Joining a health startup as a 1099 contractor can be a great opportunity, but it also comes with unique considerations. Startups can be fast-paced and innovative, but they often lack the structure of larger organizations. Before you sign on, it’s crucial to ask the right questions to ensure you’re protected and the role aligns with your expectations. Here are five topics to bring up during your interview, along with a few practical questions for each.

 

1. Contracting & Compensation

This is the backbone of your working relationship. As a contractor, your pay and responsibilities will likely be defined entirely by the contract, so make sure you fully understand the terms.

Ask:

  1. How is compensation structured? (Flat fee, per encounter, or RVUs?)

  2. Who covers malpractice insurance—me or the company?

  3. What’s the payment schedule, and how are disputes handled?

Why this matters: Without a clear understanding of the financial and legal responsibilities, you could end up with unexpected costs or delays.

 

2. Compliance

Compliance is critical, especially if you’re practicing telemedicine or working across multiple states. A solid compliance process protects your license and ensures the company operates legally.

Ask:

  1. How does the company stay up to date on state and federal regulations?

  2. Do you have a compliance officer or work with an external firm?

  3. Are there systems in place to handle multi-state licensing requirements?

Why this matters: If the startup lacks compliance infrastructure, you could unknowingly end up in risky situations.

 

3. Business Model

You need to understand how the company generates revenue and whether its financial structure is sustainable. This helps you evaluate the long-term viability of your role.

Ask:

  1. What’s the company’s primary revenue stream? (Cash pay, Medicaid, Medicare, private insurance?)

  2. What percentage of revenue depends on physician services?

  3. Are there plans to expand or diversify the business model?

Why this matters: Startups heavily reliant on high-risk or niche services (e.g., controlled substance prescribing) might present more challenges than you’re willing to take on.

 

4. Workflow & Communication

Understanding how the day-to-day operations work is crucial to making sure you’ll have what you need to succeed in the role.

Ask:

  1. What does a typical day look like for contractors in this role?

  2. What tools or platforms are used for communication and task management?

  3. Who do I go to with questions about operations or clinical issues?

Why this matters: Poor communication or disorganized workflows can quickly make your job frustrating and inefficient.

 

5. Technology

Especially in telemedicine, technology plays a huge role in your ability to deliver care and document effectively.

Ask:

  1. What EHR or telemedicine platform do you use?

  2. Is the platform HIPAA-compliant?

  3. What training or support is provided for contractors using your systems?

Why this matters: If the technology is clunky or you’re left to figure it out on your own, it can slow you down and add unnecessary stress.

 

Final Thoughts

Interviewing for a role with a health startup as a 1099 contractor requires a balance of curiosity and caution. You want to understand their operations, revenue, and compliance without overwhelming them with overly detailed questions. By focusing on these five topics and keeping an eye out for red flags, you can make an informed decision about whether the role is a good fit.

Post by: Phoebe GutierrezPhoebe G.
Phoebe is a healthcare policy and regulatory expert and has over 15 years of experience in supporting new and innovative healthcare programs, initiatives and start-ups.

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