About Obi:

Obi is a global leader in rideshare, allowing consumers to compare prices anywhere at any time. We’re a fast-growing consumer startup, and we pride ourselves on helping consumers save time and money. Our data on rideshare pricing and consumer behavior is sought after and cited in leading publications and helps define how the industry thinks about and talks about AVs, rideshare,  and mobility.

As a culture, we are entrepreneurial, fiercely competitive, inquisitive, compassionate, creative and global in our mindset. We are a small and impactful team, with many members working together over several years. We’re growing and seeking high-impact individuals who want to work hard, have fun and make a difference. We are small team that is globally distributed

About the role:

Obi is seeking a dynamic, hard-working jack of all trades to join our team to work closely with Obi’s newly appointed CEO. You are highly conscientious and action-oriented; no task is too small or unimportant to ensure that the business is growing.

As Obi’s Chief of Staff, you will be a right hand to our CEO, working to manage her schedule, take on operational tasks to help her focus on strategic initiatives and spearhead critical projects that focus on growth. You will be a keeper of time, culture and priorities helping to ensure that the entire org is moving towards the goals we set.

Your first 90 days as Chief of Staff will focus on learning the ins and outs of our business. Expect to sit in meetings across departments and get to know the team and their biggest roadblocks and challenges. Being a great listener and note taker that can summarize insights and help shape them into next steps is critical. You’ll also do a lot of research into our new product lines, helping to shape our GTM strategy. Most importantly, over 50% of your time will be learning the ins and outs of our CEO’s schedule, how to support her and where to step in to take over operational tasks so she can focus on growth and strategy. Listening, asking questions, and taking action are critical.

Our goal is to hire someone who can work in this role for 18 to 24 months and grow into a leadership role at Obi in growth, sales / marketing or product, move on to business school or take a leadership role at another high-growth startup. We’re here to give you great experience and help you grow as a professional.

Key Priorities for this role:

Executive Administration, Finance and Operations (40%)

• Manage client relationships and ensure that billing and invoicing happen on time and accurately.
• Vendor and contractor payments and setting up systems that ensure our financial operations are running smoothly
• Work on key financial metrics for the company with the CEO, this may include creating slides for board meetings, working on the annual budget and coordinating with our external CFO and accounting teams.
• Manage CEO’s schedule as needed to help her stay on task and make sure deadlines are being met
• Organize company retreats, coordinate meetings and site visits, plan business and conference travel

Sales and Growth (30%)

• Work as the right-hand to our CEO to help win clients and close deals. This may include:
  • Building out our CRM
  • Working on sales pitches
  • Sending follow-up documentation
  • Sitting on meetings and brainstorming new ideas

Strategic Priorities: (30%)

• On a given day you may be researching the market growth for autonomous vehicles, taking notes in an investor meeting, sitting in on a brainstorm for a new advertising campaign or helping haul swag to a major event.
• The goal here is flexibility, thinking on your feet and being willing to take on any task, and knowing how to ask for help

Qualifications:

We are interviewing a wide range of candidates for this role to find the right fit in terms of personality, work ethic, organizational skills and aptitude. If you feel like you may fit some of the criteria below please do apply!

• Two to eight years in a role spanning executive administration or management, consulting, sales / marketing or operations
• Strong written and verbal communication skills
• Strong organizational and systems-thinking abilities; you’re great at tracking moving parts and connecting dots

• Experience in fast-paced, creative, or startup environments; comfort with ambiguity and shifting priorities; entrepreneurial mindset with a get-it-done attitude is a must
• Familiarity with tools like Notion, Google Workspace, Airtable, Slack, and basic content publishing workflows; ideally AI-native.

To Apply:

Required: Resume and answers to the following questions. Limit answers to 200 words each.

1. What does integrity mean to you? Can you share an example of what you mean?
2. What’s your biggest business win?
3. Please share an example of where you’ve failed. What did you learn from it?
4. What’s an improvement you would make for the Obi app?

Optional: Any examples of work (personal or professional)  that you’re proud of