Since 2020, Sword has expanded across Musculoskeletal, 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 1 million members across three continents have completed over 15 million AI sessions, helping 2,000+ enterprise clients avoid more than $1 billion in unnecessary healthcare costs. Backed by 59 clinical studies, 43 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.
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