Tax Compliance AI Quest

March 4, 2025
Tax Compliance AI Quest

Accomplishment

Built an end-to-end AI-driven tax compliance prototype and successfully automated LinkedIn cold outreach through a custom CRM, resulting in multiple polished investor decks, sales materials, and landing pages.

The Problem

Initially targeted SMBs with an AI-powered tax compliance solution, believing the simplicity and cost savings would resonate. However, discovered SMBs typically pay minimal amounts for tax compliance or manage internally without significant pain points. Pivoted to target multinational corporations (MNCs), expecting more substantial budgets and clear pain points but faced significant hurdles due to the need for specialized domain knowledge and robust professional networks.

The Solution

Ultimately decided to shelve the project temporarily, acknowledging critical gaps in domain expertise and networking capabilities essential for penetrating enterprise-level tax compliance markets effectively.

Challenges Leading to Shelving the Project

  • Realized I lacked the necessary domain expertise to convincingly lead conversations with tax professionals, making sales outreach ineffective.
  • Underestimated the significance of industry networks needed to gain traction among MNCs.
  • Found that brute-force tactics, such as cold emails and calls without credibility, yielded minimal progress.

Lessons Learned

  • Recognized the immense value of domain expertise and professional networks, especially when targeting large enterprises.
  • Learned to rapidly validate business assumptions to avoid prolonged commitments to projects with critical flaws, saving significant time and resources.
  • Developed substantial technical skills including knowledge of advanced AI methodologies such as Graph RAG and C-RAG, which will be invaluable in future projects.

Highlights and Key Outputs

This journey provided valuable clarity on the necessity of aligning technical innovation with deep market insights and industry relationships—a lesson I'll carry forward into future ventures.