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