Chestnut & Oak Capital ManagementLaunching a Private Credit Arm:
A Modern Blueprint for Lean Teams
How a forward-looking family office achieved operational excellence and rapid market entry with minimal staffing through Simplyfile's automated document intelligence platform.
Executive Summary
The Challenge
Chestnut & Oak Capital Management, a forward-looking family office specializing in alternative investments, sought to launch a private credit division to diversify its investment strategy and capture attractive yields in the growing private debt market.
Limited staffing resources and operational complexity
Need for automated, scalable workflow
Speed and accuracy requirements
The Solution
Partnering with Simplyfile, Chestnut & Oak rapidly developed a fully digital, end-to-end private credit workflow, enabling it to launch the new private credit arm effectively with the addition of just one dedicated team member.
1 new hire required to fully staff operations
<5 days average deal turnaround time
30+ active deals simultaneously managed
About the Customer
Chestnut & Oak Capital Management
Chestnut & Oak Capital Management is a forward-thinking family office focused on alternative investments and private credit. Known for its disciplined capital allocation and operational rigor, the firm combines deep financial expertise with a modern, technology-first mindset to streamline investment processes and unlock new opportunities.
From Challenge to Outcome
How Simplyfile helped convert operational headaches into lending success.
Challenge
Chestnut & Oak faced a common challenge for boutique financial institutions:
- Limited Staffing Resources: Desire to minimize hiring overhead and operational complexity.
- Operational Efficiency: Need for an automated, low-risk, scalable workflow from deal sourcing through monitoring.
- Speed and Accuracy: Critical to deliver timely underwriting and decision-making without compromising accuracy or risk controls.
Given these constraints, Chestnut & Oak needed a sophisticated solution to compete effectively with larger credit funds, managing deal complexity without building a large internal team.
Why Simplyfile
Chestnut & Oak selected Simplyfile, an advanced document intelligence and financial analytics platform, to serve as the digital backbone of its private credit operations. The solution provided automation across multiple stages:
Automated Deal Screening: Auto-ingests and analyzes initial deal documentation
Streamlined Due Diligence: Extracts and normalizes complex financial data
Digitized Investment Committee: Auto-generated memos with pre-populated analyses
Automated Legal Handling: Parses agreements for compliance confirmation
Real-Time Monitoring: Continuous borrower compliance tracking
The Solution
Simplyfile served as the digital backbone of private credit operations
Solution Overview
Simplyfile's comprehensive automation platform transformed every aspect of Chestnut & Oak's private credit operations:
End-to-End Workflow
From deal screening through portfolio monitoring, every step is automated and integrated.
Intelligent Document Processing
AI-powered extraction and analysis of financial documents, tax returns, and legal agreements.
Risk Management
Automated flagging of inconsistencies, calculation of covenants, and proactive risk identification.
Automated Deal Screening
Auto-ingests and analyzes initial deal documentation, generating standardized financial summaries and auto-populating indicative term sheets within minutes.
Streamlined Due Diligence
Extracts and normalizes complex financial data, identifies inconsistencies, automates EBITDA adjustments, and flags key risks and data discrepancies.
Digitized Investment Committee
Investment committee memos are auto-generated with pre-populated financial analyses, risk indicators, and compliance checklists.
Automated Legal Document Handling
Credit agreements and legal documentation are parsed automatically to confirm compliance with approved terms, reducing manual legal reviews and error rates.
Real-Time Portfolio Monitoring
Continuously monitors borrower compliance and financial health, automating covenant tracking, bank statement ingestion, and proactive risk identification.
The Results
Impressive operational outcomes and rapid market entry
1
Only one new hire required to fully staff operations
<5 Days
Average deal turnaround time from application to approval
100%
Consistency and auditability across the entire portfolio
30+
Active deals simultaneously managed
Customer Testimonial
"Simplyfile enabled us to build a private credit platform far beyond our expectations, practically overnight. We transformed what could have been months of painstaking setup and staffing into weeks of efficient deployment. With Simplyfile, we've scaled our capabilities, minimized operational risk, and gained the agility and sophistication of a much larger institution."
Managing Partner
Chestnut & Oak Capital Management
Conclusion
Chestnut & Oak's successful deployment of Simplyfile underscores the transformative potential of specialized automation in financial services. By embracing Simplyfile's platform, Chestnut & Oak not only established a robust private credit division with remarkable speed and efficiency but also redefined the operational blueprint for boutique firms in the private investment landscape.
Are you ready for a faster, smoother underwriting process?
Discover the smoother, more accurate process that Chestnut & Oak leveraged to scale their private credit operations.