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Chief of Staff

US - Remote

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 

At Transcarent, we’re transforming how people experience healthcare — and we’re looking for a Chief of Staff to our Chief Commercial Officer (CCO) to help lead the charge. This is a high-impact, highly visible role that sits at the intersection of strategy, execution, and leadership. You’ll be a trusted partner and right hand to the CCO, helping translate vision into action, streamline operations across our commercial teams, and ensure our most important priorities move forward — fast and flawlessly. 

If you’re equal parts strategist, operator, and connector, and you love driving clarity and alignment in complex, fast-paced environments, this role is for you. 

What You’ll Do 

  • Be a strategic thought partner: Work closely with the CCO on business planning, goal setting, and strategic decision-making that drives revenue growth and operational excellence. Serve as an extension of the CCO—acting as a trusted partner and liaison with the CEO’s office to ensure timely, high-quality responses to urgent requests, strategic deal reviews, and executive priorities. 
  • Orchestrate execution: Align cross-functional priorities, track key initiatives, and ensure the right people, resources, and timelines are in place to deliver results. This includes ensuring swift turnaround on needs related to the CEO office. 
  • Run the rhythm of the business: In partnership with Rev Ops, run pipeline and forecast discussions, and leadership team meetings — ensuring clarity, accountability, and follow-through. 
  • Drive communication and alignment: Serve as a bridge between the CCO and leaders across Sales, Marketing, Customer Success, and Operations, ensuring clear and consistent messaging. 
  • Support high-impact initiatives: Partner with Commercial Operations, Marketing, and Finance to define and execute strategic projects that expand pipeline, improve performance, and drive efficiency. 
  • Be AI-centric: Identify and champion opportunities to embed AI across commercial processes—optimizing forecasting, pipeline visibility, customer engagement, and sales productivity to accelerate growth and operational excellence. 
  • Enable effective leadership: Manage internal communications, prepare executive briefings, and help the CCO stay focused on the highest priorities. 
  • Lead through influence: Create structure, anticipate needs, and help remove obstacles for the teams you support — enabling faster, more confident decision-making. 

 

About You 

You’re a purpose-driven operator who thrives at the intersection of strategy and execution. You think several steps ahead, connect the dots across functions, and bring calm, focus, and clarity to fast-moving environments. You know how to lead through influence, and you’re energized by helping teams — and leaders — perform at their best. You also bring: 

  • 10+ years of experience in a strategic, operations, or Chief of Staff role, ideally within a high-growth healthcare, SaaS, or technology organization 
  • Proven success driving cross-functional initiatives that improve efficiency, accountability, and business performance 
  • Strong understanding of commercial strategy and pipeline development — comfortable operating in revenue-driven environments 
  • Excellent communication and executive presence, with the ability to simplify complex ideas and build trust at all levels 
  • Highly organized and detail-oriented, with strong judgment and the ability to prioritize competing demands 
  • Analytical mindset with comfort using data to guide recommendations and measure impact 
  • A collaborative, proactive, and unflappable approach — you anticipate needs, solve problems before they surface, and get things done 
  • Bachelor’s degree required 

 

As a remote position, the salary range for this role is:

$175,000 - $200,000 USD

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  

Location  

You must be authorized to work in the United States. Depending on the position we may have a preference to a specific location, but are generally open to remote work anywhere in the US.  

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. 

 

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