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 & Product Officer to own our entire go-to-market motion — from pricing strategy to market positioning to partnerships to revenue growth. This is a C-level executive role reporting directly to the CEO and working alongside the COO and CIO.

You'll define how RealBooks enters the market, who we sell to, what we charge, and how we grow. You'll build and own the revenue engine — sales, marketing, partnerships with real estate trading partners, and strategic alliances with CPAs, property managers, and real estate investment communities.

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

What you'll do:

• Define and execute the go-to-market strategy for RealBooks across all customer segments — from individual investors to portfolio operators
• Own the pricing model — design, test, and iterate on pricing tiers (currently Bird Dog, DIY'er, Mogul) to maximize conversion and revenue
• Identify and prioritize target market segments — determine where RealBooks wins first and how to expand from there
• Build and lead the sales and marketing functions — hire the team, set the targets, run the pipeline
• Develop strategic partnerships with real estate trading partners: property management companies, title companies, lenders, real estate brokerages, CPA firms, and investor communities (BiggerPockets, local REIAs, etc.)
• Work with the Product Owner and engineering team to ensure the product roadmap aligns with market needs and competitive positioning
• Represent RealBooks at industry conferences, podcasts, webinars, and investor communities
• Report to the CEO and collaborate with the board on growth strategy, fundraising narrative, and market opportunity sizing
• Define and track revenue KPIs: MRR, CAC, LTV, churn, conversion rates, and pipeline velocity

What we're looking for:

• 7+ years in revenue, growth, or go-to-market leadership roles — ideally at a B2B SaaS, fintech, or proptech company
• Proven track record of building revenue from early stage (pre-$1M ARR) through growth phase
• 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 models
• Strong network in the real estate investment community, proptech ecosystem, or CPA/accounting profession
• Experience building and managing sales and marketing teams (even small ones — this is an early-stage hire)
• Comfortable in a startup environment — you'll build the systems and processes, not just manage them
• Experience working with founders and boards on strategic direction and fundraising
• Bonus: experience with partnership-led growth or channel sales models
• Bonus: familiarity with AI-powered products and how to position them in market

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.

You'll work across our Astro frontend, Python backend, and cloud infrastructure to ship features that directly impact how real estate investors manage their finances. Comfortable with TypeScript, Python, and modern cloud services. Experience with AI/ML integrations, financial systems, or real estate technology is a plus.

You'll build the intelligence layer — transaction classification, receipt OCR and data extraction, tax optimization models, and financial anomaly detection. Experience with NLP, document understanding, or financial ML is ideal.

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.