At Green Irony, we exist to turn AI into Actual Intelligence — accelerating outcomes and proving that complexity is optional.
We don't just build AI-native systems for our clients; we run our own company on them. Quoting, hiring, delivery, account management — the same stack we implement for customers is the stack we operate on every day. It lets a small team deliver like one 10x its size: enterprise-grade integrations shipped in weeks, not months, by senior US-based engineers working alongside AI.
We hire people who automate first, bias hard toward action, and treat ownership as a default setting. If you'd rather govern yourself than be governed by layers of project managers, welcome home.
We need someone who can own the client experience and the delivery across a portfolio of engagements, the person who makes sure every client feels well-served, every project stays healthy, and nothing falls through the cracks.
If you’ve managed technical project delivery, built strong client relationships, and get energy from keeping a lot of plates spinning without dropping any, keep reading.
What You’ll Actually Do
Own the client relationship. You’re the primary point of contact from kickoff to closeout. Clients trust you, lean on you, and come back because of you. You communicate proactively, and they never have to chase you for a status update.
Own the plan. You’ll run up to 20 concurrent engagements ($30–50K, 3–8 weeks), coordinating small engineering teams alongside our AI-powered delivery tools. You track milestones, flag risks early, unblock teams fast, and keep work moving before anyone has to ask. AI handles documentation and reporting overhead so the volume stays manageable.
Run the engagement from kickoff to hypercare. You run a structured cadence: 30-minute kickoff, 2–3 discovery sessions, FRD review, UAT, and hypercare. You author the FRD with AI, lock first discovery within seven business days, and clear open items before development starts. Status goes out every Monday. Every meeting has a purpose, an agenda, and a result.
Hold the line on scope and commitments. You enforce scope discipline so projects stay profitable and clients get exactly what was promised. Out-of-scope requests go through a change request before work begins. No exceptions, but you handle it in a way that strengthens the relationship rather than straining it.
Operate from inside Claude. Claude is your primary interface, not a tool you reach for occasionally. You use it to pull context (SOW summaries, account history, project health briefings), to run the skills that produce client-facing artifacts (kickoff deck, discovery questionnaire, FRD, UAT guide, weekly status report), and to keep Notion — our system of record — current. The scrum agent reports project status into a dashboard you act on; you don’t chase engineers for updates.
Spot the next dollar. You’re the eyes on the ground inside the account. Spot follow-on projects, managed services opportunities, and adjacent problems we could solve. Loop in sales when there’s something to chase — you don’t close the deal, but you make sure it never gets missed.
What We’re Looking For:
- 4+ years experience in technical project management or client delivery at a software services or consulting firm, owning plans, milestones, and engineering coordination across multiple concurrent engagements.
- Working knowledge of Salesforce and/or MuleSoft — enough to speak the language credibly and spot when something's harder than estimated, but deep architecture or implementation experience isn't required (AI handles that layer).
- Comfortable in a Kanban-style, agent-orchestrated model where daily status comes from a scrum agent and project health is a dashboard — if you need sprint cadence and ticket grooming to feel productive, you'll be miserable here.
- Exceptional written and verbal communication — clear, concise, confident, and warm.
- A high-volume, high-context-switching operator who can hold 15–20 active engagements and switch between them cleanly — volume is the role, not a phase you're trying to grow out of.
- Schmoozer with an engine — you build warm relationships clients refer to peers, but when something needs to move, you move it.
- Hungry, ambitious, highly coachable — you'd rather be corrected fast than be comfortable.
- A bias for action, decisive under chaos. You act first and analyze second; if you need exhaustive context before committing, this role will eat you alive.
- Hands-on experience using AI tools (Claude, Cursor, ChatGPT, or similar) as part of your day-to-day workflow
Even better if you have:
- Experience selling, supporting, or delivering to small and mid-sized businesses (law firms, professional services firms, finance teams) where the buyer is rarely the technical user
- Background in SOW-driven engagements where you’ve managed scope, change requests, and project-based billing
- Experience as an Engagement Manager or Delivery Manager at a consulting or SI firm
How You’ll Be Measured
- CSAT — you own the score, not just contribute to it
- Partnering with the Engineering team to deliver the project on-time, and on-budget.
- Scope control and change request compliance
- Invoice accuracy and collections timeliness
- Responsiveness and turnaround time
- Project portfolio health and quality of executive reporting
- Discovery-to-build velocity (first discovery within seven business days of kickoff; FRD ready before development starts)
- Account expansion radar (follow-on opportunities and managed services contracts identified and routed to sales)
- Hypercare quality (defect volume during hypercare, tracked separately from build defects)
At Green Irony, you…
- Take full ownership of your work—proactively solve problems and drive deliverables to completion.
- Relentlessly pursue outcomes, measuring success by delivered value, not just output.
- Solve complex problems with practical, innovative solutions.
- Communicate directly, transparently, and with positive intent—focusing on clarity, not politics.
- Grow continuously—mentoring, learning, and automating to expand your impact.
- Competitive salary + performance bonus
- Medical, dental, and vision coverage
- 401(k) with generous company match
- Flexible PTO and remote-first work environment
- Annual professional development budget (certifications, conferences, AI tools)
- Equipment stipend
Green Irony is an equal opportunity employer committed to building an inclusive team where diverse voices drive better outcomes.
We evaluate all qualified applicants without regard to race, color, religion, gender, gender identity, sexual orientation, national origin, veteran status, disability, or any other protected classification—because the only bias we tolerate is toward delivering excellent work.
Similar Jobs
What you need to know about the Chicago Tech Scene
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
