Real Talk if You’re Looking for a Job at a Health Tech Startup | Out-Of-Pocket

Why It Matters

As health‑tech startups scale, the hiring dynamics shift, making strategic positioning essential for talent to secure meaningful, well‑compensated roles. Employers also benefit from understanding these candidate expectations to attract high‑impact hires.

Key Takeaways

• Remote health‑tech roles face tenfold applicant surge.
• Honest self‑assessment of title vs compensation crucial.
• Strong, articulated opinions differentiate candidates in interviews.
• AI‑enhanced prototypes boost cold‑email response rates.
• Growth‑stage startups offer faster career advancement.

Pulse Analysis

The hiring landscape for health‑tech startups has evolved dramatically. Remote openings now attract a flood of applicants, driving down compensation and increasing the importance of differentiation. Startups are also blurring traditional role boundaries, demanding candidates who can navigate ambiguity, adopt AI‑driven workflows, and contribute across product, sales, and operations. This fluidity forces job seekers to reassess whether they prioritize a prestigious title or a compensation package that aligns with market realities.

For candidates, the article outlines a playbook that begins with honest self‑evaluation. Understanding where you sit on the performance curve helps you target roles that match your skill level and avoid premature promotions that could lead to failure. Demonstrating strong, well‑articulated opinions during interviews signals cultural fit and strategic thinking, while leveraging AI tools—such as building a quick prototype or using LLMs for research—can turn a generic cold email into a compelling pitch. Concrete, company‑specific questions further showcase depth of preparation and a focus on long‑term impact.

Employers in the health‑tech sector must adapt to these candidate expectations. By offering clear growth trajectories, transparent compensation structures, and opportunities to work with cutting‑edge AI tools, startups can attract top talent despite the heightened competition for remote roles. Prioritizing rapid growth not only expands the "pie" for employees but also signals market validation, which is crucial for securing funding and scaling operations. In this environment, the ability to align mission, compensation, and career development will determine which startups secure the talent needed to drive innovation forward.

Real talk if you’re looking for a job at a health tech startup | Out-Of-Pocket

By Nikhil (aka “Thinkboi”) · outofpocket.health

Most times here I talk about healthcare stuff. But every so often I’ll dispense some wisdom that only a 33‑year‑old who hasn’t interviewed for a job in 7 years could.

I’ve been having a lot of conversations with people looking to work at a healthcare startup. Unfortunately it’s clear that no one has had the hard conversation with them about their prospects or approach. So I’ve decided to be your parasocial relationship that’s sitting you down and having a real‑talk convo with you.

This advice is more specific for people looking for jobs at startups. (It assumes you have a safety net and are not in financial dire straits.)

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Do you want a job that makes you look cool to friends, or makes money?

IMO you should be honest with yourself about which of these you care about more. You are likely sacrificing one in pursuit of the other.

• People often optimize for titles that look good on LinkedIn, even if the role duties and compensation are identical to a less‑flashy title.

• Choosing a company because of a “mission” can attract many applicants but may also make it harder for the company to generate revenue, which can suppress compensation.

• Good salespeople are highly valued at startups; many product managers would be better off in sales.

Be honest about your priorities and recognize that cooler‑sounding jobs are usually harder to get.

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You should be opinionated

Holding back opinions in an interview can hurt you in two ways:

1. You blend in with every other candidate and are hard to remember.

2. You may accept a role that conflicts with your core beliefs, leading to misery.

Having strong, well‑articulated opinions helps you stand out and can guide you toward a better fit. Some areas to form opinions about:

• Which products or features should be expanded or killed?

• How would you implement a process, tool, or staffing model differently?

• What cultural values are essential for a startup, even if they’re unpopular?

• What trade‑offs should be made in a given scenario?

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Are you actually good at your job?

Understanding where you rank on the performance curve matters:

1. You might be aiming for a level you’re not ready for, setting yourself up for failure.

2. Different startup stages suit different work styles; some need structure, others thrive on ambiguity.

3. References and back‑channel checks have become crucial—someone needs to vouch for you.

4. If you’re below the 50th percentile, consider building a complementary skill set (e.g., AI tools, content creation, sales) to become rarer.

Seek honest feedback from mentors or trusted peers, or use AI tools with the right prompts to self‑assess.

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Remote roles will have 10× the competition

Remote positions attract many more applicants than hybrid or in‑person roles, which can depress compensation and increase the risk of outsourcing. Remember that the remote‑work landscape is not the same as the COVID‑era environment.

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Clinician reality check

• Very few opportunities exist for doctors to “dedicate a few hours a month” to a startup unless you’re a well‑known name.

• Competition among doctors with startup experience is fierce; lack of experience makes it harder to sell yourself.

• Understand basic healthcare business models before interviewing.

• Startup compensation differs dramatically from traditional clinical pay; you’ll need to negotiate cash, equity, and role responsibilities.

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Write an actually good cold email

1. Mention something specific about the company or person and give your take or reaction.

2. Bonus: Build a tiny prototype related to your point.

3. Ask a concrete request rather than a vague “let’s chat.”

4. Follow up—persistence matters.

5. Use AI for research, not for drafting the email; people can tell when it’s AI‑generated.

Even if a company isn’t hiring, reaching out can keep you top‑of‑mind for future openings.

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A bunch of job postings online aren’t real

Many listings are posted solely for compliance or to build a future pipeline. Be aware that some “openings” are placeholders.

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Featured jobs

Morgan Health – Health Care Analytics Engineer

(New York City, NY; Boston, MA; or Washington, D.C.)

Looking for someone to design data warehouses, work with dbt, and build user‑centric solutions.

MediCircle – Director of Medication Donation Growth

(New York, NY or Sugar Land/Houston Metro Area)

Lead the growth of a medication donation program by forming strategic partnerships and activating donor communities.

Liza Health – Strategy & Ops

(Cambridge, MA)

Early‑career generalist role (2‑5 years experience) in a high‑growth environment; focus on analytics and operations.

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You should be playing with AI tools

Startups expect you to leverage AI for productivity beyond simple copy‑and‑paste. Try tools like Claude Code, NotebookLM, Zapier AI, n8n, or Replit. Even a basic task‑tracker built with an LLM demonstrates agency and self‑starting ability.

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Ask company‑specific questions during the interview

Instead of generic queries, ask pointed questions such as:

• “What was the hardest part of rolling out the recent product announcement?”

• “How does the cultural value X you mentioned manifest day‑to‑day?”

• “If I succeed in this role, how might the responsibilities evolve in two years?”

Understanding the company’s revenue model and ROI pitch is also essential; inability to articulate this is a red flag.

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Growth is the cure to all ailments

When you have the luxury to choose, favor companies that are growing rapidly. Fast growth creates internal opportunities, new responsibilities, and a larger “pie” for everyone.

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Conclusion – the rules have changed

• Roles are becoming more fluid, making it harder to match candidates to job descriptions.

• Resume padding is so common that employers assume exaggeration unless proven otherwise.

• Leverage now heavily favors employers; they can be highly selective.

The hiring game has shifted. Recognize these changes, adapt your strategy, and good luck out there.

Thinkboi out,

Nikhil (aka “Just get a job? Why don’t I strap on my job helmet and fire into job land?”)

Twitter: @nikillinit Instagram: @outofpockethealth Other posts: outofpocket.health/posts