Freelance Video Streaming Engineer Jobs in Indiana

Gray Residential manages multifamily communities across the Midwest, and we've made a deliberate bet: we're not going to run on industry-standard software and settle for industry-standard results. We use RealPage as our operational backbone, but we're actively building custom tools - AI workflows, automation, internal applications, and data pipelines - that give our centralized leasing, collections, and property management teams an edge the rest of the industry doesn't have.

Building those tools is one half of the equation. Getting them adopted, used well, and continuously tuned in the wild is the other half - and that's where this role comes in.

We're looking for a Property Management Technologist to own the operational tech stack for our centralized teams. This is a new role, and it sits at the intersection of software, operations, and training.

What this role actually is:

• You are the bridge between the people building our internal tools and the people using them every day. Our Internal Software Developer ships the software; our Director of Centralized Leasing & Collections runs the team; you make sure the tools and the team actually work together.
• You'll be the primary owner of the tech stack across the centralized PM function - leasing AI assistants, collections workflows, reporting dashboards, RealPage extensions, and the AI-driven tooling we're rolling out across the portfolio. You won't manage people, but you'll lead the stack: deciding how tools get configured, when they get rolled out, who needs training, what's working, and what needs to be tuned.
• Day-to-day, the work breaks down into a few distinct streams:
• Implementation. When the dev team ships a new tool - an AI leasing assistant, a collections automation, a new dashboard - you own the rollout. Configuration, integration with RealPage and our other systems, environment setup, access provisioning, and the playbook that goes with it.
• Training and enablement. You'll lead onboarding and ongoing training for the centralized leasing team, the collections team, and site-level managers as tools roll down to them. That means live training sessions, written documentation, short video walkthroughs, office hours - whatever it takes to make the tools actually stick. Adoption is your metric, not just deployment.
• Tuning and iteration. AI tools in particular need constant care - prompts get refined, workflows get adjusted, edge cases get handled. You'll be the person doing that work: watching how the tools perform in production, gathering feedback from operators, tweaking configurations, and pushing structural changes back to the dev team when tweaks aren't enough.
• Stakeholder translation. You'll sit with a leasing consultant or AR specialist, understand what's slowing them down or where a tool is misfiring, and translate that into something the dev team can actually act on. You'll also translate the other direction - explaining what's possible (and what isn't) to operations leadership so we make smart bets about what to build next.
• You'll report into senior property management leadership and work day-to-day alongside the Internal Software Developer, the Director of Centralized Leasing & Collections, and regional and site PM leadership.

What we're looking for:

• This is a hybrid role on purpose, and the hybrid is real. We need someone who is genuinely fluent on both the technology side and the property management side - not an operator who's "comfortable with tech," and not a developer who'd like to learn the business. The people who do well here tend to share a few things:
• You're hands-on technical without being a software engineer. You can configure SaaS tools deeply, write SQL queries against operational data, build and tune AI prompts, wire up integrations with APIs and webhooks, and read enough code to understand what's happening when something breaks. You don't need to ship production features, but you should be able to debug a workflow without waiting on the dev team.
• You've worked in or close to multifamily operations. You know what a leasing funnel looks like, what delinquency management actually involves, and how a property manager spends their day. RealPage experience is strongly preferred - Yardi or comparable stacks are acceptable substitutes if you can show you've done the equivalent work.
• You're an exceptional trainer and communicator. The best tools in the world don't matter if the team won't use them. You can teach a 22-year-old leasing consultant and a 30-year property manager veteran the same workflow and get both of them productive - without condescension and without losing either one.
• You have real exposure to AI tooling. You've used LLM-based products beyond the consumer-grade chat interface - built prompts, tuned outputs, evaluated tool quality, and have a working sense of where AI helps and where it gets in the way. You're skeptical enough to spot when a tool is hallucinating and curious enough to keep pushing what's possible.
• You're metrics-driven. You'll be measured on adoption, accuracy, time saved, and operational outcomes - not on "tools shipped." You should be the kind of person who instinctively wants to see the data on whether something is actually working.
• You're based in or near Indianapolis and open to being on-site regularly. The work is close to the centralized team and the properties - proximity matters.
• Background-wise, this could come from a few directions: a property management operator who has grown into a tech/systems role; a RealPage or Yardi power user / implementation lead; a sales engineer or technical CSM from a proptech vendor; a BI/analyst with deep operational exposure. We care more about the pattern than the title.

What you can expect from us

• A real seat at the table while the centralized model and its tech stack are still being built. The decisions you make about how tools get configured and adopted will shape how this function operates for years.
• Tight collaboration with our Internal Software Developer and operational leadership - short loops between what gets built, what gets deployed, and what gets used.
• Direct access to ownership. The technology investment here is intentional and ongoing, and the people running the company want to know what's working and what isn't.
• Straight answers about comp, expectations, and how we measure success.
• If you're the kind of person who's been the "tech person" inside an operations team - the one who fixed the broken workflow, trained everyone on the new system, and quietly made the whole department run better - and you want a role that takes that skill seriously and gives you authority to do it at scale, we'd like to talk.