Roadmap¶

Living document. Timeline is directional, not committed. Stages advance on triggers (real signals), not dates. Dates below are illustrative planning quarters from a notional Q3 2026 start.

The staged path at a glance¶

graph LR
    S0[Stage 0<br/>Free Local Core<br/>trust + distribution] --> S1[Stage 1<br/>Paid Convenience<br/>sync + managed AI]
    S1 --> S2[Stage 2<br/>Org Seats<br/>coaches, schools, workforce]
    S2 --> S3[Stage 3<br/>Consent-Gated Staffing]
    S2 --> S4[Stage 4<br/>Verified-Claims Wallet]
    S3 --> S5[Stage 5<br/>Employer / ATS Partnerships<br/>= The Common App for jobs]
    S4 --> S5
    S5 --> S6[Stage 6<br/>Optional Strategic Exit]

    style S0 fill:#e8f5e9,stroke:#2e7d32
    style S1 fill:#e3f2fd,stroke:#1565c0
    style S2 fill:#e3f2fd,stroke:#1565c0
    style S3 fill:#fff3e0,stroke:#ef6c00
    style S4 fill:#fff3e0,stroke:#ef6c00
    style S5 fill:#f3e5f5,stroke:#7b1fa2
    style S6 fill:#fafafa,stroke:#9e9e9e

Trigger table — advance when the signal fires, not on a date¶

Stage	Advance trigger	Primary goal	Success metric
0 → 1	Users ask for multi-device / backup / hate key setup	First revenue without breaking ethos	First 100 paying individuals; free core still growing
1 → 2	First coaches / a bootcamp ask to see client progress	Durable non-churning revenue	First 10 org seats live
2 → 3	Staffing agencies ask to source candidates	Add agency revenue safely	Consent-sharing flow shipped; 1 agency pilot
2 → 4	Employers + candidates want "verify once, reuse"	Portable trust	Verified-claims wallet v1; legal review passed
3/4 → 5	We have distribution + verified-profile volume	Partnerships from leverage	1 signed ATS/employer integration
5 → 6	Inbound strategic interest	Optional	N/A — outcome, not target

Illustrative timeline¶

gantt
    title WorkWingman — Illustrative Staging (triggers, not commitments)
    dateFormat  YYYY-MM-DD
    axisFormat  %b %Y

    section Stage 0 · Free Core
    Harden local core + ATS connectors      :done,    s0a, 2026-07-01, 90d
    Community seeding (privacy/dev + seekers):active,  s0b, 2026-08-01, 180d

    section Stage 1 · Convenience
    Zero-knowledge cloud sync               :         s1a, 2026-10-01, 120d
    Managed-AI gateway + billing (Stripe)   :         s1b, 2026-11-15, 120d
    Plus/Pro launch                         :milestone, s1m, 2027-02-01, 0d

    section Stage 2 · Org Seats
    Coach portal (consent-gated sharing)    :         s2a, 2027-02-01, 150d
    First bootcamp + university pilots      :         s2b, 2027-04-01, 180d
    Reposition to lifelong career mgmt      :         s2c, 2027-05-01, 120d

    section Stage 3-4 · Staffing + Verification
    Consent-gated staffing workspace        :         s3a, 2027-09-01, 150d
    Verified-claims wallet v1               :         s4a, 2027-10-01, 180d

    section Stage 5 · Partnerships
    ATS/employer integration + open profile schema :  s5a, 2028-03-01, 240d
    "Common App for jobs" schema public     :milestone, s5m, 2028-09-01, 0d

The "Common App for jobs" endgame¶

The north star (Stage 5) is an open, standardized, portable candidate-profile schema — verified, user-owned, consented — that works across employers and ATS platforms. Just as the Common App standardized college admissions, this eliminates the "ATS parsing tax" where every candidate re-enters the same history into every portal. WorkWingman owns the trusted client and the connector knowledge; the schema is the commons.

Crucially, the business reaches this without assuming any ATS cooperates on day one. Stages 0–4 build a real business on the user side. Partnerships (Stage 5) are the payoff of that leverage, not a prerequisite.

What has to stay true at every stage¶

Free core remains genuinely useful.
Human-in-the-loop; never auto-submit.
Local-first; cloud opt-in and zero-knowledge.
Job seeker is the customer; candidate data is never sold.

Plain-language mirror: ../business-plain/roadmap.md · Money behind each stage: financial-model.md