AI-Powered
Reentry
AI-enabled career pathways for people in custody, delivered through an adaptive learning platform.
This is not a course about artificial intelligence. It teaches people to use AI to do real work — and leave custody with proof that they can.
The Problem
People leave custody into a changed world — and a labor market where many traditional reentry jobs are closed to them.
New York law bars some people with convictions from security guard work. Similar restrictions affect home health aide, childcare, and many licensed healthcare roles.
Office and administrative work is the largest occupational group in the NYC metro area and is broadly open under Correction Law Article 23-A and the NYC Fair Chance Act, which covers nearly every NYC employer with four or more employees.
The barrier is often not eligibility. It is skills, evidence, and confidence with unfamiliar tools.
Lengths of stay and release dates vary widely, so a linear curriculum is a poor fit.
The Core Idea
There is a difference between teaching people about AI and teaching them to use AI to get hired. We do the second.
Productivity gain for novice workers using an AI assistant, versus 14% on average.
AI benefits less-experienced workers most, helping narrow the experience gap after custody.
An adaptive learning engine
Personalizes content, pacing, and support.
A working tool
Raises what a beginner can produce on real, employer-relevant tasks.
Briefly, a subject of study
Enough literacy to use AI safely and well — not a specialization.
Narrow by design, and additive
Not therapy, job placement, or a substitute for reentry services. We build skills, evidence, and credentials, then hand off to existing providers.
How the Program Works
Short modules, real tasks, and one target role — with the platform adapting as the participant works.
- 01Format
How the learning works
Short, adaptive modules: example, task, feedback, knowledge check. Plain-language, voice-supported, and multilingual.
Participants may opt into a short assessment at any point to move faster. It is never required.
- 02Foundations
Digital and financial literacy
Builds practical skills for daily life and reentry, skipping what is already mastered.
DevicesEmailPasswords & account securityOnline formsGovernment servicesIDNYC & SSNScam recognitionBank accounts & budgetingCreditPredatory-product awareness - 03Work readiness
Work-readiness essentials
Scenario-based practice in communication, conflict, feedback, and interviews.
- 04AI literacy
Using AI, not studying it
What AI can and cannot do; how to protect data, verify output, and refine a task.
- 05Pathways
AI-enabled career pathways
Each participant works toward one entry-level role. Pathways require NYC hiring demand, no statutory licensing bar, and AI that augments the role. Credentials stack along the way.
Office and administrativeRole AI leverage Credential stack T01Customer and client support Response drafting, knowledge-base search, escalation triage Northstar → IC3 L1 → employer-specific T02Administrative and operations assistant Drafting, summarizing, scheduling, document formatting Northstar (Word, Email) → IC3 L1–L2 → MOS Word T03Data operations and records QA Validation, cleanup, exception-flagging Northstar (Excel) → IC3 L2 → MOS Excel T04Bookkeeping support Categorization, reconciliation, exception review Northstar → IC3 L2 T05Research and documentation support Synthesis, SOP writing, structured summaries Northstar → IC3 L1–L2 Coordination and logisticsRole AI leverage Credential stack T06Scheduling and dispatch coordination Route and shift optimization, conflict resolution Northstar → IC3 L1 T07Warehouse, inventory, and logistics coordination Inventory reconciliation, documentation Northstar → forklift / OSHA-10 T08Facilities and building services coordination Work-order intake, vendor communication Northstar → IC3 L1 → BPI / OSHA Communication and communityRole AI leverage Credential stack T09Content production assistant Drafting, editing, image and copy production Grow with Google → Northstar (Social Media, Digital Footprint) T10Peer navigator / credible messenger Documentation, referral tracking, case notes Northstar → CHW certificate Advanced cohort — a stretch pathway, not a defaultRole AI leverage Credential stack T11IT help desk (Tier 1) Ticket triage, guided troubleshooting IC3 L1–L3 → Google IT Support → CompTIA A+ T11 has the highest ceiling and is realistic for a minority of participants.
- 06Evidence
Demonstrated skills and recognized credentials
Each pathway produces verified work samples, demonstrated skills, and relevant certificates.
What an employer can review- Processing a customer inquiry
- Drafting a professional response
- Entering information into a system
- Recognizing when to escalate
- Verifying AI-generated output
- 07Employer bridge
A bridge to employment
With consent, employers can review verified work; interview and early-employment feedback improves the pathways.
- 08Continuity
Transition planning support
Learning feeds the participant’s transition plan: documents, appointments, applications, and employment steps. It supports — not duplicates — Transition Coordinators and community-based providers, and follows the participant through transfer and release.
The Fortune Society and Petey Greene are existing DOC partners to co-design with, not compete against.
What Participants Leave With
Not a transcript — finished work built during the program.
A résumé
AI-assisted and targeted to a role.
A profile photo
Professional, plus a stylized version.
A personal website
One page, live at release.
A LinkedIn profile
Drafted inside, published at release.
A work portfolio
Role-specific samples employers can review.
Stackable credentials
Earned module by module.
A creative project
Music or an illustrated children’s book for their child, supporting family connection.
Everything is produced in a closed environment and published at release. Nothing depends on open facility internet access.
Evidence and Credentials
Two evidence tracks: recognized credentials and checkpoints showing progress from week one.
Northstar Digital Literacy
18 modules with certificates and open badges; used in correctional settings and promoted by the NYS Department of Labor.
IC3 Digital Literacy GS6 (Certiport / Pearson VUE)
Three stackable exams plus a master certification; Level 1 carries an ACE recommendation for one college credit; Credly badges.
Grow with Google — Career Readiness for Reentry
Free content co-designed with The Fortune Society, CEO, Defy Ventures, and The Last Mile.
Scenario-based checks of 8–15 items, at a fifth-to-sixth-grade reading level, voice-read and multilingual.
Mastery, not ranking: unlimited instructed retakes, rotating item banks, no comparative scores.
Earlier material returns at ~7, 30, and 90 days to measure retention, not completion alone.
Never used against a participant
Checkpoint results guide instruction and evaluation only — never discipline, classification, release, or risk decisions.
On existing infrastructure
Designed for DOC tablets, with no new hardware or open internet required.
Support for DOC Staff and Providers
The system flags needs for follow-up; it does not make decisions.
Less reconstruction, more contact
Authorized staff see progress, key gaps, engagement, and transition-plan milestones.
Aggregated reporting
Participation, completion, skill attainment, work readiness, employment outcomes, and agreed return-to-custody measures.
Not a surveillance tool
Individual data is never used for discipline, classification, release/legal decisions, risk assessment, or profiling. Educational records stay separate from criminal cases.
Security and Governance
Built for correctional environments and existing tablets, with two deployment models.
Closed, locally hosted
- Local deployment
- Curated knowledge base
- No open internet
- Comprehensive audit logging
Controlled-access connected
- Approved models only
- Filtered, logged gateway
- Data minimization
- Comprehensive audit logging
- Minimal data collection
- Role-based access
- Full audit trail
- No external data access without participant consent
Content is approved, version-controlled, and grounded. Sensitive guidance is partner-reviewed; uncertain outputs escalate to staff; quality, bias, and errors are monitored.
What the City Gets
A reentry program measured against agreed outcomes.
| Metric | Measurement window | Definition of success |
|---|---|---|
| Recidivism outcome | 3 / 6 / 12 / 24 months | Definition and comparison method agreed before pilot |
| Employment after release | Within 90 days | Placement confirmed |
| Job retention | 6 and 12 months | Retention tracked |
| Reentry stabilization | Continuous | ID, housing, benefits, appointments |
| Skill retention | 7 / 30 / 90 days | Repeat probes, not completion |
The specific recidivism outcome and comparison method will be defined jointly before the pilot begins.
Next Mile NYC showed at Rikers that pre-release training produces reportable outcomes: 99 CDLs earned, 64 hires, $90,200 average salary, no reported rearrests. This proposal extends the same logic to office and administrative work, which reaches far more people.
Beyond the numbers: existing staff and providers are extended, not replaced; continuity survives transfer and release; results rest on agreed measures.
How a Pilot Would Run
One facility, a limited voluntary cohort, and success metrics agreed before the pilot starts.
- One facility
- A limited, voluntary cohort
- A designated staff liaison
- A security and technical review of the two deployment models
- Success metrics agreed in advance
- The staff dashboard from day one
- Regular reporting
- Minimal operational disruption to existing programming
- Integration with existing education and reentry programming
- Interoperability with transition planning by contracted providers
Facilitated by our team or facility staff; longer term, a facilitator curriculum and certification so the program scales.
Stakeholder interviews; confirmation of the tablet vendor and its integration surface; whether proctored testing is permissible on-site.
One facility, voluntary cohort, staff dashboard live from day one.
Measured against the metrics agreed before the start.
Expansion decided together, on evidence.
Who We Are
The team combines years of direct program delivery at Rikers Island — with relationships across people in custody, facility staff, and DOC leadership — and experienced product and technology leadership.
The program is co-designed with community-based reentry providers and employers from the start.
Next Steps
- 01
A working session with the administration and DOC to align on goals, constraints, and security requirements.
- 02
Access for an initial needs assessment and co-design: stakeholder interviews and review of the tablet infrastructure.
- 03
Jointly define a limited pilot in one facility, with population, requirements, and success metrics agreed in advance.
Not a completed lesson or a certificate. A changed life trajectory: a person who leaves custody knowing what work they can do, able to get and keep it — and not returning.