Senior Deal Desk Manager

JOB OVERVIEW The Senior Deal Desk Manager is a senior individual contributor role responsible for how Legion prices, structures, approves, and contracts global deals across every region Legion sells into. Reporting to the Head of Revenue Operations, this person will take a Deal Desk that already has a foundation and scale it into a fast, compliant, AI-native function — through better systems and automation, not more headcount. The ideal candidate has built Deal Desk operations from scratch at an early-stage or growth-stage SaaS company and knows what to standardize, what to automate, and what to leave flexible. They work AI-first: when a process is slow, their first move is to build an agent, a tool, or an automation. This person will serve as the connective tissue between Sales, Finance, Legal, and Client Management, helping to streamline quote-to-close workflows, enforce pricing governance, and accelerate revenue realization. RESPONSIBILITIES AND DUTIES • Own deal structuring for complex new business, expansion, and renewal deals, partnering with sales leaders on creative structures that protect margin and policy. • Own the approval matrix, discount guardrails, non-standard terms policy, and SLAs, with accountability for approval cycle time and quote accuracy. • Support global deals end to end, including multi-currency pricing, multiple contracting entities, regional terms and tax considerations, and approval cycles that span time zones. • Partner with Legal and Finance on contract standards, regional contracting requirements (data protection terms, local entity paper, currency/FX policy), revenue recognition alignment, and the order-to-cash handoff. • Design Deal Desk workflows with AI at the core — for example, automated deal pre-screening against pricing and packaging policy, AI-generated deal summaries for approvers, and AI-assisted redline review against Legal’s playbook. • Build and iterate working tools — pricing calculators, quoting tools, and approval automations — using AI-assisted development. • Set guardrails for AI in deal workflows, including human-in-the-loop approvals, appropriate data handling, and a clear audit trail. • Own and evolve Legion’s quoting and contracting stack (CPQ, CLM, DocuSign) with Salesforce as the system of record, including tools built in-house, and ensure workflows handle currencies, entities, and regional templates without manual workarounds. • Develop reporting and dashboards that give Sales, Finance, and executive leadership visibility into discount trends, packaging adherence, approval turnaround times, and the impact of automation. • Present deal analysis and insights directly in executive pricing reviews and forecast discussions. • Partner closely with RevOps, Product Marketing, and Finance to operationalize pricing and packaging changes. Build the deal calculators, edge-case rules, and sales playbooks that bring new pricing to life in the field. REQUIRED SKILLS AND QUALIFICATIONS • • 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. • Demonstrated experience building Deal Desk processes from the ground up at an early-stage or growth-stage company, with the ability to walk through what was built, in what order, and what you would do differently. • Hands-on AI practitioner who has used AI tools (e.g., Claude, ChatGPT, Copilot, Agentforce) to automate real Deal Desk or RevOps work, with an example to share. • Hands-on experience structuring and contracting international SaaS deals across multiple regions, currencies, and legal entities. • Deep expertise in SaaS pricing — subscription, usage-based, consumption-based, and hybrid models — along with discount governance and contracting best practices. • Experience implementing CPQ and CLM systems; strong modeling skills in Excel or Google Sheets. • Proven ability to influence without authority across Sales, Finance, Legal, and executive leadership, including saying no to senior sellers while keeping the relationship intact. PREFERRED QUALIFICATIONS AND ATTRIBUTES • • Experience launching AI, agentic, or data product SKUs, or partner and marketplace deal structures. • Advanced proficiency with Salesforce CRM • Experience in WFM, HCM, or enterprise SaaS selling to retail, hospitality, or healthcare. • Operates with a builder’s mindset — proactive, resourceful, and eager to create clarity from ambiguity with a high degree of independence. • Strong personal ownership, high integrity, and a focus on outcomes over activity. • Ability to balance strategic thinking with hands-on execution. • Thrives in a collaborative, mission-driven environment and embraces change with enthusiasm. • Flexibility to cover urgent deal approvals across time zones, especially at quarter-end. SALARY RANGE: Base Salary Range $100,000 - $140,000 + Bonus + Stock Equity At Legion, we offer competitive compensation and benefits packages to all employees. As a fully remote employer, pay for positions is determined using local, national, and industry-specific survey data. Our posted salary range is done so in good faith based on national data and may be refined for a candidate's region/town/cost of living. We strive to make competitive offers allowing employees room for future growth. Salaries will be based on the applicant’s location, level of experience, education, and specialized knowledge and skills. Additionally, we consider the external market rate, the amount we have budgeted internally, and internal equity within the company for the same position. BACKGROUND AND OPPORTUNITY ABOUT LEGION Join Legion's mission to turn hourly jobs into good jobs. We're a remote, mission-driven team seeking exceptional talent to propel this vision. Embrace a culture that's collaborative, fast-paced, and entrepreneurial. With us, you'll grow your skills, work closely with experienced executives, and contribute significantly to our mission. Our award-winning AI-native workforce management platform is intelligent, automated, and employee-centric and proven to deliver 13x ROI. We help labor-intensive organizations maximize labor efficiency and employee engagement simultaneously. Legion has earned recognition for its innovation, including spots on the Inc. 5000 list, Forbes’ Next Billion Dollar Startups, and awards for our AI technology. Backed by leading investors such as Norwest Venture Partners, Stripes, First Round Capital, XYZ Ventures, Webb Investment Network, Workday Ventures, and NTT DOCOMO Ventures, we're making real change. If you're ready to make an impact and grow your career, Legion is where you belong. Join us in making hourly work rewarding and fulfilling. BACKGROUND AND OPPORTUNITY There are almost 75 million hourly workers in the United States, representing more than half of the entire workforce. Historically, managing hourly employees has been difficult due to high attrition (average of 60%) and high replacement costs (average of $3,200 per employee in retail). The ongoing labor shortage and competition from the gig economy, make it more difficult to attract and retain hourly employees. The top reasons hourly employees leave their jobs are a lack of schedule empowerment, poor communication with employers, and an inability to get paid early. Gen Z and the millennial workforce demand gig-like flexibility, modern technology, and compelling work options. Legion’s mission is to turn hourly jobs into good jobs, serving the hourly workers who make up the majority of the US workforce. We believe in empowering employees and helping employers be efficient and innovative by enabling intelligent automation powered by Legion’s Workforce Management platform to optimize labor efficiency and enhance the employee experience simultaneously. Legion WFM was built for the cloud with AI at the core and is designed to handle the complexity of modern businesses and meet the needs of today’s hourly employees. Our team is composed of dedicated individuals from all backgrounds and experiences, globally distributed across all time zones. For more information, visit https://legion.co COMPENSATION & BENEFITS At Legion, we offer competitive compensation and benefits packages to all employees. As a fully remote employer, pay for positions is determined using local, national, and industry-specific survey data. We strive to make competitive offers allowing employees room for future growth. Salaries will be based on the applicant’s location, level of experience, education, and specialized knowledge and skills. Additionally, we consider the external market rate, the amount we have budgeted internally, and internal equity within the company for the same position. Benefits include, but are not limited to: • Health Benefits • Paid Time Off and Paid Holidays • Parental Leave • Equity • Monthly Wellness Reimbursement • Monthly Lunch on Legion EQUAL EMPLOYMENT OPPORTUNITY Legion Technologies is proud to be an equal opportunity employer and is committed to maintaining a diverse and inclusive work environment. All qualified applicants will be considered for employment without regard to race, color, religion, sex, age, disability, marital status, familial status, sexual orientation, pregnancy, genetic information, gender identity, gender expression, national origin, ancestry, citizenship status, veteran status, and any other legally protected status under federal, state, or local anti-discrimination laws. DISABILITY ACCOMMODATION For individuals with disabilities who need additional assistance at any point in the application and interview process, please email recruiting@legion.co Legion is an equal opportunity employer. All applicants will be considered for employment without attention to race, religion, color, sex, sexual orientation, gender identity, age, national origin, veteran, disability status, or any other basis covered by appropriate law. How We Determine What We Pay As a global employer, Legion determines pay for positions using local, national, and industry-specific survey data. We evaluate external equity and the cost of labor/prevailing wage index in the relative marketplace for jobs directly comparable to jobs within our company. Our posted salary range is based on national data and may be refined for a candidate's region/town/cost of living. For new hires, we strive to make competitive offers allowing the new employee room for future growth. Salaries will be based on the applicant’s location, level of experience, education, and specialized knowledge and skills. Additionally, we consider the external market rate, the amount we have budgeted internally, and internal equity within the company for the same position. An employee/candidate with a stronger skill set will receive higher pay. Job Applicant Privacy Policy This Job Applicant Privacy Policy (“Policy”) describes how Legion Technologies, Inc. (“Legion”, “we”, “us” and “our”) collects, uses, and discloses “personal information” as defined under California law from and about job applicants who are residents of California. This Policy does not apply to our handling of data gathered about you in your role as a user of our consumer-facing services. When you interact with us as in that role, the Legion Privacy Policy applies. • Types of Personal Information We Handle We collect, store, and use various types of personal information through the application and recruitment process. We collect such information either directly from you or (where applicable) from another person or entity, such as an employment agency or consultancy, background check provider, or other referral sources. This information includes: • Identification and contact information, and related identifiers such as full name, date and place of birth, citizenship and permanent residence, home and business addresses, telephone numbers, email addresses, and s…