Remote Property Management Bookkeeper Jobs in Madison, WI

We're Changing the Rentals Industry

We're a profitable, growth-stage company building industry-leading martech and data products for the PropTech space. Our focus is on our category-leading AI and data SaaS products with triple-digit growth rates.

We're a fully remote team of 100+ spread across the U.S. from coast to coast. We operate on a strict no a**holes policy and are proud to have built a community of highly performant people that take our work seriously, but not ourselves. And, we're looking for exceptional people to help further accelerate our growth.

While we've raised $30MM+ to date from some of the world's best investors, we're profitable with a strong balance sheet and an indefinite runway. We pride ourselves on achieving rapid growth without having to incinerate capital.

About Our Products

ApartmentIQ is the all-in-one data platform powering smarter decisions across multifamily - covering 40M units with daily property and market intelligence used for surveys, research, and revenue management. We're trusted by 65% of the NMHC Top 50. MavenAI, delivers AI-powered marketing automation built by industry experts and integrated directly with property management systems, serving over 2M units.

Our customers use ApartmentIQ to decide what to charge for real apartments. That number comes out of a pipeline you would own: data pulled from the property management systems that run the industry, fed through demand and renewal models, and surfaced as pricing recommendations that get acted on the same day.

We're hiring a staff-level engineer to own that path end to end. It's a wide role by design - Python for the ML and ingestion services, Terraform for everything they run on, Ruby for the application layer that customers touch. Often all three in one change. If you like owning a system rather than a layer, this is that job.

• Own a system that sets rents. Demand models, renewal probability, price elasticity, compliance scoring - you'll own the pipeline that produces them and be accountable for the recommendations landing correctly.
• Solve a genuinely hard data problem. Property management systems are walled gardens with inconsistent APIs and no shared identity model. Getting clean, reconciled lease and charge data out of them is the core technical challenge of this role, and we're rebuilding it from scratch right now.
• Build the infrastructure you depend on. Every database, queue, and role is in Terraform, and you'll write it. No ticket to another team to get a table provisioned.
• Build the orchestration layer. Ingestion, inference, and the downstream daily jobs need to run in the right order, gate on their inputs being ready, and recover cleanly when something upstream is late. You'll own that coordination layer end-to-end — today it's cron and careful timing; you'll make it a real pipeline.
• Prove the numbers are right. Build out the observability and alerting across the data architecture — pipeline health, data freshness, and recommendation drift — so a bad number gets caught before a customer prices a lease against it.
• Work across the whole stack, for real. Python, Terraform, and Ruby are all first-class parts of this job, not a "some exposure to" bullet.
• Set the bar on AI-assisted engineering. A large and growing share of what we merge is AI-assisted. We want someone with strong opinions about how to do that well and the review judgment to enforce them.

• You want scope, not scaffolding. You're looking for a system to own outright, and you'd rather have a hard problem and autonomy than a well-defined ticket queue.
• You care that it's correct. These outputs move real money. You build the checks that prove it, and you notice when a number looks wrong.
• You go end to end. Empty repo to production, including the alarms, the backfill, the runbook, and the migration nobody scoped.
• You raise the level around you. Your reviews make other people's code better, and work quietly moves off other plates once you're there.
• You have strong opinions on AI-assisted engineering. You lean on it to ship to customers faster but you have the discipline to uphold code quality standards.

• Proven Track Record: 8+ years building and operating production systems, with real ownership of something significant.
• Python Depth: Strong Python in a serverless or service context - AWS Lambda, container images, dependency and runtime management, multi-stage job orchestration.
• Infrastructure as Code: Hands-on Terraform. You've stood up a production data store yourself, including the IAM, encryption, networking, and alarms around it.
• Data & SQL depth: Fluent in analytical SQL and data modeling - you've built and debugged multi-stage warehouse pipelines (ours run on Redshift) and reconciled messy source data into something trustworthy. You've worked across the major database paradigms - relational, key-value/document, and search — and know what one is the best tool for the job at hand.
• Ruby on Rails: You can own changes across a large Rails codebase, even if it's not where you've spent the most time.
• Cloud Native: Deep AWS across Lambda, S3, SQS, Kinesis, EventBridge, DynamoDB, Aurora/RDS, Redshift, and IAM.
• ML in Production: You've kept models serving correctly over time - versioning, dependency drift, feature plumbing, explainability. You don't need to have trained them.
• Adaptable & Autonomous: Experience navigating a fast-paced, growth-stage environment where priorities shift and ownership is expected.

Nice to Have

• Golang experience
• Web scraping at scale (Playwright or similar)
• OpenSearch index management and tuning
• SOC 2 or similar compliance and security remediation work
• xgboost, scikit-learn, or SHAP
• Multifamily, PropTech, or revenue management domain experience

Why Choose Us:

• Remote-First: We offer the freedom to work from home across most of the U.S. You'll enjoy the flexibility of remote work, balanced with high-energy in-person offsites to build real connections and celebrate our wins together.
• Competitive Compensation: We believe in hiring the best and paying accordingly. You'll receive a competitive salary that reflects your impact and expertise.
• Paid Time Off: Take the time you need with our flexible vacation policy and dedicated paid parental leave to support you and your family's biggest milestones.
• Your Health Matters: Stay healthy with high-quality Medical, Dental, and Vision insurance plans for you and your family.
• Peace of Mind (On Us): We fully invest in your security with 100% company-paid Short-Term Disability, Long-Term Disability, and Basic Life Insurance.
• Protection for Your Whole Crew: Access supplemental insurance for the unexpected, plus specialized coverage to keep your pets happy and healthy, too.
• Invest in Your Future: Secure your financial goals with our 401k Program, helping you build for the long term while you help us build the company.

If you need assistance and/or a reasonable accommodation in the application or recruiting process, please contact your recruiter.

Applicants must be authorized to work for any employer in the U.S. We are unable to sponsor or take over sponsorship of an employment Visa at this time.

We want to alert you to potential recruiting scams targeting job seekers. Please note that our company will never request payment, personal information, or any confidential details during the interview process.