Andrew Hoag is the founder and CEO of Teampay, an expense management platform. We spoke to Andrew about competitive dynamics in the expense management market, Teampay's GTM strategy, challenges in scaling corporate cards, and selling into the enterprise.

1. What went into starting Teampay? What problem are you solving and what’s the core use case that’s giving Teampay traction?

2. Early on Teampay incorporated a Slack app, something that not many expense management companies have done. What thought went into setting up that integration?

3. How did the Slack and Teams integrations impact the product strategy for Teampay?

4. Are these app integrations your primary go-to-market channel? Or are there other channels that are more important?

5. Teampay has a partnership with Silicon Valley Bank, and Airbase has a partnership with American Express. You mentioned the partnerships help with distribution, but are there other business benefits that you get through these partnerships?

6. What's your process for picking partners for card issuing? What are the key criteria which are important for you, and how do you go about it?

7. In layman’s terms, how does Teampay work?

8. For the end user, the value of Teampay is that it's fast and it’s all done in Teams or in Slack. But from a finance person's perspective, what's the value they derive from Teampay?

9. It seems like your approach is to focus on the product and integrate it into a finance professional's workflow. Can you talk about the benefits or merits of this approach versus something like Bill.com, which is built more on network effects and distribution?

10. Teampay is one of the few companies in this space using a SaaS subscription model instead of monetizing off interchange like Brex or Ramp. How do you compare these two business models and the pros and cons of each approach?

11. Was it a customer-first model that led to your pricing model, or did choosing your pricing model lead to a certain type of customer being attracted toward Teampay?

12. Other companies that are providing corporate cards and expense management solutions are only monetizing through interchange. How do you see the margin profile of these companies evolving or changing as they grow, versus say a SaaS style margin profile that Teampay has?

13. When your customers implement Teampay, what are they typically replacing? Is it other card management and expense management solutions, or is it more Excel and paper/pen based systems?

14. Offering cash back on corporate cards has been a popular tactic. Does Teampay offer cash back? Is that part of your go-to market strategy?

15. Payroll is something most companies still run outside of their expense management systems. Do you see this as a missed opportunity for expense management solutions or even something further down the roadmap?

16. What is the hardest part about building something like Teampay?

17. Given that the workflow engine is what’s driving the product, do you see a difference in the way a mid-market company is using Teampay versus an enterprise company?

18. Since COVID accelerated the rise of remote work, has that had an impact on the way you see your product?

19. How do you see Teampay positioned with respect to companies like Ramp and Brex that started with cards and are now backing into expense management?

20. When it comes to companies like Bill.com and Expensify, which are expense management incumbents, how do you see yourself compared to them? You mentioned that some of your customers actually use those products alongside Teampay.

21. What kind of moat do you think Teampay, or any other company in this space, can develop? Do you think transaction volume could be a moat?

22. What does it take for a company like Teampay to break into enterprises? What are the big challenges that Teampay faced or that other startups will face when they move up market towards enterprise customers?

23. If all goes well, where will Teampay be five years from now?