💸Big opportunity: Tax, accounting, and financial back-office workflows are being rewritten in real time through AI-native software and services firms. While a wave of new companies has emerged, I believe we’re still early in the transition, as these systems need to be accurate and outperform both human judgment and expertise.
There is an opportunity to build:
🧠 A Personal CFO for every individual and SMB
Personal tax returns sit at the center of someone’s financial life — touching income, investments, benefits, and major life decisions. This creates an opportunity to build an AI-native, trusted personal accountant that connects to every source of income and expense, delivers year-round intelligence, and evolves from tax prep into proactive wealth and financial advice.
🤖 Digital workers for controllers and finance teams
Finance leaders are under pressure to move from backward-looking reporting to forward-looking insight. Manual work like revenue recognition, month-end close, reconciliation, and tax calculations will increasingly be handled by agents.
The opportunity to build the next generation of accounting and tax solutions that can finally scale with technology, not people, is pressing: nearly 75% of the CPA workforce reached retirement age by 2020, and the number of incoming CPA certifications has declined by 36% over the last decade.
💫 How I'm thinking about stellar teams💫
1. AI-native teams paired with DOMAIN EXPERTISE: The strongest founding teams combine technical talent with direct industry experience of accounting and tax workflows, unpacking edge cases, compliance risk, and practitioner behavior to build trust and adoption.
2. Distribution Strategy: Selling to consumers and SMBs is notoriously hard and expensive, which makes embedded distribution critical. For mid-market and enterprise, defensibility comes from being deeply embedded in core workflows while moving upmarket over time.
3. Access to unique, proprietary data: High-quality tax returns, financial statements, and labeled accounting data are difficult to source and expensive to maintain. Teams that have a path to owning differentiated datasets paired with feedback gain compounding advantages in model performance.
4. Complex cases and judgment calls: As models get better at producing financial recommendations, the real differentiation shifts to handling complex, ambiguous scenarios. Founders must design systems where AI accelerates human judgment, knows when to escalate, and earns trust in high-stakes decisions.
Who are examples of companies in the space already?
@AccordanceAI @Numerico_AI @UseQuanta @truewindai @ArtifactOffcial @digits @numeral @fifteenth_tax
👇Comment tax if you want the full market map!
If you’re a founder building in the space, I’d love to hear from you! 📧 connie@montageventures.com