Director, Customer Success

Legion Technologies

Legion Technologies

Customer Service, Sales & Business Development
Posted on Wednesday, July 3, 2024

Director, Customer Success

Remote, USA


Reporting to the Chief Customer Officer and serving as a key member of Legion’s Customer Success Leadership Team, as the leader of the Customer Success Management function you will have responsibility for managing all aspects of the Customer Success Management function (customer sentiment, account management, customer expansion, and renewal). This is a management role that is focused on rapidly driving time to value, helping our customers solve their labor problems using Legion solutions, maximizing the value they get through partnering with Legion, and ensuring customers are delighted in adopting the software.

This role requires a consultative and holistic approach to the customer lifecycle. This includes providing guidance and leadership through the onboarding process, consistently communicating our value and early identification and resolution of at-risk customers. You will also be leading strategic initiatives to maximize adoption and identify expansion opportunities, retention, and overall customer lifetime value for our customers.

The ideal candidate is an inspiring leader who works with the team to lead from the front and partners closely with cross-functional groups and leadership at Legion to collaborate on innovative solutions for our customers and deliver results that drive down costs and increase value for the business. Additionally, this individual has had experience scaling a CS function in high-growth companies, specifically targeting the mid-market and Enterprise segments.

Who You Are

  • You develop deep relationships from the ability to operate as a strategic second set of eyes, obsesses about your customers and their success.
  • You are an analytical framework thinker with a talent for decomposing problems and generating generalizable solutions.
  • You are an outcome-driven engagement leader who anticipates bottlenecks and gets things done.
  • You can ingest a lot of data and simplify it down to the key story elements that encapsulate the executive synthesis for a given audience.
  • You want to join a dynamic, entrepreneurial environment that requires adaptability and rapid reprioritization.
  • You have a personal passion and fervor for industry-leading next-generation technology.
  • You take pride in your ability to operate in an environment with limited resources.
  • You hold a strong personal work ethic focused on high-priority issues, action and results-oriented.
  • You possess unquestionable integrity, credibility, and character; demonstrated high moral and ethical behavior.

Your Qualifications

  • 10+ years total experience, with 5+ years leading a Customer Success Management function in an enterprise B2B SaaS environment.
  • Experience scaling Customer Success engagement activities while increasing the impact & efficiency.
  • Demonstrated success in building a Customer Success, Renewals, and/or Customer Engagement function focused on creating efficiencies and automating processes for scalability
  • Prior revenue and/or P&L responsibility for a large book of software maintenance or renewal business
  • History of managing complex accounts with multiple stakeholder points of contact, with high customer satisfaction
  • Experience creating 1:1 and 1:many programs that create customer delight throughout the customer journey.
  • Experience motivating customers through a process or organizational change to achieve desired outcomes.
  • Knowledge and experience with Customer Success Management tools (Gainsight, Churnzero, Tatango, etc.) and processes.
  • Experience analyzing and synthesizing data into data-driven stories and presentations; experimental design experience is a plus.
  • Project/engagement management experience; successfully delivering complex projects on time
  • Consistent record of achievement of quota and KPIs and strong organizational, operational and analytical skills
  • Preferred but not Required: Understand the workforce management (WFM) ecosystem in (2+ years exposure); ideally, direct exposure to retail WFM SaaS software

What You’ll Do

Leadership and People Management

  • Lead and scale the Customer Success Management function
  • By a player-coach initially with one or two accounts to learn the business and our customers.
  • Drive operational improvements in collaboration with the Customer Success Operations & Enablement team, which streamline processes, leverages automation, and enables scale
  • Mentor and coach team members, hire and develop key talent, manage high performance, and create an inclusive team culture.
  • Serve as an inspiring leader in the Customer Success organization by keeping up to speed on the latest practices and available tools.
  • Develop and deploy strategies, action plans, and playbooks to improve the customer experience, increase customer retention, and enable account growth


  • Build strong internal partnerships with cross-functional teams inside and beyond the Customer Success Organization, specifically with
    • the Product function where you’ll facilitate information sharing to ensure our features and new releases are driving value for our customers;
    • the Sales function where you’ll facilitate collaboration on customer success plans;
    • the Engineering and Customer Support functions to ensure quick resolution of customer issues.
  • Represent the voice of the customer and influence internal stakeholders by promoting a customer-centric mindset across the organization
  • Participate in process innovation, development, and rollout across the broader Post-Sales team, ultimately driving efficiency and scalability of the team
  • Serve as an escalation point for CSMs and their customers

Customer Relationship Management

  • Build and nurture C-level relationships across accounts to solidify our partnership and commitment to the customer while penetrating the account deeper
  • Serve as point person for a portfolio of multi-stakeholder, mixed industry customers, sometimes owning entire customer relationships
  • Establish high levels of customer partnership and trust, demonstrating a deep understanding of their labor and workforce management strategies
  • Leverage insight into customers to manage expectations and motivate them through unlocking the full potential of Legion's product
  • Support customers through requests, issues, escalations, and feedback
  • Advocate for your customer across Legion, representing them to all internal departments

Adoption Support

  • Drive successful solution adoption, customer value, retention and expansion goals ultimately improving Legion’s customer lifetime value
  • Create evangelists by listening to customers closely and delighting them with our user experience and service
  • Become a product expert in core Legion WFM modules
  • Maintain core product expertise for end users and configuration
  • Grow product knowledge through regular release training
  • Communicate upcoming release themes and dates to the customer

What’s in it for You

  • Experience the excitement of working at and growing with an expanding venture-backed SaaS company where you can make a huge difference
  • Be part of an exceptionally talented team that retains a significant focus on personal and professional development
  • Contribute to and get recognized for a significant period of growth for the business


Salary Range: Base Salary Range: $165,000 - $200,000 + 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.

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


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.


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


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.


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 fully remote 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.

  1. 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.
  2. 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.

  3. 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.
  4. How to Contact Us About this Policy – If you have any questions about this Policy, please contact privacy@legion.co.