategies, including broad applications.

Startups vs. “Make Your Own Job”

  • Some say “if you can’t find a job, build a startup”; others push back hard: startups are high‑risk, heavily luck‑driven, and usually harder than landing a job.
  • Several point out survivorship bias and the misleading narratives around guaranteed entrepreneurial success.

Systemic Ideas and Tools

  • A few wonder about job platforms that enforce targeted behavior (e.g., one application per day, “dream job” flags). Attempts at similar models reportedly struggled because neither employers nor candidates wanted to change habits.
  • There’s concern that advice like “email everyone” just shifts spam from HR to individual employees, continuing the arms race that led to heavy automation in the first place.