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Head of Sales – New Initiatives

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 2025, 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.


Sword Health is hiring a Head of Sales to build the commercial engine for our newest business unit focused on mental health. Backed by Sword’s brand and AI Care model, this unit pairs PhD-level psychologists, biometric data, and AI to deliver continuous, personalized care that doesn’t stop when the therapy session ends.And here’s the kicker: pricing is 100% outcome-based. No PMPM. No session fees. Employers only pay when employees complete the program and achieve clinical results.This is a rare opportunity to take a category-defining product to market. You’d be joining early, shaping the playbook, and building the team from the ground up.


We’re looking for someone who can:
  • Open doors with benefits leaders and consultants through existing relationships or creative outreach
  • Sell effectively to enterprise buyers and help shape a winning go-to-market approach
  • Lead and scale a high-performing team with strong coaching and clear direction
 
You don’t need decades of experience or a fancy title - what matters is your ability to demonstrate how you’ll deliver on these outcomes. 

If you're scrappy, strategic, and excited to build something that matters, we want to hear from you.


US - Sword Benefits & Perks:


• Comprehensive health, dental and vision insurance*

• Life and AD&D Insurance*

• Financial advisory services*

• Supplemental Insurance Benefits (Accident, Hospital and Critical Illness)*

• Health Savings Account*

• Equity shares*

• Discretionary PTO plan*

• Parental leave*

• 401(k)

• Flexible working hours

• Remote-first company

• Paid company holidays

• Free digital therapist for you and your family


*Eligibility: Full-time employees regularly working 25+ hours per week


Note: Applicants must have a legal right to work in the United States, and immigration or work visa sponsorship will not be provided.



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 Head of Sales – New Initiatives, Sword Health

Sword Health is on the lookout for a passionate Head of Sales - New Initiatives to drive our mission of freeing two billion people from pain while leading an exciting new business unit focused on mental health. If you've got a knack for opening doors with benefits leaders and thrive in a high-energy environment, this could be the perfect opportunity for you. You'll be part of a company that has revolutionized healthcare using AI Care to provide personalized, outcome-driven care. Your role will involve building a stellar commercial engine where you'll connect with enterprise buyers and help shape a go-to-market strategy that resonates with their needs. At Sword Health, we believe in creating a remarkable work culture that values commitment and energy, and as the Head of Sales, you'll lead a dynamic team to bring our innovative solutions to market. This role isn’t just about making sales; it’s about making a difference and working alongside 900+ talented colleagues who share a common vision. With exceptional benefits like comprehensive health insurance, equity shares, and remote-first flexibility, joining us means becoming part of a mission-focused environment that truly values its employees. If you're scrappy, strategic, and driven by making a real impact, come help us redefine mental health care together.

Frequently Asked Questions (FAQs) for Head of Sales – New Initiatives Role at Sword Health
What are the key responsibilities of the Head of Sales - New Initiatives at Sword Health?

The Head of Sales - New Initiatives at Sword Health will be responsible for building the commercial framework for our mental health business unit. This includes establishing relationships with benefits leaders and enterprise buyers, crafting a winning go-to-market strategy, and leading a high-performing sales team. You’ll also be crucial in ensuring that our innovative, outcome-based pricing model resonates with clients and drives sales.

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What qualifications are needed to apply for the Head of Sales - New Initiatives position at Sword Health?

To be considered for the Head of Sales - New Initiatives role at Sword Health, candidates should have experience in sales, particularly within healthcare or technology sectors. While extensive experience may not be essential, a proven ability to open doors, connect with enterprise buyers, and lead sales strategies is crucial. Additionally, strong communication skills and a passion for innovation in mental health care are highly valued.

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How does Sword Health support its employees in the Head of Sales - New Initiatives role?

At Sword Health, employees in the Head of Sales - New Initiatives role can expect robust support, including comprehensive health, dental, and vision insurance, equity shares, and flexible working hours. Employees also benefit from a remote-first culture, parental leave, financial advisory services, and a discretionary PTO plan, ensuring they have the resources needed to thrive both personally and professionally.

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What is the company culture like at Sword Health for the Head of Sales - New Initiatives?

Sword Health fosters a dynamic and mission-driven company culture, particularly for the Head of Sales - New Initiatives. With a commitment to 'do it for the patients', team members are encouraged to innovate and excel in their roles. Collaboration, support, and passion for improving patient outcomes are key aspects of the culture that make Sword a great place to work.

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What unique opportunities does the Head of Sales - New Initiatives role offer at Sword Health?

The Head of Sales - New Initiatives role at Sword Health offers a unique opportunity to shape a category-defining product in the mental health space. You’ll be involved from the ground up, building a sales team, deciding on strategies, and making a tangible impact on both the company and the lives of individuals seeking mental health support.

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Common Interview Questions for Head of Sales – New Initiatives
How do you approach building relationships with enterprise clients in a sales role?

When building relationships with enterprise clients, I focus on understanding their unique challenges and needs. I believe in proactive communication and providing tailored solutions that can address their concerns. Additionally, leveraging my existing network while creating new connections through outreach can significantly enhance relationship-building.

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What strategies would you implement to create a successful go-to-market plan as the Head of Sales - New Initiatives?

To create a successful go-to-market strategy, I would conduct thorough market research to identify target segments, analyze competitors, and develop value propositions that resonate with potential clients. Collaborating with cross-functional teams, such as marketing and product development, would ensure a cohesive plan that aligns with overall business objectives.

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Can you provide an example of how you've successfully led a sales team in the past?

In my previous role, I successfully led a diverse sales team by establishing clear goals and providing ongoing coaching. I implemented regular training sessions that enhanced skills and motivated the team. Tracking performance metrics allowed us to celebrate successes and identify areas for improvement, creating a high-performing environment.

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What do you think is the biggest challenge in selling healthcare technology solutions?

The biggest challenge in selling healthcare technology solutions often lies in overcoming resistance to change within organizations. Many clients may be hesitant to adopt new technologies due to fear of disruption. To address this, I focus on demonstrating clear ROI and patient outcomes while building trust through transparent communication.

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How do you measure success in a sales leadership role?

Success in a sales leadership role is typically measured through various KPIs like revenue growth, client acquisition rates, and team performance metrics. Additionally, I value feedback from clients and team members as indicators of a healthy sales environment, emphasizing the importance of building long-term relationships and nurturing a positive team culture.

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What motivates you to work in the mental health space?

I am deeply motivated to work in the mental health space because I believe in the transformative power of mental health support and innovation. Having witnessed its impact on individuals and families, I am passionate about bringing effective solutions to market and improving patient experiences through technology.

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How would you handle underperformance in your sales team?

When addressing underperformance, I believe in fostering open communication and identifying any barriers the team member may face. Together, we would set achievable goals and create a supportive plan for improvement, leveraging training resources and ongoing mentorship to lift performance levels.

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Describe your experience with outcome-based pricing models.

I have experience with outcome-based pricing models, which I find to be an innovative approach that aligns payment with results achieved. This model encourages clients to invest in programs that demonstrate efficacy and value, making the sales process more compelling as it shifts the focus to real-world results.

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What role does collaboration play in a successful sales team?

Collaboration plays a crucial role in a successful sales team, as it enhances idea-sharing and resource pooling. Encouraging a culture of collaboration allows team members to learn from one another, optimize strategies, and tackle larger challenges as a cohesive unit, ultimately driving better results.

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How would you ensure your sales approach aligns with Sword Health's mission?

To ensure my sales approach aligns with Sword Health's mission, I would prioritize understanding the core values and goals of the organization. By tying our sales strategies to the overarching mission of improving patient outcomes, I can effectively communicate our value proposition in a way that resonates both internally and externally.

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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 16, 2025

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