Remote opportunity at
LegionSenior Deal Desk Manager
Legion is seeking a Senior Deal Desk Manager to handle global pricing, deal structuring, approvals, and contracting across international markets. Operating as a senior individual contributor…
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About This Role
Legion is seeking a Senior Deal Desk Manager to handle global pricing, deal structuring, approvals, and contracting across international markets. Operating as a senior individual contributor reporting to the Head of Revenue Operations, the chosen professional will evolve an existing Deal Desk into an automated, AI-native function. This role serves as a bridge between Sales, Finance, Legal, and Client Management to optimize quote-to-close workflows, maintain margin protection, and expedite revenue…
Job Description
Legion is seeking a Senior Deal Desk Manager to handle global pricing, deal structuring, approvals, and contracting across international markets. Operating as a senior individual contributor reporting to the Head of Revenue Operations, the chosen professional will evolve an existing Deal Desk into an automated, AI-native function. This role serves as a bridge between Sales, Finance, Legal, and Client Management to optimize quote-to-close workflows, maintain margin protection, and expedite revenue realization. The position requires a builder mentality with hands-on technical capabilities to implement tools, pricing calculators, and workflows using artificial intelligence.
Legion offers an award-winning workforce management platform utilizing AI to assist labor-intensive organizations in maximizing efficiency and employee engagement simultaneously. Backed by prominent investors, the company focuses on turning hourly jobs into rewarding opportunities by addressing high turnover and scheduling needs for the domestic hourly workforce.
Responsibilities
- Manage deal structuring for complex renewals, expansions, and new business to safeguard margins and adherence to company policy.
- Oversee the approval matrix, discount limits, service level agreements, and non-standard terms with accountability for quote accuracy and turnaround speed.
- Handle global transactions from start to finish, managing regional terms, multi-currency pricing, tax implications, and multiple contracting entities across time zones.
- Collaborate with Legal and Finance to establish contract standards, order-to-cash handoffs, and revenue recognition alignment.
- Design Deal Desk processes incorporating artificial intelligence for automated screening, summarization, and redline reviews.
- Develop internal utilities including quoting tools, approval automations, and pricing calculators through AI-assisted methods.
- Maintain and improve the quoting and contracting technology stack centered on Salesforce, CPQ, and CLM platforms.
- Produce reporting dashboards providing leadership insights on discount trends, packaging compliance, and approval metrics.
- Partner across departments to operationalize pricing and packaging changes into field-ready playbooks and calculators.
Requirements
- Minimum of 8 years of professional experience in Revenue Operations, Sales Operations, or Deal Desk environments within B2B SaaS companies.
- At least 3 years of direct experience taking ownership of end-to-end Deal Desk operations.
- Demonstrated background establishing Deal Desk workflows from inception at early-stage or growth-stage organizations.
- Practical experience utilizing artificial intelligence tools such as ChatGPT, Claude, Copilot, or Agentforce for operational tasks.
- Hands-on expertise structuring and executing international SaaS contracts across multiple currencies and legal frameworks.
- Comprehensive knowledge of SaaS pricing strategies, subscription structures, usage models, discount governance, and contracting practices.
- Practical background in implementing CPQ and CLM systems alongside advanced spreadsheet modeling abilities.
Qualifications
- Experience bringing AI, agentic, data product SKUs, or partner and marketplace deal structures to market.
- Advanced proficiency using Salesforce CRM.
- Background in workforce management, human capital management, or enterprise software sales targeted at healthcare, retail, or hospitality industries.
Core Skills
Benefits
- Health benefits
- Paid time off and paid holidays
- Parental leave
- Equity
- Monthly wellness reimbursement
- Monthly lunch provided by Legion
Frequently Asked Questions
Answers are based only on the employer’s listing; where it doesn’t say, neither do we.
Is this position remote?
Yes, Legion operates as a fully remote employer.
What is the salary range for this role?
The base salary range is USD 100,000 to 140,000 per year, supplemented by bonus and stock equity.
What level of experience is required?
Candidates must have at least 8 years of experience in Deal Desk, Revenue Operations, or Sales Operations within B2B SaaS companies, including 3 years owning Deal Desk operations end-to-end.
Sample Interview Questions
AI-generated questions tailored to this specific role — a preview of the full practice set.