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Chief of Staff - New AI Initiative

Sword Health is on a mission to free two billion people from pain. 


With 67% of members achieving a pain-free life and a 70% reduction in surgery intent, at Sword, we are using AI Care to change lives, and save millions for our 25,000+ enterprise clients across three continents. Today, we hold the majority of industry patents, win 70% of competitive evaluations, and have raised more than $300 million from top venture firms like Founders Fund, Sapphire Ventures, General Catalyst, and Khosla Ventures.


Recognized as a Forbes Best Startup Employer in 2024, this award highlights our focus on being a destination for the best and brightest  talent. Not only have we experienced unprecedented growth since our market debut in 2020,  but we’ve also created a remarkable mission and value-driven environment that is loved by our growing team. With a recent valuation of $3 billion, we are in a phase of hyper growth and expansion, and we’re looking for individuals with passion, commitment, and energy to help us scale our global impact. 


Joining Sword means committing to a set of core values, chief amongst them to “do it for the patients” every day, and to always “deliver more than expected” on behalf of our members and clients.


This is an opportunity for you to make a significant difference on a massive scale as you work alongside 900+ (and growing!) talented colleagues, spanning three continents. Your charge? To help us build a pain-free world, powered by AI, enhanced by people — accessible to all.



The new initiative This new initiative is a dynamic startup division within Sword Health's broader portfolio, expanding our AI-driven tools beyond pain management to tackle bigger healthcare challenges. As a startup within our established organization, this venture comes with all the exciting unknowns, rapid iteration, and entrepreneurial opportunities you'd expect from a ground-floor operation. You'll help shape this division from its earliest stages while benefiting from Sword Health's existing infrastructure and expertise.


As Chief of Staff, you'll be at the heart of Sword Health’s new AI initiative designed to combat provider burnout through intelligent automation. Your role? Keep everything and everyone moving in sync to ensure execution at the highest level. You’ll anticipate roadblocks before they appear, cut through complexity, and make sure we stay focused on what matters most.

If you thrive in ambiguity, know how to turn vision into action, and want to be part of something that’s growing fast, this is your chance to make a massive impact.


Important: While ideally this role should be based in Portugal, we will consider exceptional candidates from elsewhere in Europe.


What you’ll be doing:
  • Drive cross-functional projects, from new customer implementations to crafting a new pricing structure, ensuring nothing stalls.
  • Support leadership in decision-making, communication, and execution across key priorities.
  • Spearhead transparency and alignment across teams so that information flows smoothly, and priorities stay clear.
  • Integrate large new teams into our division seamlessly, unifying culture, systems, and workflows while maintaining operational momentum.
  • Analyze existing processes, optimize efficiency, and remove friction so we operate at full speed.
  • Develop, track, and improve key performance metrics that drive growth and impact.
  • Help instill Sword’s high-performance mindset as we double our team in 2025.
  • Build deep relationships with customers and partners, understanding the challenges leaders face as they transform their organizations with AI.


What you need to have:
  • 3-5 years of experience in a high-paced environment - whether it’s a startup, consulting, operations, or something entirely different. If you’ve thrived in a fast-moving, ever-changing setting, you’ll fit right in.
  • A bias for action - you move fast, solve problems on the fly, and don’t wait for permission to make an impact.
  • Hunger and curiosity - you ask the right questions, dig deep, and never settle for surface-level thinking.
  • Exceptional problem-solving skills - you see challenges before they happen and find solutions that drive real results.
  • Strong communication - clear, direct, and confident in both spoken and written English.
  • High emotional intelligence - you navigate different perspectives, align teams, and keep things moving forward.
  • The ability to manage multiple priorities without missing a beat.
  • A strategic mindset with an eye for execution - you connect the big picture to day-to-day operations.


What we would love to see:
  • An entrepreneurial spirit - you take ownership, think creatively, and thrive in ambiguity.
  • Strong communication skills - you can clearly and confidently engage with stakeholders at all levels, structuring information in a way that drives action.
  • A natural relationship-builder - you earn trust quickly and know how to influence without authority.
  • A Bachelor's degree in Engineering, Economics, Management, or a related field—but we care more about what you’ve done than where you studied.


To ensure you feel good solving a big Human problem, we offer:
  • A stimulating, fast-paced environment with lots of room for creativity;
  • A bright future at a promising high-tech startup company;
  • Career development and growth, with a competitive salary;
  • The opportunity to work with a talented team and to add real value to an innovative solution with the potential to change the future of healthcare;
  • A flexible environment where you can control your hours (remotely) with unlimited vacation;
  • Access to our health and well-being program (digital therapist sessions);
  • Remote or Hybrid work policy. 
  • To get to know more about our Tech Stack, check here.


€54,934 - €76,934 a year
Base: €35,814 - €56,279
Variable: €2,686 - €4,221
Net equity value per year: €16,434

These compensation bands are just the starting point. Once someone joins and proves they’re outlier talent, we adjust quickly to ensure their compensation aligns with their impact.

Our job titles may span more than one career level. Actual pay is determined by skills, qualifications, experience, location, market demand, and other factors. Compensation details listed in this posting reflect the base salary and any potential variable, bonus or sales incentives, and the Company’s estimation of the value of private company stock options, if applicable. The pay range is subject to change, future value of company stock options is not guaranteed, and compensation may be modified in the future. In addition to our total compensation, Sword offers a number of benefits as listed below.

Portugal - Sword Benefits & Perks:


• Health, dental and vision insurance

• Meal allowance

• Equity shares

• Remote work allowance

• Flexible working hours

• Work from home

• Unlimited vacation

• Snacks and beverages

• English class

• Unlimited access to our Learning Platform



Note: Please note that this position does not offer relocation assistance. Candidates must possess a valid EU visa and be based in Portugal.



Sword Health, which includes SWORD Health, Inc. and Sword Health Professionals (consisting of Sword Health Care Providers, P.A., SWORD Health Care Providers of NJ, P.C., SWORD Health Care Physical Therapy Providers of CA, P.C.*) complies with applicable Federal and State civil rights laws and does not discriminate on the basis of Age, Ancestry, Color, Citizenship, Gender, Gender expression, Gender identity, Gender information, Marital status, Medical condition, National origin, Physical or mental disability, Pregnancy, Race, Religion, Caste, Sexual orientation, and Veteran status.

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CEO of Sword Health
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Virgilio Bento
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What You Should Know About Chief of Staff - New AI Initiative, Sword Health

Sword Health is on the hunt for a passionate Chief of Staff to lead our new AI Initiative in Porto, as we strive to liberate two billion people from pain! Our mission is powered by innovative AI solutions, and we have an exciting opportunity for the right person to help shape a dynamic startup division within our robust framework. Imagine rolling up your sleeves and diving into a thriving environment where your instincts for strategy, execution, and relationship-building shine. As Chief of Staff, you will be the backbone of our initiative, making sure all departments move in sync and that our groundbreaking AI tools effectively address healthcare challenges. Your days will be filled with driving cross-functional projects, supporting key leadership decisions, and fostering a culture of transparency. The thrill of tackling provider burnout through intelligent automation lies at the forefront of this initiative, giving you a chance to make a massive impact. We need someone with a vibrant mix of problem-solving skills, emotional intelligence, and an entrepreneurial spirit—someone who thrives in ambiguity and knows how to turn vision into action. If you are an exceptional communicator, unafraid of tackling multiple priorities, and ready to help us revolutionize healthcare while having a little fun along the way, this role is for you. Join our incredible team of over 900 talented professionals who are bound by a commitment to delivering more than expected every single day. Together at Sword Health, let’s build a pain-free world!

Frequently Asked Questions (FAQs) for Chief of Staff - New AI Initiative Role at Sword Health
What are the responsibilities of the Chief of Staff at Sword Health?

As the Chief of Staff at Sword Health, you will have a hand in driving cross-functional projects, supporting leadership in decision-making, and ensuring smooth communication across various teams. Your focus will be on aligning priorities, integrating large teams, and optimizing operational efficiency while maintaining momentum to tackle provider burnout through our AI Initiative.

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What qualifications are needed for the Chief of Staff position at Sword Health?

To be considered for the Chief of Staff role at Sword Health, candidates ideally need 3-5 years of experience in fast-paced environments like startups or consulting. Essential skills include strong problem-solving abilities, exceptional communication, emotional intelligence, and a strategic mindset, as well as a degree in Engineering, Economics, Management, or a related field.

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How is the work culture at Sword Health for the Chief of Staff role?

The work culture at Sword Health for the Chief of Staff is vibrant, innovative, and collaborative. With a focus on personal and professional growth, team members are encouraged to take ownership and engage deeply with their responsibilities as they contribute to building a pain-free world powered by AI.

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What kind of impact can the Chief of Staff expect to make at Sword Health?

The Chief of Staff at Sword Health will have a significant impact by leading initiatives that aim to improve healthcare challenges, specifically provider burnout. By driving strategic projects, optimizing workflows, and embedding a high-performance mindset across the team, you will help create substantial advancements in how we deliver healthcare solutions.

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What growth opportunities does Sword Health offer for the Chief of Staff position?

Sword Health offers ample growth opportunities for the Chief of Staff, including a dynamic working environment filled with creativity, access to career development resources, and a chance to work with talented professionals. As the company expands rapidly, there will be opportunities for personal development and advancement while contributing to critical projects.

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Common Interview Questions for Chief of Staff - New AI Initiative
Can you describe a time when you successfully drove a cross-functional project?

When answering this question, focus on your approach to collaboration, how you kept teams aligned, and the specific results achieved. Share examples that highlight your skills in problem-solving and communication.

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How do you handle ambiguity in a fast-paced environment?

Discuss specific strategies you use to thrive in uncertain situations, such as prioritization, gathering data quickly, and making decisions swiftly. Highlight your comfort level with change and your proactive approach.

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What strategies do you employ to foster clear communication across teams?

Share methods you've used to ensure that information flows efficiently among teams. Mention tools or frameworks that help streamline communication and how you make sure everyone stays on the same page.

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How do you prioritize tasks when faced with multiple deadlines?

Explain your prioritization process, detailing how you evaluate urgency versus importance. Discuss time management techniques and any tools you use to keep track of your responsibilities.

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Can you elaborate on your experience with stakeholder management?

Provide examples of how you've built and maintained relationships with key stakeholders. Discuss how you tailor your communication to meet their needs while aligning with the project goals.

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What methods do you use to analyze and improve operational efficiency?

Talk about specific analytical tools or frameworks you've employed to assess operational processes. Discuss how your improvements have led to quantifiable outcomes and enhanced performance.

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Describe your experience with decision-making in a leadership setting.

Focus on your role in supporting leadership decisions. Provide a specific example where your input was crucial in a decision-making process and the outcomes that followed.

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How do you ensure a culture of transparency within a team?

Discuss initiatives you've launched to promote transparency, such as regular check-ins, open forum discussions, or utilizing tech tools for sharing information. Highlight the benefits of such practices.

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Can you provide an example of how you solved a complex problem?

Share a detailed scenario where you identified a challenging problem, the steps you took to analyze it, and the solutions you implemented that led to successful results.

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What attracts you to the Chief of Staff role at Sword Health?

Articulate your enthusiasm for Sword Health’s mission and how you see your values aligning with the company's culture. Mention specific aspects of the AI Initiative that excite you and what you hope to contribute.

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Sword Health is a healthcare company that aims to free 2 billion people from pain by creating the first and only end-to-end global platform to prevent, manage, and treat pain while saving clients millions in healthcare costs.

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Full-time, remote
DATE POSTED
April 3, 2025

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