Who We Are:

Emerge Career’s mission is to break the cycle of poverty and incarceration. We’re not just building software; we’re creating pathways to real second chances. Through an all-in-one platform deeply embedded within the criminal justice system, we recruit, train, and place justice-impacted individuals into life-changing careers.

Our vision is to become the country’s unified workforce development system, replacing disconnected brick-and-mortar job centers with one integrated, tech-powered solution that meets low-income individuals exactly where they are. Today, the federal government spends billions annually on education and training programs, yet only about 70% of participants graduate, just 38.6% secure training-related employment, and average first-year earnings hover around $34,708.

By contrast, our seven-person team has already outperformed the job centers in two entire states (Vermont and South Dakota) in just the past year. With an 89% graduation rate and 92% of graduates securing training-related employment, our alumni aren’t just getting jobs—they’re launching new lives with average first-year earnings of $77,352. The results speak for themselves, and we’re just getting started.

Before Emerge, our founders Zo and Gabe co-founded Ameelio, an award-winning tech nonprofit that is dismantling the prison communication duopoly. Backed by tech luminaries like Reid Hoffman, Vinod Khosla, and Jack Dorsey, and by major criminal-justice philanthropies such as Arnold Ventures and the Mellon Foundation, Ameelio became a recognized leader in the space. Because of this experience both Zo and Gabe understood what it took to create change from within the system. After serving over 1M people impacted by incarceration, they witnessed firsthand the gap in second-chance opportunities and the chronic unemployment plaguing those impacted by the justice system. Emerge Career is committed to solving this issue.

Our students are at the heart of our work. Their journeys have captured national attention on CBS, NBC, and in The Boston Globe, and our programs now serve entire states and cities. And we’re not doing it alone: our vision has attracted support from Alexis Ohanian (776), Michael Seibel, Y Combinator, the Opportunity Fund, and public figures like Diana Taurasi, Deandre Ayton, and Marshawn Lynch. All of us believe that, with the right mix of technology and hands-on practice, we can redefine workforce development and deliver true second chances at scale.

Why We Do This:

Emerge Career was designed to tackle two systemic issues: recidivism, fueled by post-incarceration unemployment and poverty, and labor shortages in key industries. Over 60% of formerly incarcerated people remain unemployed a year after incarceration, seeking work but not finding it. The reality is shocking, workforce development programs are severely limited inside prison, with only one-third of incarcerated people ever participating. To worsen, the available prison jobs offer meager wages, often less than $1 per hour, and often do not equip individuals with the skills for long-term stable employment.

About the Role

We're looking for a scrappy, hungry operations generalist who is down to hustle, reflect on what's working, and figure out how to scale it. Someone who'll run through walls to support our growth initiatives — jumping into whatever's most broken or most promising in any given week, learning in public, and turning one-off wins into repeatable systems. If you read "operations generalist" and think "too vague," this role isn't for you. If you read it and think "finally, a job where I get to touch everything," keep reading.

The one question this role is obsessed with: how do we get more students to enrollment, successfully?

The way you'll answer it is by building experiences and spaces — online, in person, in community, inside facilities — that empower students to take the next step, and then reflecting hard on what actually worked. You'll notice the patterns, talk to the students who drifted, rewrite the playbook, and run it again next week a little sharper. The job isn't to stay busy; it's to figure out what actually moves students to enrollment and double down on it.

At this stage of the company, several things correlate with getting a student to enrollment. We think of them as one job because they share a single goal — a student enrolled — and they all draw on the same two core skills: creating spaces that set students up to succeed, and reflecting rigorously on what's working.

Scaling our LLM-powered student support. You'll answer tickets across text and email yourself — enough to deeply understand what students are struggling with — and then turn around and scale that work by training the LLM that handles the rest of our support volume. That means reviewing its outputs, improving its knowledge base, writing the reflections that make it smarter every week, and designing the Claude skills that let one person serve hundreds of students. Every ticket you answer is research; every pattern you spot becomes a system.
Grassroots, in-person community marketing. Emerge has a rare advantage: our work lets us embed directly in the communities our students come from. You'll run the on-the-ground recruitment that turns Emerge into a name brand in those neighborhoods — tabling at community events, building relationships with grassroots organizations and reentry networks, running info sessions, and hustling to iterate on what actually moves someone from "never heard of Emerge" to "enrolled at Emerge." We're excited about someone who'll treat this like a product: test, measure, kill what doesn't work, double down on what does.
Supporting and overseeing cohorts of students who are currently incarcerated. One of our goals this quarter is to figure out how to increase the success rate of students who start the program while still inside. We currently run cohorts at Rikers Island and in Massachusetts correctional facilities, and you'll help oversee and support them directly. That means you're comfortable going into jails and prisons, meeting students where they are, and doing the work to understand what it takes to set them up for success — both inside the facility and once they come home.

This job is perfect for someone who wants to be a founder one day. You'll do the three things every founder has to learn to do well: talk to users until you actually understand them, figure out what's working and what isn't, and then build the solutions that make the wins repeatable. You won't scale your impact by hiring more people — you'll scale it by writing the automations, Claude skills, and playbooks that let one person do the work of ten.

Who You Are

You love being student-facing. This role will often feel like case work, and you're drawn to that. You may have volunteered, worked in social impact, tutored, or spent time finding ways to make the playing field more fair. You find joy in helping others rise. You don't hesitate to call, text, or meet with a student who needs you. You show up consistently, personally, and with heart.
You believe everyone deserves a second chance. You treat everyone with dignity. You know how to meet people exactly where they are — with empathy and compassion — helping create a space where everyone feels seen and valued, regardless of their background.
You are entrepreneurial. You're scrappy, resourceful, autonomous, and low-maintenance. You know process matters — but at this stage, speed and iteration matter more. You're comfortable building quickly and changing procedures often to get to the right solution. You roll up your sleeves and solve problems. No job is too small.
You play to win. You stay optimistic when things get tough and keep moving when others slow down. You're not rattled by change or new ideas. You don't need to agree with everything, but you bring a "yes, and" mindset that helps ideas grow instead of shutting them down.
You work hard. You show up early, stay late, and do what needs to get done — no ego, no excuses. You don't wait around or ask for permission. This isn't a 9-to-5. The average person at Emerge is working ~60 hours a week. Nobody is micromanaging or breathing down your neck. If that sounds miserable, this isn't for you. If it sounds exciting, you'll fit right in.
You are a straight shooter. You don't shy away from hard conversations — internally or externally. You bring clarity, care, and accountability to every interaction.
You identify as a builder. You understand that recent advancements in AI have reshaped what it means to be a high performer, and you've taken that personally. You tinker with new tools the moment they drop. You've built Claude skills you're genuinely proud of — ones you still use, or ones you've handed to other people because they actually worked. You don't wait for permission to improve the way you work; you're already rethinking it. Nobody needs to tell you to keep upping your game — the only thing that slows you down is not having a sharp enough problem to point yourself at.
You are a tech optimist. You understand that not every part of an educational journey can or should be automated. Still, you believe that with the right builder mindset, smart tooling, and thoughtful design, one person can comfortably serve hundreds of individuals.
You're analytical, not just intuitive. You form opinions from evidence. You can look at a cohort and tell the difference between a signal and a coincidence. You're comfortable in a spreadsheet, you know how to read a funnel, and when the numbers point somewhere uncomfortable, you say so.

What We're Looking For (Minimally)

Willing to relocate and work in-person in New York City
You think analytically. Comfortable in a spreadsheet and able to look at a cohort, a funnel, or a pattern of behavior and draw a sharp conclusion. You should be able to point to a time you used evidence to change a decision.
You think in terms of repeatable systems. You believe most operations work can be abstracted into a playbook that an LLM or workflow automation can execute, and you're excited to build those playbooks rather than do the same task twice.
You want to be customer-facing. You're energized by direct contact with the people you serve. Phones, texts, in-person sessions, tough conversations — you want that, not just the quiet back-office work.
Demonstrated care for underserved populations — through work, volunteering, lived experience, or community involvement
You know the difference between being an AI user and an AI orchestrator. Anyone can type a question into ChatGPT. You're the person who wires models into workflows, gives them context, defines their roles, chains them together, and evaluates their outputs. You don't just consume AI — you direct it. If your current relationship with LLMs is "I ask, it answers," this role will feel like a big leap. If it's "I'm building the thing that asks and answers on my behalf," you'll feel at home.
Strong verbal and written communication skills. If you can't communicate clearly, you can't train an LLM, write a report, or communicate with a struggling student.

What You'll Do

Your north star metric is student enrollments. Everything below is in service of moving that number. A typical week will cut across all of it — one day you're running a cohort analysis, the next you're on the phone with a student, the next you're rewriting an LMS prompt or submitting an agency report. The through-line is always the same: what gets another student to enrollment?

Own LLM-powered customer service

Answer tickets across text and email yourself, with the quality bar of someone who actually cares about the person on the other end — and treat every ticket as a labeled training example, not just a closed conversation
Own the support knowledge base: curate ground-truth answers, keep retrieval-ready docs up to date, and prune stale content that's degrading response quality
Run evals on the LLM's outputs — build small test sets of real tickets, grade responses against a rubric (accuracy, tone, escalation logic, hallucination rate), and track quality over time
Iterate on system prompts, few-shot examples, and routing logic; A/B test prompt changes against the eval set before shipping them to production
Write weekly reflections on what the LLM got right, where it failed, and what changed in the prompt, knowledge base, or eval set as a result — so the team has a clear paper trail of how the system is getting smarter

Run grassroots, in-person community marketing

Show up where our students live — community events, reentry programs, workforce orgs, churches, barber shops, parole offices — and build real relationships, not transactional pitches
Run info sessions and small-group events that convert curiosity into applications
Partner with grassroots organizations and community leaders who already have trust in the neighborhoods we serve
Track what works: which channels, which messages, which partners actually drive enrollments — and iterate weekly
Help turn Emerge into a name brand in the communities that need us most
Execute in-person guerrilla marketing experiments across the five boroughs — targeting community based organizations (CBOs), homeless shelters, community events, and human services offices.
Test different neighborhoods, event formats, outreach tactics, and incentives to find what drives applications and converts to enrollments.
Track performance rigorously and report weekly on channel metrics, messaging insights, and recommendations for how to keep winning.
Synthesize learnings into replicable playbooks for the highest-performing strategies.
Activate and coordinate a network of 100+ brand ambassadors across the city.

Support students who are currently incarcerated

Oversee and support our cohorts at Rikers Island and in Massachusetts correctional facilities
Liaise with correctional facility staff
Write leadership reports
Work directly with students who are starting the program while incarcerated — understand their barriers, help them build momentum, and set them up for a smooth handoff to reentry
Bring every lesson back into the program — what worked, what didn't, what we should redesign

Benefits You'll Receive

Link

Emerge Career is making a dent in poverty. We are powering the skilled trades revolution, serving those who have been left behind by the system. If you want to put your fingerprints on something that actually changes lives, we'd love to hear from you.

Interview Process

About the Interview Process

Intro & Work Experience (20 min). We’ll chat briefly about the role and we’ll spend some time reviewing your interests and work experience.
Take-Home Challenge — We give you 3 days to prepare but only expect you to spend ~3 hours on it
Take-Home Review
Cultural Fit Interview (60 min)
Paid Work Trial (2–5 days) — You'll come onsite to work on a real project, with access to internal tools and team collaboration. You'll be paid $500/day. All travel expenses covered.
Reference Checks — We'll select 3–4 people you've worked with and request introductions when the time comes. We're looking for honest and raw, not flawless references.

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