Building Your A-Team: The Art and Science of Hiring Technical Talent in Healthcare

“What makes technical hiring so unique and critical in healthtech?”

The answer lies at the intersection of opportunity, impact, and culture. Healthtech requires a unique blend of technical expertise, domain knowledge, and alignment with a mission-driven purpose. This session will explore how to build hiring strategies that attract, assess, and retain the best technical talent for healthtech organizations.

Session Objectives

1. Deciding When to Hire: Understand when top technical talent or a “10x engineer” is necessary for your team.

2. Building a Process: Define the steps to attract, evaluate, and onboard technical hires specific to healthtech needs.

3. Avoiding Pitfalls: Identify common mistakes in hiring and how to avoid them.

4. Creating Alignment: Ensure technical hires align with your mission, values, and company goals.

Agenda

1. Introduction and Personal Anecdote

2. When Do You Need a 10x Engineer?

• Scenarios where they are critical.

• Situations where they are unnecessary.

3. Interactive Role-Play Prompts

• Evaluate different hiring scenarios for

healthtech.

4. The Hiring Journey

• Job descriptions.

• Sourcing candidates.

• Screening and deep-dive interviews.

5. Trial Period

• How to implement and evaluate trial periods in

healthtech.

6. Closing and Onboarding

• Personalizing offers.

• Structured onboarding with patient-centered

goals.

7. Avoiding Pitfalls: Management vs. Technical Excellence

8. Reflections and Q&A

Talking Point: Personal Anecdote

After spending my summer internships at Microsoft, a tech giant with every resource and opportunity at my fingertips, I made what some might call a surprising decision — I chose to work for a stealth AI healthcare startup. It was a company so under-the-radar that my parents, both brown Indian doctors who valued stability and prestige, were understandably skeptical. They wanted to be supportive of my dreams but couldn’t even find a website for this startup. This was years before AI became the buzzword it is today. To them, it looked like I was jumping from a solid career path into the unknown.

But here’s the thing — what that startup lacked in visibility, it more than made up for in its vision and the opportunity it offered me to be part of something groundbreaking. The founders painted a compelling picture of the impact we could have in healthcare. They highlighted the autonomy I would have, the opportunity to own major pieces of the technical stack, and how my contributions would directly shape the company’s future. That combination of mission, opportunity, and trust convinced me to take the leap.

Now, years later, I’m on the other side of the table, building teams and hiring technical talent for my own company. I find myself asking a lot of the same questions: How do we convince someone to join us, especially when we’re not a household name? How do we attract the kind of talent that can build transformative technology in healthcare?

It’s also made me reflect on that decision I made early in my career — what was it about that stealth AI startup that made me say yes? And how do I create a similar pull for top-tier technical talent today?

When do you need a 10x engineer?

Before we even talk about hiring a 10x engineer, we should scope and understand when to even hire a 10x engineer.

Talking Point: Scenarios Where “10x Engineers” Are Critical

1. Building Complex, High-Stakes Systems

• Examples: AI/ML for clinical diagnostics, telehealth platforms, or FDA-compliant software for patient monitoring.

• Why They’re Needed: These systems often require deep expertise and the ability to architect solutions that are scalable, secure, and reliable from the ground up. A 10x engineer can make foundational decisions that prevent costly redesigns later.

• What to Look For: Candidates with a proven track record of delivering high-complexity projects, expertise in niche technologies, and an ability to think long-term about scalability and maintainability. I will probably differ from most here — I think prior healthtech experience is nice to have, but not necessary.

2. Prototyping in Resource-Constrained Environments

• Examples: Early-stage startups or intrapreneurship projects within larger companies.

• Why They’re Needed: When time and resources are limited, a 10x engineer can rapidly prototype and iterate, building MVPs that validate ideas while balancing speed and quality. They often bridge multiple disciplines (e.g., backend, frontend, DevOps).

• What to Look For: Engineers who thrive in ambiguity, are highly independent, and can make trade-offs between short-term deliverables and long-term scalability.

3. Setting Technical Culture and Mentoring Others in an Early-Stage Team

• Examples: Founding technical hires or senior engineers in startups. Early hires at a startup where patient impact and security are paramount.

• Why They’re Needed: Early-stage hires often define the technical culture and processes for the entire company. Early-stage teams need leaders who can build a culture of compliance and innovation while mentoring others. A strong engineer can establish best practices, mentor junior hires, and set the tone for how technology is approached.

• What to Look For: Candidates who not only excel technically but also demonstrate strong communication and leadership skills, as they’ll influence the team’s trajectory beyond code.

Talking Point: When You Don’t Need 10x Engineers

1. Well-Established Systems with Clear Processes

• Examples: Examples: Maintenance of an EMR system or scaling existing SaaS healthtech platforms.

• Why You Don’t Need Them: These roles often require execution within existing frameworks, where collaborative problem-solving and adherence to process are more valuable than individual brilliance. Over-engineering or innovating in these contexts can actually slow down progress.

• What to Look For: Engineers who excel in teamwork, process adherence, and delivering predictable results without constant oversight.

2. Teams Needing Collaborative Problem-Solving Over Technical Brilliance

• Examples: Large organizations where projects require coordination across multiple teams or stakeholders.

• Why You Don’t Need Them: The success of these projects often hinges on communication, collaboration, and alignment, not the ability of one person to solve every technical challenge. A 10x engineer in these settings might struggle to adapt to slower, consensus-driven decision-making processes. I think big tech does a good job of promoting 10x engineers by creating a separate individual contributor track to promote 10x engineers. In startups, promotions can often come with a management role.

• What to Look For: Candidates with strong interpersonal skills, experience working in cross-functional teams, and a knack for breaking down silos.

Activity: Role-Play Prompts

1. “You’re the CTO of a startup launching a healthcare product in a highly regulated market. You have limited funding and need to decide:

• Hire a senior 10x engineer at a premium salary?

• Hire two mid-level engineers who might need more guidance?

1. Think about a current or past technical role you’ve hired for (or been hired into). Was it a scenario where you needed a 10x engineer? Why or why not?
2. Here are three scenarios. Raise your hand if you think you’d need a 10x engineer in each case:

1. Scaling an existing SaaS product with minimal downtime.

2. Building an MVP of a complex AI system in 3 months.

3. Joining a mature team to enhance an established feature set.

Rubric

Use this rubric to evaluate whether hiring a 10x engineer is necessary for your specific healthtech project or company stage. Score each criterion on a scale of 1 (low relevance) to 5 (high relevance) to determine overall need.

1. Project Complexity

• Does the project involve building a high-stakes, complex system?

Examples: AI/ML for clinical decision support, FDA-compliant software, or real-time patient engagement.

☐ 1: Simple project with minimal technical depth.

☐ 3: Moderate complexity; some innovative technical solutions needed.

☐ 5: Highly complex; requires expertise in cutting-edge technology and scalability.

• Are there significant scalability or security challenges?

Examples: Handling large datasets like EHRs or ensuring HIPAA compliance.

☐ 1: Minimal scalability/security requirements.

☐ 3: Some scalability/security considerations.

☐ 5: Requires robust, enterprise-grade scalability and airtight security protocols.

2. Innovation and Prototyping Needs

• Do you need rapid prototyping in a resource-constrained environment?

Examples: MVP development for investor demos or pilot studies in clinical settings.

☐ 1: No, the project has a relaxed timeline with abundant resources.

☐ 3: Yes, but only for certain features or subsystems.

☐ 5: Absolutely; quick iterations are critical to validate the business model.

• Does the project require technical innovation or creating a novel solution?

Examples: Integrating new AI models with FHIR-compliant systems.

☐ 1: No, leveraging existing solutions is sufficient.

☐ 3: Some innovation required but within established frameworks.

☐ 5: Yes, entirely new approaches or technologies are necessary.

3. Organizational Stage

• Is your company/team in the early stages?

Examples: Pre-seed startups, small healthtech teams.

☐ 1: Established company with mature processes.

☐ 3: Growth-stage company; some foundational work remains.

☐ 5: Early-stage; foundational technical decisions still being made.

• Do you need someone to define technical culture and processes?

Examples: Creating coding standards, infrastructure, or compliance workflows.

☐ 1: No, existing team or external experts already manage this.

☐ 3: Partially; improvement of existing processes is needed.

☐ 5: Yes, foundational technical culture needs to be built.

4. Team Dynamics and Resources

• Do you need an independent problem-solver?

Examples: Limited team size with minimal mentorship capacity.

☐ 1: Team is collaborative with strong mentorship available.

☐ 3: Mixed team where some autonomy is needed.

☐ 5: Team lacks bandwidth; self-starters are essential.

• Do you have the budget to hire a 10x engineer?

Examples: Competitive salary, equity options, or benefits for top talent.

☐ 1: Budget constraints prevent offering competitive compensation.

☐ 3: Budget allows for a slightly above-market hire.

☐ 5: Resources available to attract top-tier talent.

5. Domain-Specific Considerations

• Is domain expertise (e.g., healthcare regulations, FHIR/HL7) critical for success?

Examples: Building an EHR-integrated app or FDA-regulated software.

☐ 1: No, general technical expertise suffices.

☐ 3: Some domain-specific knowledge required.

☐ 5: Deep healthcare domain expertise is essential.

• Does the project require bridging healthcare and technology?

Examples: Building tools that integrate clinical workflows with tech solutions.

☐ 1: No, purely technical focus.

☐ 3: Moderate integration with healthcare processes.

☐ 5: Yes, strong understanding of healthcare systems and user needs is critical.

Scoring

• Total up your score across all criteria.

• 10–20: A 10x engineer is likely unnecessary; focus on building a strong, collaborative team.

• 21–35: You may need a highly skilled engineer, but consider hiring a mix of mid-level and senior engineers instead.

• 36–50: Your project or company could significantly benefit from a 10x engineer. Invest in identifying and attracting top talent.

The Hiring Journey

Talking Point: Job Descriptions

• “Must-haves”: Essential technical skills, required experience, critical certifications.

• “Nice-to-haves”: Preferred skills or domain familiarity.

• Best Practice: Work closely with stakeholders to prevent over-specifying and excluding great candidates.

• Be mindful of any biases

Activity: Group collaborates to revise a job description

(example)

Talking Point: Source Candidates

Use a variety of channels:

• General platforms: LinkedIn, Indeed.

• Niche communities: GitHub, Kaggle, HackerRank, or university networks.

• Employee referrals and targeted outreach.

Tailor outreach to highlight unique aspects of your company:

• Impact of the role.

• Growth opportunities.

• Collaborative team culture.

• Pro Tip: Use personalized messaging when reaching out to passive candidates to stand out.

Activity: Discuss best sourcing techniques

Without relying only on referrals

Discussion point: Screen Candidates

• What are folks’ current processes? What’s worked? What hasn’t?
• How do you run an interview now that AI tools are ubiquitous?
• Should you use a technical Screen to standardize challenges or real-world mini-projects to assess problem-solving skills? Will 10x engineers even take a technical screen

Talking point: Examples of technical screens

• For a front-end developer, provide a task to debug and improve a pre-written component.
• Example from Turmerik: https://docs.google.com/document/d/1NffZQsrurA8FyBgQ0D4y4Aw_titK45JmnAhjQ3KD8as/edit?tab=t.0

Discussion: Deep-Dive Interviews

• Role-specific assessments:

• Live coding (for programming roles).

• System design challenges (for architects).

• Evaluate alignment with company values through scenario-based questions.

• Tip: Include future teammates in interviews to assess collaboration dynamics.

Talking Point: Trial Period

How to Implement a Trial Period

1. Define Objectives and Scope

• Set clear goals for the trial period.

• Specify what success looks like for the candidate and the company.

• Example: For a Backend Engineer, success might involve delivering a functional API endpoint or integrating with an existing database system.

2. Structure the Trial Period

• Typical durations range from a few weeks to 90 days, depending on the role and complexity of tasks.

• Decide on the format:

• Freelance or contract-to-hire: Candidates work on a defined project for a set period.

• Probationary period: A full-time hire is contingent on performance during the initial months.

3. Provide Resources and Support

• Ensure the candidate has access to tools, documentation, and team members needed for success.

• Assign a mentor or buddy to guide them and answer questions.

4. Evaluate Progress

• Use measurable outcomes to assess success:

• Technical deliverables (e.g., completed projects, bug fixes).

• Collaboration and communication with the team.

• Alignment with company values and work style.

Benefits of Trial Periods

For Employers:

• Reduce the risk of mis-hires by observing candidates in action.

• Gain insights into how the candidate handles challenges and integrates into the team.

For Candidates:

• Opportunity to evaluate the company’s culture, workflows, and management style.

• Build confidence in their decision to join the organization.

Discussion: Trial Period

I will prepare a 2 week scoped Trial Period technical project. Point out how I scoped it. Point out what to evaluate the candidate on.

Talking Point: Close and Onboard

Crafting Offers:

• Personalize offers based on candidate priorities (e.g., remote work, salary, equity).

• Clearly outline growth opportunities and team impact.

Onboarding Plan:

• Provide structured 30-, 60-, and 90-day goals.

• Assign a buddy or mentor to guide the new hire.

• Handout: Provide a sample onboarding plan for attendees to take away.

Avoiding Pitfalls and Lessons Learned: Management vs. Technical Excellence

Talking Points

1. 10x Engineers Are Not Always 10x Managers

• Many top engineers thrive on solving complex problems and may lack the interest or skills needed to lead and develop a team.

• Forcing a transition to management can lead to dissatisfaction or even attrition.

2. Separate Career Tracks

• Highlight the importance of dual career tracks:

• Technical Leadership: Roles like Principal Engineer or Architect allow growth in technical expertise.

• Management Leadership: Roles like Engineering Manager focus on team building and operational execution.

• Emphasize that organizations should reward both paths equally to retain top talent.

3. Assessing Management Potential

• Evaluate leadership qualities separately from technical skills. Look for:

• Communication and empathy.

• Delegation and mentorship abilities.

• Alignment with team and organizational goals.

Key Takeaway

• Not every 10x engineer should — or wants to — become a manager. Organizations must provide growth opportunities that align with individual strengths and career goals.

Activity

• Prompt: “What happens when your best technical talent becomes a manager? Is this always the right move?”

• Activity: Ask attendees to share examples of when a highly technical hire transitioned into management. Discuss what worked, what didn’t, and why.