Freshlake
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Tax & Financial Diligence

Diligence at the Speed of Deal Flow

The AI-native workspace for M&A due diligence. Convert raw VDR data into normalized schedules, tax exposure analysis, and defensible EBITDA bridges.

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Freshlake

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S
Sentry Capital LP
Search findings...
TK
7
Open Risks
$11.8M
Total Exposure
3High
3Medium
1Low
2Resolved
By Category:
Tax 3Finance 4Other 2
$3.7M ITC Clawback Risk: CCPC Status in Question
Tax

Targetco claimed $3.7M in refundable SR&ED ITCs for FY2022-2024, but shareholder records indicate US parent held >50% voting control since March 2021, disqualifying CCPC status.

Tomer Kaplan
Due Nov 20
$2.6M ARR at Risk: Change of Control Termination
Finance
$1.8M Revenue Overstatement: Recognition Policy
Finance
$1.3M EBITDA Overstatement: R&D Cost Underreported
Finance
$890K Vendor Spend Without Contracts
Other
$340K California Sales Tax Exposure Since 2022
Tax
$70K Post-Close Liability: Option Pool Shortfall
Finance
$45K GST/HST Penalties Settled
Tax
Resolved

GST/HST registration completed Oct 2025. Historical returns filed for Jan 2023 - Sep 2025. CRA penalties of $45K paid Nov 1, 2025. No further amounts owing.

Tomer Kaplan
D&O Insurance Coverage Gap Closed
Other
Resolved

D&O policy with Chubb renewed Nov 15, 2025 with $5M coverage. Retroactive date confirmed to Jan 2021. No gap in coverage during Oct 2025 lapse period.

David Park

Financial • Legal • Tax • Operational

How It Works

From data room to decision

01

Ingest & Normalize

Freshlake turns PDFs, Spreadsheets, and other data from multiple sources into structured data

02

Automated Analysis

AI-assisted workflows to analyze Tax exposures, QoE, risk flags, and more

03

IC-Ready Export

Export IC & client-reports in PPT, XLSX, and PDF formats

Unified data, built in

One-click data processing through direct data uploads and integrations with popular data systems.

Automated Analysis

Generate or review diligence materials automatically, and use assisted tooling to edit and finalize with control.

Enterprise Security

AES-256 encryption at rest and in transit. Tenant-isolated data with no cross-contamination.

Compliance Ready

Complete audit trails, role-based access control, and retention policies. Built for regulated environments.

Capabilities

Leverage built-in recipes or build your own

Deal Workflows

Request List Generation

Auto-generate initial and follow-up due diligence request lists tailored to deal context, gaps identified, and workstream priorities.

Freshlake Unified Data

Counsel Communications

Draft seller counsel questions, management interview agendas, and follow-up correspondence with appropriate context.

Freshlake Unified Data

Status Memos & Updates

Generate deal status summaries, workstream updates, and findings memos for internal and client reporting.

Freshlake Unified Data

Disclosure Schedules

Validate or generate disclosure schedules, check completeness of tax and financial disclosures (vendors, customers, contracts), and flag inconsistencies.

Freshlake Unified Data

Tax

Sales Tax & VAT Gaps

Identify registration, remittance, and filing gaps across jurisdictions using CRM data, accounting records, and customer contracts.

CanadaUS

Tax Attribute Summary

Detailed spreadsheet of tax carryforward balances (losses, credits, reserves) extracted from tax returns and validated against tax authority notices and other supporting documentation.

USCanada

Book-to-Tax Reconciliation

Compare tax filings to available financial data, flag unusual adjustments, and generate targeted follow-up requests for supporting schedules.

US GAAPIFRSASPE

Tax Basis Validation

Verify tax cost basis and paid-in capital for shares and capital assets, trace historical adjustments, and validate against supporting schedules.

CanadaUS

PE & Entity Status

Analyze permanent establishment exposure and corporate status eligibility, including shareholder residency and control tests.

CanadaUS

Withholding Tax Compliance

Review cross-border payments for proper withholding, treaty eligibility, and required tax documentation.

Cross-borderTreaty rates

Financial

Quality of Earnings

EBITDA adjustments, normalizations, pro forma analysis with audit trail.

US GAAPIFRSASPE

Working Capital

NWC calculations, peg adjustments, seasonality analysis.

US GAAPIFRSASPE

Revenue Recognition

Accounting standards compliance, contract review, deferred revenue analysis.

US GAAPIFRSASPE

Debt Analysis

Uncover unusual terms in financing facilities, flag potential covenant issues, and identify change of control triggers.

Security Features

AES-256 Encryption
AWS Infrastructure
Tenant Data Isolation
Role-Based Access

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