Deal Operations

Sword Health is shifting healthcare from human-first to AI-first through its AI Care platform, making world-class healthcare available anytime, anywhere, while significantly reducing costs for payers, self-insured employers, national health systems, and other healthcare organizations. Sword began by reinventing pain care with AI at its core, and has since expanded into women’s health, movement health, and more recently mental health. Since 2020, more than 700,000 members across three continents have completed 10 million AI sessions, helping Sword’s 1,000+ enterprise clients avoid over $1 billion in unnecessary healthcare costs. Backed by 42 clinical studies and over 44 patents, Sword Health has raised more than $500 million from leading investors, including Khosla Ventures, General Catalyst, Transformation Capital, and Founders Fund. Learn more at www.swordhealth.com.

Role

We are seeking a strategic and operationally-driven Deal Operations manager to be a cornerstone of our commercial success. You will act as the central nervous system for deal execution – partnering closely with Sales, Legal, Finance, and Security to develop winning proposals, structure and negotiate complex deals, and drive them through to signature. Your primary objective is to accelerate deal velocity while balancing speed with control: ensuring compliance, protecting margin, 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.

This is a process leadership role with real authority over how deals move through Sword and a direct line of impact on revenue velocity, contract quality, and cross-functional trust. You will quarterback complex deals end-to-end and, over time, identify and drive improvements to the systems and workflows you operate in – embedding approved deal structures into Salesforce, improving quote configurations, and building the operational infrastructure that lets a lean team support enterprise deal volume at scale.

The role owns the full commercial lifecycle – from proposal and RFP response, through agreement-in-principle, to executed contract. This is a critical function within Commercial Operations that combines proposal development, deal governance, and customer-facing commercial contracting to improve deal velocity and efficiency.

What you’ll be doing

Proposals & RFP response – commercial development

You own how Sword puts its best commercial foot forward: turning customer requirements into accurate, compelling, on-time proposals and RFP responses that reflect Sword’s value and pricing strategy.

• Lead end-to-end RFP and proposal responses for enterprise opportunities, coordinating inputs from Sales, Legal, Finance, Security, and Product
• Build and maintain a proposal content library, pricing templates, and standard response language that can be customized and reused at speed
• Ensure all proposals are accurate, compliant with internal pricing/discount policies, and competitive
• Partner with Sales to understand deal context and tailor commercial framing to customer needs

Deal structuring & governance – deal desk

You are the deal desk: the person Sales comes to when a deal needs structuring, approval, or creative problem-solving under pressure.

• Review and approve non-standard deal terms, discounts, and commercial structures in line with approval matrices
• Partner with Sales to structure complex deals – multi-year, tiered, or non-standard – in ways that are commercially sound and executable
• Ensure deals are properly configured in Salesforce/CPQ with accurate pricing, terms, and required approvals before contracts are issued
• Own the approval workflow: route deals through the right stakeholders efficiently and track outstanding approvals to prevent delays
• Maintain clear deal governance policies and ensure Sales understands and follows them

Contract execution – commercial contracting

You drive contracts from draft to signature – owning the redline process, coordinating Legal and Finance, and keeping deals on track.

• Own the commercial redlining process: manage markups, track open issues, and ensure resolution within acceptable parameters
• Coordinate Legal and Finance review of customer-paper and Sword-paper agreements
• Serve as the primary point of contact for commercial contract negotiations with customers and their procurement teams
• Ensure executed contracts are stored, tracked, and reflected accurately in Salesforce
• Identify recurring contract bottlenecks and work with Legal to pre-approve fallback positions or standard deviations

Systems & process improvement – operational excellence

Over time, you will identify gaps in how deals are structured, approved, and tracked – and fix them.

• Embed standard deal structures, approved terms, and pricing logic into Salesforce/CPQ to reduce manual handling
• Build and maintain dashboards and reporting that give leadership visibility into deal pipeline, approval status, and cycle times
• Document and continuously improve deal desk processes, approval workflows, and contracting playbooks
• Act as a thought partner to Commercial Operations leadership on how to scale deal infrastructure as Sword grows

What we are looking for

• 5+ years in Deal Desk, Sales Operations, Commercial Operations, or a related field – ideally at a B2B SaaS or enterprise software company
• Proven experience managing complex deal cycles end-to-end, including RFP responses, pricing approvals, and contract redlines
• Strong commercial judgment: you understand margin, know when to escalate, and can push back constructively on Sales when needed
• Hands-on experience with Salesforce (CRM) and CPQ tools; familiarity with CLM systems is a plus
• Comfortable working directly with Legal on contract redlines and with Finance on deal economics
• Highly organized and process-driven, with the ability to manage multiple deals simultaneously without dropping threads
• Strong written and verbal communication skills; able to run customer-facing commercial conversations with confidence
• Proactive, low-ego, and collaborative – you get things done without needing the spotlight

What we’d love to see

• Experience building or rebuilding a deal desk function from scratch
• Familiarity with healthcare or digital health commercial models (e.g. PEPM, value-based, risk-sharing)
• Experience with tools like Ironclad, DocuSign, Conga, or similar CLM/e-signature platforms
• Exposure to enterprise procurement processes and customer legal/security review workflows