Build the future of
real estate finance

RealBooks is looking for a Product Owner who lives at the intersection of real estate investing and product strategy. You'll own the product backlog, define priorities, and serve as the primary liaison between our business stakeholders and our development team based in Moldova.

This is not a passive backlog-grooming role. You'll work directly with the CEO, COO, CIO, and advisory board members to translate business vision and customer needs into actionable delivery plans. You'll also engage directly with customers and industry leaders to gather feedback, identify market gaps, and shape the product roadmap.

What you'll do:

• Own and prioritize the product backlog based on business strategy, customer feedback, and market opportunity
• Serve as the day-to-day liaison between RealBooks leadership and the engineering team in Moldova, managing communication across time zones
• Translate complex real estate finance and tax concepts into clear product requirements and user stories
• Field feature requests from customers, advisors, and industry partners — evaluate, prioritize, and communicate decisions
• Participate in sprint planning, standups, and retrospectives with the engineering team
• Present product direction and delivery status to senior leadership and board members
• Define acceptance criteria and validate that delivered features meet investor needs
• Monitor competitor products and industry trends in real estate fintech

What we're looking for:

• 3+ years in a Product Owner, Product Manager, or similar role at a SaaS or fintech company
• Strong understanding of real estate investing, property management, or real estate finance (direct investing experience is a major plus)
• Experience working with distributed or international engineering teams across time zones
• Comfortable presenting to and collaborating with C-suite executives and board members
• Familiarity with agile/scrum methodologies and tools (Jira, Linear, or similar)
• Excellent written and verbal communication — you'll be the translator between business language and technical requirements
• Bonus: experience with accounting systems, general ledger concepts, or tax preparation workflows
• Bonus: familiarity with AI/ML product features and how to write requirements for AI-driven functionality

Compensation: Competitive salary + equity. This is a key early hire — you'll have meaningful ownership in the company.

Location: Remote, with preference for candidates located east of the Denver time zone (Central or Eastern time) to maximize overlap with both our US-based leadership (Sarasota, FL) and our Moldova-based engineering team (EET/UTC+2).

RealBooks is hiring a Chief Revenue Officer to own our revenue engine end-to-end — capture, generation, and the go-to-market motion that gets us there. This is a C-level executive role reporting directly to the CEO and working alongside the COO and CIO.

You'll define who we sell to, how we sell, what we charge, and how we capture every dollar of opportunity in the market. You'll build the sales and marketing functions, design the pricing and packaging strategy, and forge the partnerships that put RealBooks in front of every serious real estate investor.

This role is equal parts strategic and hands-on. We're pre-Series A, which means you'll be building the revenue playbook from scratch, not inheriting one.

What you'll do:

Revenue capture

• Own the closing motion — build, hire, and lead the sales function from first AE through a full team
• Build the pipeline-to-close playbook: discovery, demo, qualification, negotiation, and close
• Set and run the forecast — quotas, pacing, win rates, and pipeline coverage
• Drive expansion revenue — upsell, cross-sell, and net revenue retention across the existing customer base

Revenue generation

• Build and lead the marketing function — content, SEO, demand gen, paid acquisition, brand, and lifecycle
• Design and iterate on the pricing and packaging model (Bird Dog, DIY'er, Mogul) to maximize conversion, ARPU, and lifetime value
• Develop the partnership and channel strategy: property managers, title companies, lenders, brokerages, CPA firms, and investor communities (BiggerPockets, local REIAs, podcasts, conferences)
• Stand up the lead-gen engine — events, webinars, content, and community-led growth

Go-to-market strategy

• Define the GTM strategy across all customer segments — individual investors through portfolio operators
• Identify and prioritize target market segments — determine where RealBooks wins first and how we expand
• Own positioning, messaging, and competitive differentiation in the market
• Represent RealBooks at industry conferences, podcasts, webinars, and investor communities
• Report to the CEO and collaborate with the board on revenue strategy, fundraising narrative, and market opportunity sizing
• Define and track revenue KPIs: MRR, ARR, CAC, LTV, churn, win rate, conversion, and pipeline velocity

What we're looking for:

• 7+ years in revenue leadership — CRO, VP Sales, VP Growth, or similar — ideally at a B2B SaaS, fintech, or proptech company
• Proven track record of building revenue from early stage (pre-$1M ARR) through growth phase
• Demonstrated success across the full revenue motion: outbound, inbound, partnerships, and expansion
• Deep understanding of real estate investing, property management, or adjacent industries — you need to speak the investor's language
• Experience designing and iterating on SaaS pricing and packaging
• Strong network in the real estate investment community, proptech ecosystem, or CPA/accounting profession
• Experience hiring, leading, and operating a sales and marketing team — even a lean one
• Comfortable in a startup environment — you'll build the systems and processes, not just manage them
• Experience working with founders and boards on revenue strategy and fundraising
• Bonus: experience with partnership-led growth or channel sales models
• Bonus: experience marketing and selling AI-powered products

Compensation: Competitive base salary + significant equity stake + performance incentives. This is a co-building role — your equity reflects that.

Location: Remote, with preference for candidates east of Denver (Central or Eastern time). Willingness to travel for industry events, partnership meetings, and periodic team gatherings in Sarasota, FL.

This is not a typical ML engineer role. RealBooks is looking for someone who can build production AI systems AND understands how accounting actually works — debits, credits, general ledgers, chart of accounts, depreciation schedules, and tax classification logic.

You'll design and implement the machine learning models that power our Autonomous General Ledger and AI agent architecture (Penny, Dollar Bill, and Uncle Sam). Your models will classify transactions, extract data from receipts and invoices, optimize tax strategies, detect anomalies, and continuously learn from investor behavior — all within a system that must be accurate enough for tax filing and audit defense.

What you'll do:

• Design, train, and deploy ML models for financial transaction classification — mapping bank feed and credit card transactions to the correct GL accounts, properties, and IRS categories
• Build intelligent document processing pipelines for receipt and invoice data extraction (OCR, NLP, structured data extraction from PDFs, images, and email content)
• Develop tax optimization models that identify deductions, depreciation strategies, and cost segregation opportunities across real estate portfolios
• Implement anomaly detection for financial data — flagging misclassified transactions, duplicate entries, and reconciliation discrepancies
• Build and maintain the AI backbone for our three named agents: Penny (expense tracking), Dollar Bill (financial analysis), Uncle Sam (tax strategy)
• Collaborate with the engineering team to deploy models into production with proper monitoring, versioning, and feedback loops
• Work with the Product Owner to translate accounting domain requirements into ML system design
• Continuously improve model accuracy using investor corrections and real-world financial data

What we're looking for:

• 3+ years building production ML/AI systems — not just notebooks, but deployed, monitored, production models
• Strong foundation in NLP, document understanding, or financial ML
• Practical understanding of accounting fundamentals: double-entry bookkeeping, general ledger structure, chart of accounts, journal entries, trial balance, financial statements
• Experience with or strong interest in: real estate accounting, IRS tax categories (Schedule E, depreciation, capital gains), or property-level financial reporting
• Proficiency in Python, with experience in ML frameworks (PyTorch, TensorFlow, scikit-learn, or similar)
• Experience with LLM integration, prompt engineering, or agent architectures is a strong plus
• Familiarity with OCR and document processing tools (Tesseract, AWS Textract, Google Document AI, or similar)
• Comfortable working in a startup where you'll own the full ML lifecycle — from data collection to model deployment to monitoring
• Bonus: CPA, accounting coursework, or professional experience in bookkeeping or tax preparation
• Bonus: experience with real estate financial modeling or property management software

Compensation: Competitive salary + equity. This role is rare — the intersection of ML expertise and accounting domain knowledge — and compensation reflects that.

Location: Remote, with preference for candidates east of Denver (Central or Eastern time) to maximize collaboration with our US-based leadership and Moldova-based engineering team.

RealBooks is hiring a Full-Stack Engineer to build the platform investors trust with their entire financial life. You'll ship features across the stack — frontend, backend, data, and integrations — for a product that has to be polished enough to delight real estate investors and accurate enough to survive an IRS audit.

You'll work alongside our distributed engineering team — leadership in Sarasota, Florida and the core engineering team in Moldova. The work spans everything from the customer-facing web and mobile apps to the integrations that pull in bank feeds, parse receipts and HUD statements, and feed our Autonomous General Ledger.

What you'll do:

• Build customer-facing features across the web app (app.realbooks.io) and the mobile apps (iOS + Android) — TypeScript on the frontend, Python on the backend
• Ship integrations that ingest financial data from every angle: bank feeds, email forwarding (receipts@realbooks.io), receipt OCR, and HUD statement parsing
• Implement and maintain IRS schedule generation (Schedule D, E, F, 8949, 8582, 4562) with the correctness guarantees real estate investors and CPAs need
• Work on the systems that power our AI agents — Penny (expense tracking), Dollar Bill (financial analysis), and Uncle Sam (tax strategy) — building the data pipelines, classification feedback loops, and human-in-the-loop tooling
• Help maintain the multi-entity, multi-property data model that supports investors with complex legal structures (LLCs, trusts, S-Corps)
• Write clean, well-tested code for systems that handle financial data — correctness matters more than cleverness, and nothing ships without tests
• Collaborate across time zones with the engineering team in Moldova; participate in code reviews, design discussions, and shared roadmap planning

What we're looking for:

• 4+ years building production web applications, ideally across both frontend and backend
• Strong TypeScript and Python proficiency
• Experience with relational databases (PostgreSQL preferred) and the schema design that goes with multi-tenant, multi-entity SaaS
• Comfortable with cloud infrastructure (AWS, GCP, or similar) and modern deployment practices — CI/CD, infrastructure-as-code, observability
• Care about correctness — financial systems have no margin for "we'll fix it later"
• Comfortable working asynchronously with a distributed team across multiple time zones
• Bonus: experience with accounting systems, fintech, or real estate technology
• Bonus: experience integrating with banking APIs (Plaid, MX, Finicity) or document-processing services (AWS Textract, Google Document AI, OCR pipelines)
• Bonus: experience shipping AI/ML-powered features in a production setting
• Bonus: mobile experience (React Native, Flutter, or native iOS/Android)

Compensation: Competitive salary + equity. Early-stage hire with meaningful ownership in the company.

Location: Remote, with preference for candidates east of Denver (Central or Eastern time) to maximize overlap with both our US-based leadership and Moldova-based engineering team.

RealBooks is hiring an AI/Machine Learning Engineer to build the ML platform and agent infrastructure behind our three named AI agents — Penny (expense categorization), Dollar Bill (financial analysis), and Uncle Sam (tax strategy).

This is the systems-and-platform side of our AI work. You'll build the training pipelines, model serving, evaluation harnesses, and LLM/agent infrastructure that the team uses to ship intelligence into the product. You'll partner closely with our AI & Accounting Intelligence Engineer (who owns the domain-specific modeling) to make sure the platform is fast, observable, and continuously improving.

The work has to be accurate enough that a CPA can sign off on what comes out of it — millions of bank transactions classified, tens of thousands of receipts extracted, and deductions surfaced at scale.

What you'll do:

• Build and operate the ML platform: training pipelines, model registry, evaluation, deployment, monitoring, and a feedback loop that captures investor corrections and re-trains automatically
• Design and ship agent infrastructure for our LLM-powered features — prompt orchestration, tool use, RAG over financial data, and grounding/safety for an audit-grade product
• Build document-understanding pipelines for receipts, invoices, HUD statements, and forwarded emails — combining OCR, NLP, and structured extraction
• Train and serve transaction-classification models that map bank-feed and credit-card data to GL accounts, properties, and IRS categories
• Implement anomaly-detection systems that flag misclassified transactions, duplicate entries, and reconciliation discrepancies
• Partner with the full-stack team to integrate models end-to-end — model accuracy without good UX is wasted
• Set the standards for ML rigor in a financial product: evaluation, reproducibility, drift monitoring, and human-in-the-loop review

What we're looking for:

• 4+ years building production ML/AI systems — deployed, monitored, and continuously improved (research notebooks alone don't count)
• Strong Python proficiency; experience with PyTorch, TensorFlow, scikit-learn, or HuggingFace
• Hands-on experience with NLP, document understanding, or financial/structured ML
• Practical experience with LLM integration: prompt engineering, RAG, tool use, or agent frameworks (LangChain, LlamaIndex, or custom agent harnesses)
• Familiarity with OCR and document-processing tooling (Tesseract, AWS Textract, Google Document AI, etc.)
• Experience with cloud-based ML infrastructure (SageMaker, Vertex AI, or rolled-your-own on AWS/GCP)
• Strong intuition for evaluation: building eval sets, measuring model quality, and driving continuous improvement
• Comfortable owning the full ML lifecycle in a startup — data, models, deployment, and monitoring
• Bonus: experience building human-in-the-loop systems that learn from user corrections
• Bonus: experience operating LLM/agent systems in production with safety and grounding requirements
• Bonus: any exposure to financial or accounting data

Compensation: Competitive salary + equity. This is a foundational engineering hire — comp reflects that.

Location: Remote, with preference for candidates east of Denver (Central or Eastern time) to maximize collaboration with our US-based leadership and Moldova-based engineering team.

Our users are real estate investors, not accountants. You'll design interfaces that make complex financial data feel simple and actionable — dashboards, mobile receipt capture, tax summaries, and portfolio views. Proficiency in Figma and experience designing for fintech or SaaS preferred.

You'll own the full marketing funnel — content strategy, SEO, social media, paid acquisition, email campaigns, and partnerships with real estate communities. Experience marketing to real estate investors or in B2B SaaS growth is a strong plus.

We're a growing team and we're always looking for exceptional people. If you're passionate about real estate, fintech, or AI and think you'd be a great fit, tell us how you'd contribute.