[Hiring] AI Modernization Manager @Space Inch

Role Description

We're seeking an AI Modernization Manager to join us at Space Inch. You'll be embedded with one of our longtime clients - a fast-growing platform in the payments and commerce space serving thousands of merchants across physical and digital gift card programs. As the client has scaled, critical business logic has grown outside their core platform: undocumented legacy applications, scripts, and manual processes that keep the business running but that aren’t documented. This role owns discovery, planning, and coordination for the resulting modernization program, turning that hidden estate into a roadmap engineering can build against. AI is expected to be a big part of how you work day to day, not just for individual tasks but to build workflows the wider team can reuse for discovery, documentation, planning, and risk tracking.

Qualifications

• 7+ years of experience in product management, technical discovery, systems analysis, legacy modernization, or similar hybrid technical/delivery role - with product management experience a must-have within that mix
• Experience with application architecture, APIs, databases, integrations, reporting, scheduled jobs, and both cloud and on-prem infrastructure
• Proven ability to dig into an unfamiliar, poorly documented system - reading code, interviewing stakeholders, and reconstructing context that was never written down, without waiting for someone to hand you a process
• Ability to turn business and operational needs into requirements and plans that engineering can build against (i.e. architecture diagrams, runbooks, and monitoring/support handoff documentation)
• Understanding of the software delivery, release management, observability, support, and operational handover well enough to hold engineering accountable to it
• Excellent written and verbal communication skills, with experience operating at the intersection of engineering teams, business stakeholders, and external partners
• Readiness to push on missing information or challenging assumptions
• Hands-on experience using AI for investigation, analysis, documentation, or workflow improvement - not just familiarity with the idea
• Ability to read .NET code and architecture to evaluate designs, ask sharp questions, and sanity-check what engineering delivers, even though you won't be writing production code in this role

Requirements

• Experience with transaction systems or reporting platforms
• Experience with Windows-based legacy applications and hybrid (cloud + on-prem) infrastructure
• Experience working with or managing relationships with a managed service provider (MSP)

What You'll Do

• Technical and business discovery: Investigate legacy applications, scripts, and manual processes to understand what they do, why they exist, and what depends on them. Document how these systems actually behave and maintain a knowledge base.
• Modernization planning: Decide whether each capability should be kept, replaced, consolidated, automated, or retired, and turn that into a prioritized roadmap. Keep the roadmap current against real business priorities and deadlines.
• Delivery and stakeholder coordination: Coordinate initiatives from discovery through release and handover. Work across engineering, QA, Operations, business stakeholders, the MSP, and outside partners.
• Operational readiness and risk management: Ensure everything that ships has requirements, documentation, monitoring, and an owner behind it. Track material risks to resolution.
• Continuous improvement and AI-enabled workflows: Turn recurring manual work across discovery, planning, development, QA, release, and maintenance, into templates and reusable AI-assisted workflows for discovery, documentation, and risk tracking.

Qualities for Success

• Proactive investigator: You dig in and pull information out of both people and systems, and keep asking questions until undocumented context is actually reconstructed.
• Decisive planner: You can look at a messy capability and make (and defend) a real keep/replace/consolidate/retire call.
• Documentation-minded by default: Diagrams, runbooks, and written context aren't extra steps for you, they're part of how you think through a problem.
• Cross-functional communicator: Equally credible talking to an engineer about architecture and a business stakeholder about impact and timeline.
• AI-fluent, not AI-dependent: You build reusable AI workflows for discovery and documentation, but you verify what AI gives you against real sources.

Where You’ve Likely Developed These Skills

• Technical product management, systems analysis, or legacy modernization roles inside complex, legacy-heavy environments (e.g., fintech, payments, retail tech, or platforms going through modernization)
• Roles that required you to reverse-engineer systems with little or no documentation
• Consulting, agency, or professional services backgrounds where you had to build trust with a client's internal teams quickly

You're a Great Fit If You

• Genuinely enjoy the "detective work" of figuring out how something actually functions, not just reading the ticket about it
• Already use AI as part of how you investigate, document, and plan - and want to build that into repeatable team workflows
• Are comfortable challenging and verifying technical outcomes without being the one who designs or builds them

This Role is Not a Fit If You

• Prefer working from a fully specified backlog rather than building the picture yourself
• Are uncomfortable reading code or working directly with technical systems
• Have only surface familiarity with AI tools rather than real, hands-on use for investigation or documentation work

Compensation and Benefits

• Compensation: $4,500.00 – $5,500.00/monthly for a B2B engagement, based on experience and skills
• Remote-first setup
• Health & Wellbeing: 100% paid sick leave + annual health checkup
• Stay active: Wellness subsidy
• Continuous Growth: An education budget specifically designed to fuel your learning and help you expand your knowledge base.
• Extra perks: Referral bonus