Director of Operations Strategy

Journey is an early stage insurtech company building new insurance and fleet management solutions for the car sharing economy. We just completed a fundraising round with some of the top financial and strategic investors in the space. Although still pre-launch, we have signed customer agreements and expect to launch pilots with some of the top travel sites in the world, starting in Q3.

The Role

As we build our operational capabilities, this foundational role will have the opportunity to help define and build our solutions and policies from the ground up. This person will take our strategic goals and build and execute a plan to ensure we execute effectively through each transaction, solve all customer problems efficiently, resolve claims expediently, and ensure the transaction economics are sustainable. The role will entail selecting and implementing software solutions, detailed modeling of potential strategies, define product requirements, act as liaison to the engineering team, and building and monitoring our operational KPIs. As an early member of a start-up, this role will be frequently leaned on to tackle new challenges and opportunities as our business model evolves and to ensure that our pilots are successfully executed.


  • Implement solutions spanning people, process & technology to build a highly scalable organization with best-in-class customer experience.
  • Model our transaction economics, variable and fixed costs, and forecast out volume impacts, breakeven points, and build roadmap to profitability.
  • Define operational and product requirements to achieve customer service level goals while meeting budgeted cost levels. Prioritize product enhancement needs and advocate for resourcing to accomplish.
  • Analyze operational data to define market segments, measure health of marketplace supply and demand, and calculate price elasticity.
  • Evaluate marketplace technologies and act as project manager for implementation planning and execution.
  • Maintain a pipeline and execute a steady stream of A/B tests to better inform our decision making process and validate ideas.
  • Collaborate with CX team to model impact of policies and procedures, understand helpdesk ticket trends and incorporate input into product requirements.
  • Think through risk exposures, build a heat map for resource prioritization, build mitigation strategies, and identify & build appropriate system redundancies.
  • Develop operational health metrics and data collection methodology to execute daily, weekly and monthly reporting needs. Define data repository requirements. Provide organizational reporting and business updates to exec team and board levels.


  • Combination of 3+ years of experience in strategy or consulting roles and 3+ years of experience in operational leadership roles.
  • Demonstrated record of developing and measuring operational data to support both operational and strategic decision making.
  • Exceptional modeling abilities including operational and financial measures, sensitivity & scenario building, and adept at creation of summary exhibits and data visualizations.
  • Familiarity with lean six sigma and other continuous improvement approaches a plus.
  • Demonstrated ability and resiliency to problem solve both tactical and strategic situations; from an individual customer experience to our product roadmap.
  • Strong analytical background and capability to define a question, identify data requirements, perform data normalization and manipulation are all required. Ability to query data sources independently a plus.
  • Roll up the sleeves, willing to get dirty and do any function type of mentality.
  • Passion for bringing innovation to the insurance industry.
  • Enjoy a fast-paced environment where each day is different.
  • Exceptionally strong verbal and written communication ability.
  • Expert level spreadsheet and presentation building capability.
  • Insurance background preferred, and knowledge of claims an additional plus.


  • Opportunity to shape a very early stage company with broad involvement and influence across functions
  • Entrepreneurial environment with a diverse and collaborative culture
  • Full health benefits, including medical, vision and dental
  • Catered lunches
  • Commuter benefits
  • Gym subsidy
  • Unlimited snacks and drinks
  • Creative office space

Journey is an equal opportunity employer and encourages people from a diverse variety of backgrounds and experiences to apply. Journey does not discriminate on race, color, religion, gender, national origin, citizenship, age, disability, veteran status, marital status, sexual orientation or any other basis prohibited by law.


To apply to this position submit your resume and cover letter (optional) to: