Director of Customer Success

  • Anywhere

Oversee is revolutionizing how travel is managed. Our automation and ML solutions replace manual processes that result in cost savings and operational efficiency gains. Oversee delivers travel analytics combined with actionable insights for our clients to monitor and improve their travel programs.

We are experiencing exponential revenue growth YoY and work with many of the global FORTUNE 500 companies. If you are looking for a dynamic, fast-paced, and positive work environment and want to be at the core of solving a global $17B problem – Oversee is the place for you!

Candidates located in the East Coast USA and Europe will be considered for this remote position.

We are seeking an experienced Director of Customer Success to lead our CS team. 

As a Director of Customer Success, you will play a pivotal role in our organization, embodying our unwavering commitment to client satisfaction. Your primary responsibility is to cultivate strong, enduring relationships with our clients, optimize our CSM processes, and lead a team.

Your leadership in ensuring client success will not only solidify our existing partnerships but will also pave the way for new opportunities, reinforcing our position as a client-centric organization. You will also be responsible for managing some of our largest revenue clients.

You will report to the CRO while partnering with stakeholders across Sales, Operations, Product, Engineering, and Finance. 

Your Impact:

  • Manage post-sales activity for Enterprise customers through strong relationship-building, product knowledge, planning, and execution
  • Lead, mentor, and inspire the Customer Success team, fostering a culture of excellence, accountability, and continuous improvement. You will have a team of 2-3 direct reports to start off with.
  • Be part of our leadership forum, an assembly of essential stakeholders that partner on the company’s strategy
  • Develop a trusted advisor relationship with customers (high-level executives) to ensure goals are aligned from a business strategy perspective and success metrics are identified
  • Work closely with your Account Executive counterpart to develop a joint success plan for your customers and develop cross-sell and up-sell opportunities
  • Constantly assess “health checks” for your customers to drive satisfaction, adoption, retention, and reduce churn
  • Serve as the ‘voice of the customer’ and provide internal feedback on how we can better serve them to maximize customer value and retention
  • Maintain a deep understanding of our product and speak with customers about the most relevant features/functionality for their specific requirements
  • Increase customer retention and ensure alignment by conducting regular check-in calls and Quarterly & Strategic Business Reviews
  • Work closely with Product and Engineering on identification/tracking of enhancement requests
  • Handle escalations and work across teams to resolve issues
  • Improve upon our existing approaches to customer engagement and account management 


About You:

  • 5+ years of experience in the Corporate Travel industry or travel-related company experience (expense management)
  • 8+ years of experience in Enterprise Customer Success Management
  • 2+ years of experience managing a team
  • Excellent project management and organizational skills in a high-pressure environment, working with high-value customers
  • Able to prioritize tasks and initiatives in a fast-paced environment, as well as problem-solve
  • High energy, go-getter with fresh ideas who takes the initiative to get things done
  • Bachelor’s degree preferred 
  • Experience with CRM systems such as Salesforce and Zendesk.
  • Data-driven, accustomed to analyzing, interpreting, and presenting large data sets. Comparable working with software such as Power BI or a similar tool.
  • Working at a high-growth technology company.
  • Executive-level communication/presenting skills
  • Familiarity / strong passion to work in the business travel technology sector
  • Develop strategies and business plans with partners and execute against metrics and milestones to drive user growth and revenue


  • Leadership experience managing large corporate accounts at a TMC or similar organization
  • Experience working with Power BI
  • Experience working in a startup environment (a company with under 200 employees)


Benefits are an important part of Oversee’s Total Rewards package. This role is eligible for a competitive benefits package that includes medical, dental, vision, a 401(k) plan, paid time off, and much more!

We are dedicated to the development of our team members, firmly believing in their potential for growth. Each team member actively participates in a personalized development plan program designed to nurture their capabilities and propel them toward reaching their fullest potential.

We are committed to equal employment opportunities regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender, gender identity or expression, or veteran status. We are proud to be an equal-opportunity workplace.