About this role.
Legion is seeking an Enterprise Account Executive to generate and close net-new enterprise SaaS business in an East-region named-account territory. The role owns the full sales lifecycle, from executive prospecting and account strategy through business-case development, negotiation, forecasting, and close. Candidates need 3–5 years of enterprise technology sales experience, a strong hunter mindset, and demonstrated success closing $1M ARR deals against a $2M+ annual quota. Workforce management or HCM software experience is preferred, particularly with retail, hospitality, distribution, warehouse, or healthcare customers. This is a remote, fast-paced startup role requiring strong cross-functional collaboration and executive-level communication.
Role DNA
A quick view of the complexity, pace, ownership and collaboration implied by the job description.
Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader US market for similar roles.
Core skills
Skills and capabilities most closely associated with this opportunity.
Sample interview questions
I would segment accounts by industry fit, workforce complexity, strategic triggers, and probable buying capacity. I would map executive stakeholders and influencers, develop account-specific hypotheses around business outcomes, and run coordinated outreach using research, referrals, events, and marketing assets. I would inspect pipeline coverage and conversion data weekly to focus activity on the highest-potential opportunities.
I would explain the customer problem, stakeholder map, competitive context, and sales plan used to create alignment. I would highlight how I established mutual action plans, quantified value, addressed risk and procurement requirements, and maintained executive sponsorship. I would conclude with the commercial result and lessons applied to future deals.
I start by baselining the customer's labor costs, scheduling inefficiencies, overtime, compliance exposure, employee turnover, and manager time spent on manual processes. I translate improvements into measurable financial and employee-experience outcomes, validate assumptions with the customer, and present a conservative, transparent business case. The ROI narrative should connect operational users, finance leaders, and executive decision makers around shared priorities.
I would avoid challenging the statement prematurely and instead ask what outcomes the existing platform delivers well and where gaps remain. I would explore changes in labor strategy, employee expectations, forecasting needs, automation, and reporting that may create a reason to evaluate alternatives. If a meaningful gap exists, I would position a focused value hypothesis and agree on objective evaluation criteria.
I use clear stage definitions tied to verifiable buyer actions, documented next steps, stakeholder access, business-case validation, and commercial progress. I regularly inspect deal risks, close-plan gaps, and historical conversion patterns rather than relying on optimism. I communicate changes early, maintain clean Salesforce data, and pair an accurate commit forecast with a separate upside plan.
Enterprise Account Executive – East
Remote, United States
JOB OVERVIEW
The mission of the Account Executive, Enterprise is to source, develop, and close net new revenue within a named account territory consisting of enterprise prospect accounts headquartered in North America. This role requires a thoughtful, proactive hunter with a well established rolodex and deep industry expertise, to prospect, qualify and close new business. This role is perfect for an enterprise salesperson who can source net new customers and execute with passion, drive, and strong business acumen.
RESPONSIBILITIES AND DUTIES
- Develop a GTM sales strategy to build and grow Legion’s market leadership and achieve business targets
- Understand client needs and align strategy
- Build relationships with decision makers and stakeholders across target client base and participate in closing strategic opportunities when needed
- Play a critical role in business planning, working closely with other senior executives to develop plans, resource requirements, and influence long-term business strategy
- Work cross-functionally with sales leaders, marketing, and product teams to achieve and exceed company revenue targets
- Close deals with enterprises and exceeding revenue targets
- Develop granular account-level strategies to communicate Legion’s unique value proposition
- Leverage industry expertise and Rolodex to build a pipeline of executive-level enterprise opportunities
- Lead a deal through the entire sales lifecycle by building relationships and collaborating with key external and internal stakeholders
- Craft a compelling business justification and ROI for each opportunity
- Maintain accurate and timely customer, pipeline, and forecast data in Salesforce CRM
REQUIRED SKILLS AND QUALIFICATIONS
- 3-5 years of enterprise technology sales experience
- Experience closing $1M ARR new business deals against a $2M+ annual quota
- Strong application SaaS sales background
- Superior negotiation, written, and verbal communication skills
- A mix of large and small company experience. Early stage startup experience highly desired
- Experience selling a Workforce Management (WFM) or Human Capital Management (HCM) software solution strongly preferred
- Experience selling in the Retail, Hospitality, Distribution, Warehouse, and Healthcare industries is a plus
PREFERRED QUALIFICATIONS AND ATTRIBUTES
- Experience selling a Workforce Management (WFM) or Human Capital Management (HCM) software solution
- Experience selling in the Retail, Hospitality, Distribution, Warehouse, and Healthcare industries
- Proactive and able to command respect through intelligence, hard work, and persistence
- Personal passion and fervor for industry-leading next generation technology
- Ability to operate in an environment with limited
- A great communicator who can distill powerful messages which resonate with customers
- Track record of building positive relationships with peers
- Continuous and thoughtful listener, able to learn from customers and leverage input
- Strong personal work ethic focused on high priority issues; action and results oriented
- Unquestionable integrity, credibility, and character; demonstrated high moral and ethical behavior
COMPENSATION & BENEFITS
Salary Range: Base Salary Range $135,000.00 – $185,000 + Commission + 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.
Benefits include, but are not limited to:
- $0 monthly premium and other flexible medical, dental, and vision plans effective on the first day of employment
- 401k plan
- Discretionary Paid Time Off and Paid Holidays
- Parental Leave
- Equity
- Monthly Wellness Reimbursement
- Monthly Lunch on Legion
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 has 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 designed to handle the complexity of modern businesses and meet the needs of today’s hourly employees. Our team is comprised of dedicated individuals from all backgrounds and experiences, globally distributed across all time zones.
For more information, visit https://legion.co
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 such information about your beneficiaries or emergency contacts.
- Professional or employment-related information, including:
- Recruitment, employment, or engagement information such as application forms and information included in a resume, cover letter, or otherwise provided through any application or engagement process; and copies of identification documents, such as driver’s licenses, passports, and visas; and background screening results and references.
- Career information such as job titles; work history; work dates and work locations; information about skills, qualifications, experience, publications, speaking engagements, and preferences; and professional memberships
- Education Information such as institutions attended, degrees, certifications, training courses, publications, and transcript information.
- Legally protected classification information such as race, sex/gender, religious/ philosophical beliefs, gender identity/expression, sexual orientation, marital status, military service, nationality, ethnicity, request for family care leave, political opinions, and criminal history.
- Other information such as any information you voluntarily choose to provide in connection with your job application.
How We Use Personal Information
We collect, use, share, and store personal information from job applicants for our and our service providers’ business and operational purposes in the recruitment process such as: processing your application, tracking your application through the recruitment process, contacting references with your authorization, conducting background checks you authorize, and making hiring decisions. We will also use job applicant information for internal analysis purposes to understand the applicants who apply and to improve our recruitment process. We may sometimes need to use applicant information for legal purposes, such as in connection with any challenges made to our hiring decisions.
With Whom We Share Personal Information
We will disclose job applicant personal information to the following types of entities or in the following circumstances (where applicable):
- Internally: to other Legion personnel involved in the recruiting and hiring process.
- Vendors: such as technology service providers, travel management providers, human resources suppliers, background check companies, and employment agencies or recruiters, where applicable.
- Legal Compliance: when required to do so by law, regulation, or court order or in response to a request for assistance by the police or other law enforcement agency.
- Litigation Purposes: to seek legal advice from our external lawyers or in connection with litigation with a third party.
- Business Transaction Purposes: in connection with the sale, purchase, or merger.
- How to Contact Us About this Policy – If you have any questions about this Policy, please contact privacy@legion.co.
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