IVP Question Series: Strategy, Fit, and Risk Questions (1 of 3)

Global expansion deals don't fall apart because vendors are bad actors. They fall apart because both sides skip the uncomfortable questions about strategy, fit, and risk until it's too late. I've watched this pattern repeat for two decades: companies waste weeks (sometimes months) trying to shortlist global compliance, EOR, payroll, and entity providers while managing a flood of unsolicited outreach. At the same time, providers chase opportunities that were never a real fit, burning time and resources on deals that go nowhere.

The root problem? Nobody has a clear, practical framework for what "good" actually looks like before the sales cycle begins.

This is Part 1 of a series of questions designed to help CFOs, GCs, and Heads of People build their vendor selection criteria before vendors build their pitch. This first section focuses on Strategy, Fit, and Risk with 11 questions that surface misalignment early, protect both sides from wasting time, and set the foundation for a genuine partnership.

These aren't "gotcha" questions. The best providers I know welcome them because they protect everyone from bad-fit deals that drain resources and damage relationships.

1. EOR vs entity thresholds

"What specific headcount, revenue, or activity thresholds do you use to recommend moving from EOR to a local entity?"

Why this matters: Clarifies when a convenient structure starts to create tax, PE, IP, and banking exposure.

2. Ideal client & fit

"For clients like us, what does your ideal client profile look like in terms of headcount per country, number of entities, and complexity? In which situations are we not an ideal fit?"

Why this matters: Avoids entering a relationship where our needs don't match your model.

3. Proven fit for our profile

"For companies similar to us, can you share a few current clients with a comparable footprint and describe what you deliver for them today?"

Why this matters: Shows whether our use case is familiar and already supported.

4. Where you typically say no

"Which types of clients, countries, or service combinations do you usually decline or refer to other providers?"

Why this matters: Signals clear boundaries around what you can reliably deliver.

5. Churn and reasons for leaving

"For clients that look like us, what is your annual churn rate, and what are the most common reasons those clients decide to move on?"

Why this matters: Surfaces patterns behind relationship breakdowns.

6. Balancing financial and client outcomes

"How do you balance margin or EBITDA targets with client satisfaction and retention when making decisions about pricing, scope, and investment in accounts?"

Why this matters: Shows how you handle trade-offs between financial performance and long-term outcomes.

7. Walk-away criteria

"What internal criteria do you use to decide that an opportunity is not a good fit and you should decline it?"

Why this matters: Vendors with clear 'no' criteria are less likely to over-commit to complex deals.

8. Implementation capacity right now

"Given your current team and project load, how many new multi-country implementations can you realistically take on in the next 3–6 months, and where would we sit in that queue?"

Why this matters: Reduces risk of delays caused by an over-stretched delivery team.

9. Go / no-go checkpoint

"By what stage in your process can you give us a clear yes/no on whether you can support our exact requirements, so we avoid investing months only to discover major gaps?"

Why this matters: Protects both sides from long, low-probability sales cycles.

10. Leadership track record

"Where have your executive and senior leadership team previously worked in this space, and what are the key ways your current operating model differs from those prior organizations?"

Why this matters: Helps distinguish a recycled playbook from a genuinely different approach.

11. Investment in existing clients vs new logos

"Roughly what share of your annual budget goes into improving services and technology for existing clients versus acquiring new clients?"

Why this matters: Indicates whether current customers or new wins receive most attention.

What's Next!

This section focused on Strategy, Fit, and Risk. The next two sections will cover:

• Part 2: Technology, Partners, and Delivery Team

• Part 3: Pricing, Contracts, Governance, and Exit

Each section is designed to be used independently or as part of a complete vendor evaluation framework.