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 ContextI 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 buyerThe 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 WithI 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 bolthires, complexity, risk, timing).• Optimize tax outcome for me as the founderIdentify 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 proceedsUS 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 ProfileI 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 TimelineStart date: As soon as possibleLOI / negotiation stage: LOI signed; currently doing due diligenceExpected closing: Likely before end of 2025Please indicate your availability over the next 6 weeks, including any blackout dates. 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). ConfidentialityConfidentiality 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