Tax Lawyer / Advisor for cross-border SaaS company exit (US C‑Corp, founder in Canada)

Location Preference: Canada or USA (experience with Quebec + US/Delaware is critical) Experience Level: Expert only (10+ similar deals strongly preferred) About Me / Company Context I am the founder and 100% owner of a SaaS startup that is:

• Incorporated as a Delaware C‑Corporation
• Currently valued at approximately USD $2,000,000
• Generating revenue from international customers (primarily SaaS subscriptions)
• At the stage of negotiating a sale with a serious potential buyer

The buyer may acquire either:

• The company (stock/share purchase), or
• The assets of the company (asset purchase)

I am a tax resident of Quebec, Canada (personal tax jurisdiction: Canada / Quebec). My goal is to structure the transaction in a tax-efficient way while remaining fully compliant in all applicable jurisdictions. What I Need Help With I am looking for an experienced tax lawyer / tax advisor with solid cross‑border M&A experience (US–Canada) to:

• Analyze transaction structures
• Compare share sale vs. asset sale from the perspective of:

- My personal tax (Quebec & Canada, and any US exposure) - Corporate tax in the US (Delaware C‑Corp)

• Explain pros and cons of each structure (tax cost, complexity, risk, timing).
• Optimize tax outcome for me as the founder

Identify strategies to minimize total tax burden while remaining compliant.

• Advise on whether it’s preferable for me that the buyer:

- Buys the shares of the Delaware C‑Corp - Or buys assets (IP, customer contracts, codebase, etc.) and how to structure that.

• Consider:

- Canada/Quebec tax treatment of proceeds US withholding/withholding tax issues (if any) Application of Canada–US tax treaty. - Guidance on whether any planning is possible in advance of signing (e.g., holding structures, elections, timing of distributions, etc.) – within realistic constraints given the deal timeline. - Cross‑border tax compliance and reporting

• Outline my reporting obligations in:

- Canada/Quebec - United States (if applicable to me personally)

• Identify any withholding tax obligations for the buyer or for the company.
• Advise on clear documentation and elections that may need to be filed (e.g. with CRA/Revenue Quebec or IRS, if applicable).
• Review of relevant deal documents (tax sections)
• Review term sheet / LOI to flag tax-related issues and suggest changes.
• Provide input on the tax sections of:

- Share Purchase Agreement or Asset Purchase Agreement - Any ancillary documents related to purchase price allocation, earn-outs, etc. - Coordinate with my corporate/M&A lawyer to ensure the tax structure is properly reflected in the legal documents. - Purchase price allocation & post-closing considerations

• Advise on purchase price allocation between assets (if asset deal) in a tax-efficient way.
• Discuss treatment of deferred payments.
• Recommendations for post-closing cash repatriation or winding-down steps (if needed) for the Delaware C‑Corp in a tax‑efficient manner.

This will not replace formal tax filings; I am primarily looking for deal structuring and transaction-level advice to reduce my overall tax burden and avoid costly mistakes. Ideal Candidate Profile I am looking for someone who:

• Is a licensed tax lawyer or senior tax consultant (CPA, tax attorney, or equivalent).
• Has significant experience with cross‑border transactions, specifically:

- Canada–US tax issues - Startup / tech / SaaS exits - Sales of US C‑Corps owned by Canadian residents.

• Has handled multiple deals in the $1M–$20M range (or higher) involving:

- Share vs. asset sale analysis - International owners and buyers - Canada–US tax treaty application.

• Has practical experience dealing with CRA, Revenu Québec, and IRS implications in similar transactions.
• Can communicate clearly and concisely, and is comfortable explaining complex tax concepts in plain language.
• Is available to start immediately and can work within a deal timeline (e.g., drafts and feedback within a few business days).

Deliverables

• Initial diagnostic & recommendations (written + call)
• 60–90 minute call to review:

- My corporate structure - Deal terms (as currently proposed) - My residency and personal tax situation at a high level.

• Followed by a short written memo or structured email covering:

- Recommended deal structure(s) (share vs. asset) - Expected tax consequences in each jurisdiction - Key steps and timelines.

• Detailed tax structuring plan
• Clear outline of:

- Optimal structure from my personal tax perspective - Key clauses and provisions to push for in the LOI/SPA/APA - Any pre-closing steps I should take (if feasible within the timeline).

• Document review and comments
• Written comments on:

- LOI / term sheet - Draft purchase agreement(s) (share or asset) - Any tax-related ancillary documents.

• 1–2 follow-up calls to discuss comments and negotiation strategy.
• High-level guidance on filing and compliance
• A checklist of post-deal tax reporting requirements for me (and for the company if relevant).
• Clarification on when and how to engage a local accountant for filings, if necessary.

Project Timeline Start date: As soon as possible LOI / negotiation stage: LOI signed; currently doing due diligence Expected closing: Likely before end of 2025 Please indicate your availability over the next 6 weeks, including any blackout dates.

How to Apply

When you submit your proposal, please include:

• Jurisdictions where you are qualified (e.g. Quebec/Canada, US (state/federal)).
• Relevant experience
• 2–3 brief examples of similar cross‑border transactions you have worked on, especially:

- Canadian resident founder + US C‑Corp - SaaS or software/tech exits - Structures where share vs. asset deals were compared.

• Your approach

- How you typically structure this kind of advisory engagement. - Whether you work independently or with a team (and who will do the actual work). Confidentiality Confidentiality is essential. I will share more detailed financials and deal terms after an NDA is signed (if you have a standard NDA, I’m happy to use it or provide one). Apply tot his job Apply To this Job