Executive Summary — WorkWingman¶
One page. The whole business.
What it is¶
WorkWingman is a free, local-first, privacy-first job-application Career Concierge. It runs on the user's own machine (Electron + Angular + .NET), stores everything in a local JSON store and an encrypted KeePass vault, and automates job applications across 15 applicant-tracking systems — auto-apply on 6 (Greenhouse, Workday, iCIMS, Lever, Paycor, Oracle) and assisted fill after sign-in on 9 more (UKG, ADP, Paycom, SuccessFactors, Microsoft Careers, Avature, Amazon, Google, Dayforce) — with a human always in the loop — it never auto-submits, never scrapes, never sells data. Users can bring their own AI key (BYOK) or use a managed option. WorkWingman is Black-owned and founder-built; that lived candidate perspective is where the consent-first posture comes from. Supplier-diversity eligibility is a partnership channel (see GTM), not the product story.
The problem¶
Applying for jobs is broken. Every employer uses a different ATS, forcing candidates to re-enter the same history endlessly. The AI tools that promise relief mostly sell "auto-apply to hundreds of jobs" — which spams employers, gets users' accounts banned, invites platform lawsuits, and monetizes by harvesting personal data. The market is loud, distrusted, and legally exposed.
The wedge¶
Trust is the moat. The job seeker — not the recruiter, not the employer — is our customer. A local-first, consent-first, quality-over-quantity Career Concierge is a genuinely different posture from every "spam cannon" competitor, and it's the only posture that later earns cooperation from LinkedIn, Workday, and employers instead of cease-and-desist letters.
How we make money (in this deliberate order)¶
| Stage | What we charge for | Why this order |
|---|---|---|
| 0. Free local core | Nothing | Build trust and a user base. This stays free forever. |
| 1. Paid individual convenience | Encrypted cloud sync, managed-AI option, resume variants, analytics (~$19/mo Plus, ~$29/mo Pro) | First real revenue; preserves ethos because the user still owns their data. |
| 2. Coach / school / workforce-org seats | Consent-gated shared dashboards for the people who help job seekers (~$10–12/seat/mo) | Durable, non-churning revenue. Fixes our worst problem (see below). Huntr already proves this wedge works. |
| 3. Consent-gated staffing | Candidate-owned workspace that staffing agencies can plug into with the candidate's permission | Real money, but gated so it never becomes recruiter surveillance. |
| 4. Verification / trust layer | A user-controlled "verified-claims wallet" | Big but late — it's FCRA legal territory. Ship consent-first, never as "truth scoring." |
| 5. Employer / ATS / verification partnerships | Integration fees for structured, consented, verified candidate data | Needs distribution leverage first. Partnerships are a late-game power move, not a seed strategy. |
The number that governs everything¶
Job seekers churn the moment they get hired. Codex-verified market reality: paid monthly churn in this category runs 12–25%, and Teal itself references users cancelling after landing a job. Pure prosumer economics therefore need ~80,000–120,000 active users just to cover a small team. The fix is Stage 2: institutional seats don't churn on one person's outcome, and repositioning from "job hunt" to "lifelong career management" keeps accounts alive after the hire. 50 orgs at 200 seats each ≈ $120k MRR — cleaner than chasing six-figure user counts.
The team (status-coded — see founding-team-recruitment.md)¶
- Andrew Jones — founder/engineer. Black-owned, founder-built; every commit review-gated by a multi-model AI pipeline.
- David M. Porter, Jr. — Offered: Cofounder & Executive Chairman (pre-papered conversion to President on full-time). Harvard OB PhD; ex-EVP Strategy, People + Culture, SF Fed; 12-yr foundation CEO ($20M+ raised); built UCLA's African-American Leadership Institute. Owns the Stage 2 institutional motion, governance, and the raise.
- Pamela Morris-Thornton — Offered, pending employer-conflict clearance: Cofounder & Chief People Officer (standing offer). Sitting CHRO of Advantage Solutions (~70k employees); 15 yrs Panera talent acquisition/exec recruiting/VP DEI. Owns the Stage 2 org-seat motion and Stage 5 employer credibility.
Rule: names appear on investor materials only with written permission; status is never fuzzed; a part-time seat is never presented as full-time headcount.
The market (comps and their outcomes)¶
- Simplify (YC W21, ~$1.2M raised, 1M+ users) — closest proof the free-core model works.
- Teal (Lerer Hippeau, Aleph, et al.; ~4M users; acquired Ramped in 2026) — proves the B2C paywall (Teal+ at $13/$29/$79).
- Huntr (Pro $40/mo + org/university/bootcamp plans) — proves the institutional wedge we're taking.
- LazyApply / Sonara / JobRight — the "apply to hundreds" cautionary set; volume sells but invites bans and spam reputation.
- Monster + CareerBuilder — filed Chapter 11 in June 2025; assets sold to BOLD for $28.4M. The old job-board model is dying; the trusted-candidate-tooling model is what's left.
What kills this (and our defense)¶
| Kill risk | Defense |
|---|---|
| Looks like a spam cannon → platform bans | Human-in-the-loop, human-pace, quality-first brand. Never market volume. |
| ToS/CFAA exposure from automating LinkedIn/Workday | Local assistive user-agent (like a password manager), user-authenticated, no server-side scraping. Partnerships, not scraping, long-term. |
| Structural churn wrecks unit economics | Institutional seats + lifelong-career repositioning. |
| No moat beyond an autofill extension | The moat is trust + the portable verified profile, not the autofill. |
| Connector maintenance overwhelms the team | Crowdsourced + centrally-pushed selector updates; budget 4–8 eng hrs/mo per ATS. |
| Verification liability (FCRA) | Ship as a consent-based claims wallet, not a consumer-reporting product. |
The ask / the near-term goal¶
Reach a trusted free-core user base and land the first 10–50 institutional seats (coaches, one bootcamp, one university career center). That combination proves both the ethos and the durable revenue engine — and is the credible on-ramp to the "Common App for jobs."
Full detail: monetization-strategy.md · financial-model.md · roadmap.md · legal-compliance-risk.md Plain-language mirror: ../business-plain/business-overview.md