Opportunity

As the Head of Talent at Thoughtful AI, you’ll play a pivotal role in shaping the foundation of our talent strategy during an exciting period of hyper-growth. Your mission will be to design and implement programs that maximize speed to productivity for new hires, ensuring they ramp up on everything Thoughtful AI with efficiency and enthusiasm. You’ll also oversee talent retention, fostering a culture of performance, engagement, and growth.

In this leadership position, you’ll thrive in a fast-paced environment, drawing on your experience in high-performance organizations to build scalable programs that enable Thoughtful AI to onboard and retain top-tier talent. Your expertise in creating high-impact talent initiatives will ensure every new hire feels equipped and inspired to contribute to our mission to fix the U.S. healthcare system.

As a strategic leader, you’ll own the post-hire employee experience, leveraging your creativity and operational acumen to create a culture of excellence. Your leadership will position Thoughtful AI as not just a place to work, but a place to grow and thrive.

Learn more about our Warrior culture.

Key Responsibilities

Build and Lead Talent Onboarding Programs

Design and execute comprehensive onboarding programs that accelerate speed to productivity, embedding new hires into Thoughtful AI’s mission, culture, and operating rhythm.

Drive Talent Retention

Develop and implement strategies to foster a high-performance culture, ensuring employees feel supported, engaged, and inspired to grow within the organization.

Operationalize Scalability

Create scalable onboarding processes that can evolve with the company, ensuring consistency and excellence as we grow rapidly.

Enhance Employee Development

Collaborate with leadership to design and execute talent development initiatives, including training programs, mentorship opportunities, and career pathing.

Act as a Strategic Partner

Partner with department leaders to align onboarding and retention strategies with organizational goals, providing insights and recommendations to enhance team performance.

Foster a Culture of Feedback

Establish mechanisms for gathering and responding to employee feedback, ensuring continuous improvement in the talent experience.

Own Metrics and Analytics

Track and analyze key performance indicators (KPIs) related to onboarding success, employee engagement, and retention, using data to drive continuous improvement.

Be a Cultural Champion

Embody and promote Thoughtful AI’s values, ensuring that our culture remains a competitive advantage as we scale.

Minimum Qualifications

• Bachelor’s Degree in Business, Operations, Finance or a related field, or eight years of equivalent work experience.
• 5+ years of experience in talent management, onboarding, or a related field, with 2+ years in a leadership role.
• Proven track record of success in a hyper-growth technology environment, competitive investment banking, or management consulting organizations, navigating demanding, high-performance cultures.
• Experience designing and implementing onboarding and retention programs that deliver measurable business outcomes.
• Strong project management skills with the ability to manage multiple initiatives simultaneously.
• The ability to host and coordinate regular IRL onboarding sprints (akin to bootcamps) to jumpstart new employee onboarding and ramp-up.

Preferred Qualifications

• Experience scaling talent programs in a technology, investment banking, or management consulting organization.
• Deep understanding of the unique challenges of high-growth environments and how to navigate them.
• A creative problem-solver with a passion for designing innovative talent solutions.
• Proven ability to lead cross-functional teams and drive alignment.
• Strong analytical skills, with the ability to leverage data to inform strategy.

Thoughtful AI Benefits

• Market-leading base salary and bonus.

• Employee stock options.

• Medical, dental, and vision insurance for you and your dependents.

• Three weeks of paid time off per year to recharge and disconnect.