Head of Deal Desk

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 $4 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 1000+ (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.

We are seeking a strategic and operationally-driven Lead Deal Desk Strategist to be a cornerstone of our commercial success. You will act as the central nervous system for deal execution, partnering closely with Sales, Legal, and Finance to structure, negotiate, and close complex deals. Your primary objective is to accelerate deal velocity while ensuring compliance and maximizing value. This is a high-impact role for a proactive problem-solver who thrives in a fast-paced environment and is passionate about building scalable processes.

What you'll be doing:

• Own the Deal Lifecycle: Serve as the trusted advisor and subject matter expert for the Sales team on deal structuring, pricing, and contract negotiations. You will manage the process from initial quote to final signature;
• Accelerate Sales Cycles: Drive the end-to-end deal process, proactively identifying and removing friction points to increase the velocity of deals moving through the pipeline;
• Master the Quoting Process: Take full ownership of the configure-price-quote (CPQ) process, ensuring all deal structures and quotes are accurate, compliant, and strategically sound;
• Drive Process Excellence: Continuously identify opportunities to streamline and automate deal desk workflows. You will develop and document best practices to build a scalable foundation for a world-class deal desk function;
• Champion AI Integration: Evaluate and implement AI-powered tools to enhance deal analysis, contract review, and process automation, bringing cutting-edge efficiency to our operations;
• Ensure Data Fidelity: Guarantee the absolute integrity of all executed contracts and booking information, ensuring data flows accurately to downstream systems for reliable reporting and forecasting;
• Lead Contract Negotiations: Manage the contract redlining process, collaborating with legal and finance teams to ensure favorable terms that align with company policies and mitigate risk.

What you need to have:

• 7+ years of experience in Deal Desk, Revenue Operations, Sales Operations, or a similar function, preferably within the SaaS or Health technology industry;
• Extensive experience with contract review, redlining, and managing the negotiation process for complex commercial agreements;
• Deep expertise in CRM and CPQ tools (Salesforce experience is highly preferred);
• A strong understanding of SaaS or Health Technology business models, pricing strategies, and revenue recognition principles;
• Proven ability to work cross-functionally and build strong relationships with Sales, Legal, and Finance stakeholders;
• An analytical and process-oriented mindset with a track record of improving and scaling commercial operations.

What we would love to see:

• Experience with contract management tools such as Ironclad;
• Experience with Salesforce.com;
• Experience in Digital Health and/or SaaS industries.

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.

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
• Discretionary vacation
• Snacks and beverages
• English class

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