L

Legion

AI-driven labor forecasting and scheduling

General Counsel

Full-Time
$250k - $300k+ Bonus + Stock equity
Expert
JD
Remote in USA
RemoteSome travel may be required to meet with customers, partners, investors, regulators, and internal teams.
LegalLegal Counsel & Legal Support

About the job

Requirements
  • A J.D. degree from an accredited law school and membership in good standing with at least one U.S. state bar.
  • At least 15 years of combined experience in top-tier law firm and in-house roles, including significant time as General Counsel, Chief Legal Officer, or senior deputy General Counsel at a high-growth technology or SaaS company.
  • Deep experience advising on enterprise SaaS and commercial contracting; corporate governance and venture-backed or private-equity-backed company issues; data privacy and security; and intellectual property strategy and licensing.
  • A demonstrated track record of building and leading legal teams that support rapid growth and international expansion.
  • Ability to operate as a business-minded advisor, balancing risk with strategic and commercial objectives.
  • Exceptional judgment, integrity, and discretion when partnering with executives and the Board.
  • Ability to translate complex legal issues into clear, actionable guidance for non-legal stakeholders.
  • A collaborative, practical, and fast-paced approach to enabling business objectives.
Responsibilities
  • Develop and execute a comprehensive legal strategy aligned with the company’s business objectives and growth plans in AI-powered workforce management.
  • Advise the CEO, executive team, and Board on legal, regulatory, governance, risk, compliance, fundraising, and strategic transaction matters.
  • Build, lead, and mentor an in-house legal team, manage external counsel across specialties and jurisdictions, and establish scalable processes, templates, and playbooks for go-to-market and partnership execution.
  • Serve as corporate secretary for Legion Technologies and its subsidiaries; manage Board and committee governance processes, including agendas, materials, minutes, and consents.
  • Oversee corporate structure, subsidiary management, and global entity compliance.
  • Support equity and debt financings, including investor negotiations, diligence, and compliance with investor rights and governance frameworks.
  • Partner with Finance and People teams on equity plan administration, stock option programs, and related disclosures.
  • Own legal support for commercial operations, including enterprise SaaS subscriptions and professional services agreements; channel, OEM, marketplace, and strategic partner agreements; and data processing, data protection, and information security terms.
  • Work with Sales, Customer Success, and Partnerships to enable predictable deal cycles while managing risk.
  • Partner with Product, Engineering, and Security to ensure the AI-enabled workforce management platform, APIs, and partner integrations comply with applicable laws, industry standards, and customer requirements.
  • Provide product counseling on new features, AI use cases, mobile app capabilities, and international expansion.
  • Own the global privacy and data protection program, including compliance with U.S. federal and state laws such as CCPA/CPRA and applicable international frameworks.
  • Oversee Terms of Service, the privacy policy, and related product policies, keeping them current with regulatory requirements and product capabilities.
  • Work with Security and IT on customer security reviews, audits, and incident response readiness; develop and maintain policies and training on data governance, acceptable use, and ethical AI usage.
  • Advise on workforce employment matters, including hiring, terminations, performance management, compensation, and incentive programs.
  • Support the People team in implementing policies compliant with applicable labor laws and consistent with the company’s mission.
  • Advise Product and Customer Success on features intended to help customers comply with labor and scheduling laws, including predictable scheduling, good-faith estimates, and overtime rules.
  • Develop and implement a global intellectual property strategy covering patents, trademarks, copyrights, trade secrets, and open-source usage.
  • Partner with Product and Engineering to identify and protect innovations involving AI models, algorithms, data pipelines, and workforce management solutions; manage enforcement and defense of intellectual property rights and respond to third-party claims.
  • Monitor legal and regulatory developments affecting AI and machine learning, data privacy and security, employment and labor laws, and enterprise software and cloud services.
  • Design and oversee a risk and compliance framework that includes policies, training, internal controls, and reporting.
  • Support internal investigations and compliance reviews, and partner with HR and other functions on ethics and integrity initiatives.
  • Coordinate with insurers and brokers on coverage such as E&O, cyber, and D&O, and manage claims as needed.
  • Lead legal aspects of M&A, investments, and strategic partnerships from diligence and negotiation through integration; advise on competition, antitrust, and other regulatory considerations for strategic deals.
Desired Qualifications
  • Experience in HR tech, workforce management, fintech, or other data-intensive SaaS businesses.
  • Prior leadership supporting AI/ML products and related ethical, regulatory, and data governance issues.
  • Experience supporting global customers and operations across North America, EMEA, and APAC.
  • Prior work with large enterprise and strategic partners, such as SAP and other HCM vendors.

About the company

L

Legion

View
cbWebsite

Legion.co provides an intelligent automation platform for workforce management tailored to hourly workforces. It uses a proprietary WFM system to forecast demand across locations and automatically generate granular schedules. A self-learning forecasting engine keeps adapting and optimizes scheduling to match business needs with employee skills and preferences. The platform combines manager tools for compliance and engagement with employee features like gig-like flexibility, self-service, earned wage access, and rewards, all under a subscription model.

Company Size

201-500

Company Stage

Late Stage VC

Total Funding

$185.5M

Headquarters

Redwood City, California

Founded

2016

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Simplify's Take

What believers are saying

  • Dollar Tree rolled Legion chainwide across 9,000 stores and 18 distribution centers in 2025.
  • Wilson James chose Legion in March 2026, expanding Legion into UK aviation, security, infrastructure, logistics.
  • Serveo signed Legion in September 2026, validating Spanish expansion and multinational frontline operations.

What critics are saying

  • UKG, Workday, and ADP bundle workforce suites, pressuring Legion's standalone pricing by 2027.
  • Fair-workweek laws raise implementation burden; Legion's compliance promises face scrutiny across jurisdictions in 2026.
  • Retail and hospitality concentration exposes Legion to customer slowdown, churn, and budget cuts during 2026-2027.

What makes Legion unique

  • Legion's AI-native WFM automates forecasting, scheduling, compliance, and employee self-service in one platform.
  • Its Spring 2026 release shipped 90-plus features, including Upper Field Schedule Assistant and safety check-ins.
  • Legion pairs labor optimization with hourly-worker engagement, backed by 2026 Forrester modeling 1,340% ROI.

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Benefits

  • Health Insurance
  • Paid Vacation
  • Paid Holidays
  • Parental Leave
  • Company Equity
  • 401(k) Retirement Plan
  • Monthly Wellness Reimbursement
  • Monthly Lunch on Legion

Growth & Insights and Company News

Headcount

6 month growth

1%

1 year growth

1%

2 year growth

1%
Legion Technologies
Sep 29th, 2026
A leader in WFM today. Building for tomorrow.

A leader in WFM today. Building for tomorrow. September 29, 2026 Workforce management is entering a new era. For years, organizations have relied on WFM technology to forecast demand, optimize schedules, track time, manage compliance and help managers make better labor decisions. Those capabilities remain essential. They are the foundation for controlling labor costs, running efficient operations, and creating a better experience for frontline employees. But AI is creating an opportunity for WFM to do more. The next generation of workforce management will move beyond providing insights and recommendations to taking action. AI agents will be able to complete operational work within each organization's data, policies, permissions, and controls, while managers retain oversight, handle exceptions, and apply judgment where it matters most. That's why Legion's recent independent analyst assessments are so meaningful. These assessments highlight the strength of its WFM capabilities customers need today, and the innovation that will help define what comes next. In the 2026 Gartner(R) Critical Capabilities for Workforce Management (WFM) Technology, Legion was named a Visionary. Digging a little deeper, Legion were third overall in scoring for High-Volume Demand and for Unionized and Highly Regulated Workforces. Gartner also noted Legion's differentiation and leadership in AI Innovation and Frontline Worker Experience. Gartner isn't the only analyst firm recognizing Legion's position. Everest Group, NelsonHall and Nucleus Research named Legion a "Leader" in their recent reports. Everest Group's Workforce Management Products PEAK Matrix(R) Assessment 2026 cited Legion's automated forecasting pipeline and conversational, mobile scheduling assistant. NelsonHall's 2026 Workforce Management NEAT Evaluation pointed to Legion's mature demand forecasting and measurable gains in shift fill rates and reduced absenteeism. Nucleus Research's Workforce Management Technology Value Matrix 2026 highlighted Legion's industry-preconfigured approach and AI-driven innovations. Each analyst firm uses a different methodology, so the consistency across these independent assessments carries weight. Legion believe it reflects the depth of Legion's capabilities and its differentiated approach to the market. For Legion, it is a credible signal that its position is grounded not in any one evaluation or point of view, but in the substance of what Legion has built and the results it delivers for customers. That combination matters. There is tremendous excitement around AI right now, but innovation cannot come at the expense of the fundamentals. Organizations still need accurate forecasts, optimized schedules, reliable time and attendance, effective compliance controls and intuitive employee experiences. They need technology that works across complex operating environments and delivers measurable value. The opportunity now is to build on that foundation. Managers still spend a significant amount of time reviewing exceptions, making corrections, responding to requests, identifying risks and adjusting plans as conditions change. AI agents have the potential to take on more of that operational work, responsibly, transparently and within customer-defined boundaries. That changes the role WFM can play. That is what makes this moment so exciting to me. Legion has an opportunity to expand what workforce management can do, reduce the operational burden on managers and give them more time to focus on the people and decisions where their judgment matters most. The consistency Legion is seeing across independent analyst assessments gives Legion confidence that Legion is on the right path. It is not the finish line, but meaningful validation of the progress Legion has made and the opportunity ahead. I'm excited to keep building toward that transformation and to expand the value workforce management can create for operational efficiency, employee experience and the managers at the center of both. Thank you to its customers for trusting Legion with some of their most important workforce challenges, and to the Legion team for continuing to innovate with purpose. There's much more ahead, and I'm excited about what Legion'll build together. Want to hear more from Legion? Sign up to receive the latest industry research, expert-led webinars, and practical WFM resources. Ready for a demo? See how Legion's WFM Software enables intelligent automation to help you maximize labor efficiency and employee engagement simultaneously.

MyTeamTask
Aug 21st, 2026
Team management news: 89% of frontline workers had a shift changed with almost no warning.

Team management news: 89% of frontline workers had a shift changed with almost no warning. If you think of last-minute schedule changes as a minor inconvenience for your team, a new industry report suggests you are underestimating the problem badly. Nearly nine out of ten frontline workers say it happened to them in just the past three months, and the researchers behind the data are tying that instability directly to turnover costs businesses can measure in the millions. What the new data shows. The Frontline Workforce Index 2026, published by Legion in partnership with Retail Economics, surveyed 2,000 frontline retail and hospitality employees and found that 89% had a shift changed or cancelled with less than 48 hours notice in the past three months. The research, based on fieldwork from April 2026, scores overall frontline workforce health at 65 out of 100, which the report describes as a credible baseline with clear operational strain underneath it. The category breakdown is telling. Fairness and Transparency scored a relatively strong 72, and Flexibility and Autonomy scored 69. Schedule Stability and Predictability was the weakest pillar in the entire index. In other words, workers do not feel mistreated in the abstract. They feel specifically unable to count on the schedule they were given, and that gap is where the report says the real damage is happening. The financial numbers back that up. The researchers estimate roughly 320,000 retail and hospitality workers are underemployed relative to the hours they actually want, representing about £0.9 billion in earnings left on the table from better balancing labor capacity. Separately, the report puts total replacement cost exposure tied to workforce instability at £6.7 billion, split between £5.1 billion in training costs for replacement hires and £1.6 billion in lost efficiency while new staff get up to speed. This particular study surveyed UK retail and hospitality workers, but the underlying dynamic, unpredictable schedules driving away staff who would otherwise stay, tracks with what US frontline employers have been reporting for years, and it lines up with the growing wave of predictive scheduling and fair workweek laws already moving through US states and cities. Why this is not just a scheduling software problem. It is tempting to read a stat like this and assume the fix is simply better software for building the schedule. That is part of it, but the report's framing points somewhere more specific: the damage comes from the change itself, not just the original schedule. A shift that gets pulled, shortened, or added with a day's notice or less signals to a worker that their time is not something the business plans around carefully. Do that often enough and the worker starts planning around a different employer instead. This matters even more for businesses that cannot simply post a schedule two weeks out and never touch it. Call-outs happen, demand spikes happen, and a manager needs the ability to adjust staffing in real time. The problem the data identifies is not that changes happen. It is how often they happen with no notice, no pattern, and no communication beyond a last-minute text. What managers should do. * Track how often you are changing shifts with short notice, not just whether you are. Most managers can tell you their average headcount. Few can tell you how many shifts changed in the last 30 days with under 48 hours warning. That number is the one worth watching. * Build a real buffer for common disruptions instead of scrambling every time. A short list of staff who have opted into extra or on-call shifts, updated regularly, turns a scramble into a phone call. Reactive scheduling is what produces the short-notice changes workers are reporting. * Separate genuine emergencies from avoidable ones. A sudden illness is unavoidable. A schedule that gets rewritten every week because demand was never forecast well is not. Look honestly at which category is driving most of your changes. * Give workers a way to see and respond to schedule changes instantly, not the next time they check their phone. Part of what makes a late change feel worse is finding out about it too late to do anything with the news. Fast, direct notification does not fix instability, but it reduces the damage of the changes you cannot avoid. * Ask your team directly whether schedule reliability is a problem before it shows up in your turnover numbers. The index shows the gap between how fair a workplace feels overall and how predictable its schedule feels. That gap is invisible until someone asks about it specifically. The bottom line. Frontline businesses have spent a lot of energy this year on pay, flexibility, and recognition as retention levers, and all of that matters. This new data makes the case that predictability of the schedule itself deserves the same attention. Nearly nine in ten workers experiencing a short-notice change in three months is not an edge case. It is close to universal, and the businesses that get ahead of it are the ones treating schedule stability as a metric to manage, not an unavoidable cost of hourly work. How myteamtasks helps. Real-time task and schedule visibility means every team member sees changes the moment they happen instead of finding out secondhand, and managers get a clear record of how often shifts and assignments are actually changing across a location. For businesses running multiple sites, that same visibility makes it easy to spot which locations are creating the most last-minute disruption and address it before it shows up as turnover. Try it for free Ready to run a smoother operation? Turn your checklists into a real system your whole team follows, with photo proof and real-time monitoring.

Associated Press
Jul 14th, 2026
Legion Technologies launches Spring 2026 release with 90+ workforce management features including AI schedule assistant

Legion Technologies has released its Spring 2026 Production Release, featuring over 90 new capabilities across its AI-native workforce management platform for hourly workers. The update introduces the Legion AI Upper Field Schedule Assistant, which helps district and area leaders oversee multiple store locations by surfacing insights and flagging issues across their portfolios. Key features include Employee Safety Management for one-tap safety check-ins, KPI Productivity Metrics that integrate real-time performance data into scheduling decisions, and Access to Hours Notifications supporting Fair Workweek compliance across seven jurisdictions. The release also adds Document Hub for centralised employee document management and expanded global compliance features for European and Chinese markets. The Redwood City-based company has received multiple industry awards for its AI-powered approach to workforce management, including recognition from the Business Intelligence Group and AI Breakthrough Awards.

Business Wire
Apr 8th, 2026
Legion appoints Carolyn Kwon Montgomery as SVP of people to support next growth phase

Legion Technologies has appointed Carolyn Kwon Montgomery as Senior Vice President of People to support its global expansion. Montgomery joins the AI-native workforce management solution provider's executive leadership team with experience building people organisations in high-growth, venture-backed companies. Most recently Chief People Officer at The Black Tux, Montgomery led people strategy for a 500-employee, multi-state workforce. She has previously achieved measurable results including increasing employee engagement by over 20% and reducing voluntary attrition by 40-50% across critical roles. At Legion, Montgomery will focus on evolving company culture, strengthening leadership development, and implementing scalable systems to support global growth. The company aims to maximise labour efficiency whilst improving conditions for hourly workers.

UC Today
Jan 21st, 2026
Legion Partners with Rebus to Bridge the Gap Between Warehouse and Workforce

Legion partners with Rebus to bridge the gap between warehouse and workforce. Legion and Rebus have joined forces to connect real-time warehouse analytics with AI-driven workforce management, giving operators a faster path from insight to action. Legion Technologies and Rebus have announced a partnership that promises to reshape how warehouses manage their workforce. The collaboration brings together Legion's AI-powered workforce management platform with Rebus' real-time warehouse analytics and labor management system, creating an integrated solution that connects operational data directly to labor planning and execution. The integration aims to tackle several pressing warehouse management issues, from employee engagement and schedule predictability to proactive workforce planning and bottleneck detection. By combining Rebus' live operational insights with Legion's automated scheduling capabilities, the solution enables warehouses to align staffing levels dynamically with actual demand, ensuring the right number of workers with the appropriate skills are deployed exactly where and when they're needed. For warehouse operators, this means moving beyond retrospective reporting to predictive, responsive workforce management that adapts to changing conditions as they unfold. Bridging the gap between warehouse insights and workforce action. The Legion-Rebus integration aims to solve a fundamental problem in modern warehouse operations: having access to critical data but lacking the mechanisms to apply it effectively to day-to-day workforce management. As Sanish Mondkar, CEO and founder of Legion, explains, "Today's logistics leaders have unprecedented access to critical warehouse data and insights - the challenge is applying that data to real-time operations." The partnership creates what Mondkar calls "a seamless path from warehouse insight to workforce action." At the heart of the solution is the connection between Rebus' data ecosystem and Legion's AI-powered scheduling and forecasting engine. When Rebus detects changes in warehouse performance metrics, throughput data, or emerging bottlenecks, this information flows directly into Legion's workforce management platform. Legion then processes these signals to automatically adjust schedules, ensuring labor alignment scales with actual demand rather than static forecasts. This real-time synchronization prevents both costly overstaffing and the operational disruptions that occur when warehouses are understaffed. The integration also transforms the employee experience on the warehouse floor. By aligning Rebus' real-time labor data with Legion's automated scheduling, workers gain schedule predictability and empowerment - factors that have become increasingly important for retention and engagement. Combined with workforce self-service features and on-demand pay capabilities accessible through a single mobile application, the solution turns raw warehouse floor data into tangible improvements in work-life balance and financial wellness - crucial advantages in high-turnover industries like warehousing. For workforce planning teams, the partnership enables a more proactive approach to labor management. Historical performance and throughput data from Rebus feed Legion's AI forecasting engine, creating a unified view of the entire operation. This gives management a clearer view of staffing trends and helps them plan budgets that more accurately reflect operational reality. When Rebus identifies bottlenecks by comparing planned work against actual execution, workforce leaders can immediately adjust staffing plans or reassign labor to maintain consistent throughput and prevent disruptions before they cascade through operations. Legion's momentum continues with major product expansion. Legion Technologies has demonstrated strong momentum entering 2026, and the Rebus partnership follows closely on the heels of another major announcement. The company recently unveiled more than 90 new innovations that significantly extend the capabilities of Legion AI. These innovations introduce autonomous workforce decision automation across forecasting, scheduling, time and attendance, and labor optimization. Central to this expansion is a new generation of AI Assistants that move beyond simple conversational interfaces. These assistants perform sophisticated, multidimensional analysis across forecasts, schedules, labor rules, and execution data. They can answer complex questions about why schedules changed, what trade-offs were made during optimization, and how alternative decisions would impact cost, coverage, compliance, and employee experience. The innovation wave also includes advanced labor planning capabilities that enable complex scenario modeling and detailed what-if analysis across demand patterns, labor constraints, and cost targets. These plans maintain a closed loop with real-time execution, continuously adapting forecasts and schedules as conditions change on the ground. Complementing these capabilities are configurable SmartCards that provide managers with personalized, actionable insights, placing the most relevant information directly at their fingertips through customizable layouts and built-in formulas. Building the future of data-driven workforce management. The Rebus partnership and the recent wave of product innovations expand the arsenal Legion Technologies offers enterprises for managing their workforce. By connecting Rebus' analytics and visibility with Legion's workforce management platform, customers can move faster from insight to action, improving labor efficiency while supporting a more flexible, employee-centric workplace. Looking ahead, the integration of real-time warehouse analytics with AI-powered workforce management sets a new standard for what's possible in logistics operations. As warehouses continue to face pressure from volatile demand patterns and the need to improve profitability, solutions that can dynamically align staffing to actual operational conditions in real time will become increasingly valuable.