Principal Executive Recruiter

We are looking for a Principal Recruiter that will serve as a trusted strategic partner to Transcarent’s most senior leaders. This role is designed for a proven executive recruiter who thrives at the intersection of strategy, influence, and execution. You will own and evolve our approach to hiring senior leaders, VP and above level talent, while shaping the future leadership bench that powers Transcarent’s mission.

You will operate with a high degree of autonomy, partner deeply with executive leadership, and bring market insight, rigor, and best-in-class practices to every search. This is not a transactional recruiting role; it is a consultative, high-impact position critical to the company’s growth and long-term success.

What You’ll Do

Executive & Leadership Search Ownership

• Lead end-to-end executive and senior leadership searches across all functions, from role definition through offer close and onboarding partnership.

• Design and execute tailored search strategies for complex, confidential, and high-impact leadership roles.

• Build leadership teams from the ground up in support of new products, offerings, and strategic initiatives.

Strategic Partnership & Advisory

• Serve as a trusted talent advisor to executives and senior leaders, influencing role design, succession planning, and long-term workforce strategy.

• Partner closely with hiring leaders, HRBPs, and Compensation to align on talent needs, leveling, compensation strategy, and closing approaches.

• Coach executives on selection best practices, interview design, bias mitigation, and effective decision-making.

Market Intelligence & Thought Leadership

• Conduct deep market research and competitive analysis to provide real-time intelligence on leadership talent pools, compensation trends, and hiring dynamics.

• Translate data and insights into actionable recommendations that shape hiring strategies and outcomes.

• Continuously refine Transcarent’s executive hiring approach using industry best practices and emerging trends.

Offer Strategy & Closing Excellence

• Lead complex offer strategy, negotiation, and closing discussions with executive candidates.

• Partner with leaders to balance business needs, market realities, and candidate motivations to secure top-tier talent.

Process Excellence & Continuous Improvement

• Ensure exceptional candidate and stakeholder experience throughout the executive hiring lifecycle.

• Maintain rigorous documentation, feedback, and compliance within the applicant tracking system.

• Identify opportunities to streamline, evolve, and scale executive recruiting processes.

• Participate in and lead Talent Acquisition initiatives and projects of high complexity and visibility.

What We’re Looking For

• 10+ years of recruiting experience, with significant focus on executive and senior leadership hiring (VP+), ideally in technology, healthcare, science, or high-growth environments.

• Demonstrated success leading complex, high-stakes, and confidential executive searches.

• Strong executive presence with the ability to influence, challenge, and partner credibly with senior leaders.

• Deep expertise in sourcing, assessment, interview strategy, and selection for leadership roles.

• Exceptional interpersonal, consulting, and negotiation skills; comfortable navigating ambiguity and competing priorities.

• Proven ability to operate independently while managing multiple critical searches simultaneously.

• Experience leveraging applicant tracking systems and talent analytics to inform decisions.

• Strong business acumen with the ability to quickly understand products, services, and organizational strategy.

• Passion for building diverse leadership teams and advancing inclusive hiring practices.

As a remote position, the salary range for this role is:
$150,000—$175,000 USD

Who we are

Transcarent and Accolade have come together to create the One Place for Health and Care, the leading personalized health and care experience that delivers unmatched choice, quality, and outcomes. Transcarent’s AI-powered WayFinding, comprehensive Care Experiences – Cancer Care, Surgery Care, Weight – and Pharmacy Benefits offerings combined with Accolade’s health advocacy, expert medical opinion, and primary care, allows us to meet people wherever they are on their health and care journey. Together, more than 20 million people have access to the combined company’s offerings. Employers, health plans, and leading point solutions rely on us to provide trusted information, increase access, and deliver care.

We are looking for teammates to join us in building our company, culture, and Member experience who:

• Put people first, and make decisions with the Member’s best interests in mind

• Are active learners, constantly looking to improve and grow

• Are driven by our mission to measurably improve health and care each day

• Bring the energy needed to transform health and care, and move and adapt rapidly

• Are laser focused on delivering results for Members, and proactively problem solving to get there

Total Rewards

Individual compensation packages are based on a few different factors unique to each candidate, including primary work location and an evaluation of a candidate’s skills, experience, market demands, and internal equity.

Salary is just one component of Transcarent's total package. All regular employees are also eligible for the corporate bonus program or a sales incentive (target included in OTE) as well as stock options.

Our benefits and perks programs include, but are not limited to:

• Competitive medical, dental, and vision coverage

• Competitive 401(k) Plan with a generous company match

• Flexible Time Off/Paid Time Off, 12 paid holidays

• Protection Plans including Life Insurance, Disability Insurance, and Supplemental Insurance

• Mental Health and Wellness benefits

Transcarent is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. If you are a person with a disability and require assistance during the application process, please don’t hesitate to reach out!

Research shows that candidates from underrepresented backgrounds often don’t apply unless they meet 100% of the job criteria. While we have worked to consolidate the minimum qualifications for each role, we aren’t looking for someone who checks each box on a page; we’re looking for active learners and people who care about disrupting the current health and care with their unique experiences.