At Sword, we’re building AI to heal billions and unlock humanity’s full potential. In doing so, we’re pioneering AI Care, a fundamentally new approach to healthcare built for medical reasoning, safety, and real-time treatment, not generic technology applied after the fact. As both a clinical-centric frontier AI lab and an applied AI platform, Sword is reimagining how care is delivered at scale, removing traditional barriers like appointments, waiting rooms, and stigma so more people can access the care they need—and ultimately get back to lives lived in full.

Since 2020, Sword has expanded across physical therapy, women’s health, cardiometabolic, and mental health, and is now moving beyond the session to a fully AI-native, 24/7 care program that brings physical activity, therapeutic exercise, psychotherapy, nutrition, and behavior change into one connected experience. More than 700,000 members across three continents have completed over 10 million AI sessions, helping 1,000+ enterprise clients avoid more than $1 billion in unnecessary healthcare costs. Backed by 42 clinical studies, 44+ patents, and more than $500 million raised from leading investors including Khosla Ventures, General Catalyst, and Founders Fund, Sword is defining a new standard for healthcare.

AI Proficiency at Sword

AI fluency is a core expectation at Sword. Every candidate is assessed against our three-level framework — be ready to share real examples of how AI is already part of how you work.

• Explorer (Level 1) — Uses AI daily to boost personal productivity

• Builder (Level 2) — Creates workflows and tools that elevate the whole team

• Integrator (Level 3) — Embeds AI into products and processes at scale

Every hire must demonstrate at least Level 1. The expected level will vary depending on the seniority of the role.

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.

• Own the end-to-end RFP, RFI, and proposal response process: intake and qualification, timeline ownership, draft assembly, and on-time submission of high-quality responses

• Coordinate input from Sales, Legal, Finance, Security, and Product subject-matter experts to assemble accurate, persuasive responses, and chase contributors to hit submission deadlines

• Build and maintain a reusable proposal content library - answer bank, boilerplate, case studies, and security/compliance responses - to raise quality and shorten turnaround

• Translate commercial intent into clear pricing, packaging, and SKU guidance within proposals, and route pricing and non-standard terms through the approval matrix before anything is submitted to a customer

• Partner with Sales to tailor proposals to buyer priorities while protecting standard terms, margin, and the integrity of the deal structure

Deal Governance - internal process ownership

You are the gatekeeper between Sales, Finance, and Legal: keeping deals structured, data clean, and process enforced before a contract ever reaches a customer.

• Own CRM data quality and SFDC governance: enforce field completion requirements before deals advance stages, and maintain accurate ownership, split credits, and attribution

• Own the commercial approval matrix and manage approval workflows in CRM and CLM tools (Ironclad, Spotdraft), in partnership with the SFDC admin

• Manage discounting compliance: validate quote configuration and pricing accuracy, route non-standard discount requests for approval, and flag deals requiring executive sign-off

Contract execution - customer-facing orchestration

You are the primary point of contact with customers during the contracting phase - not for legal wording decisions, but to move the deal from agreement to signature.

• Manage the full contract workflow from first draft to countersignature, maintaining the clause library, quote templates, and product catalog

• Negotiate commercial terms directly with customers within approved parameters

• Orchestrate redline reviews: perform the first read on vendor paper, assign review by topic to Legal, Finance, or Risk Management, and ensure deviations from standard MSA/Order Form receive appropriate approval before execution

• Ensure every signed contract reflects the approved deal structure

Systems & continuous improvement

You leave processes better than you found them, and you build the infrastructure that lets a lean team scale.

• Drive continuous improvement of proposal, deal, and contracting processes: identify failure points, document fixes, and enforce adherence across all participants

• Build AI-native tooling with internal teams to meaningfully scale commercial processes, reduce manual effort, and accelerate time-to-close

• Track and analyze deal and proposal patterns to identify bottlenecks and propose data-driven improvements, embedding approved structures back into Salesforce and CPQ

• Maintain and improve deal documentation: approval policies, pricing guidelines, SKU guidance, and process playbooks

What you need to have

Experience

• 3–5 years in a deal desk, commercial contracting, or commercial/sales operations role in a B2B SaaS environment

• Owned RFP/RFI and proposal responses end-to-end: coordinating cross-functional input, managing deadlines, and owning the quality of what reaches the customer

• Managed contract workflows end-to-end: from quote validation and approval routing through redlining, execution, and repository management

• Negotiated commercial terms directly with enterprise customers: payment terms, SLAs, liability positions

• Enforced process and policy discipline across Sales, Legal, and Finance without direct authority over those teams

• Operated within a CLM environment (Ironclad, Spotdraft, or equivalent) and maintained a CRM (Salesforce strongly preferred), with exposure to CPQ tooling, as a system of record for deal data

Skills & Competencies

• Commercial acumen: you understand pricing architecture, deal structures, and how individual contract terms translate to downstream business and financial risk

• Proposal & RFP development: you produce clear, persuasive, well-structured proposals and RFP responses, coordinate SMEs to a deadline, and build reusable content that scales quality across the team

• Contract literacy: you can read and interpret standard MSA and Order Form language, identify non-standard clauses, and know which deviations require Legal vs. Finance vs. executive review

• Customer-facing confidence: you lead redline conversations with enterprise buyers directly, professionally, and without escalating prematurely, you hold the line on approved positions and know when to escalate vs. when to close

• Process discipline: you document what you do, systematize what recurs, flag what breaks, and drive improvement. You leave processes better than you found them

• Automation mindset: you look at a manual process and immediately think about how to reduce it, whether through better tooling, workflow automation, or smarter handoffs

• Written communication: your emails, redline comments, and internal memos are clear, precise, and calibrated to the audience