City Operations Manager
Hailo - Chicago, IL

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Join a fun, global team of top engineers, seasoned entrepreneurs, and taxi drivers for the adventure of a lifetime. We're changing personal transportation, making people’s lives easier, and opening up a multi-billion dollar market in the process.

We’ve built a massive following in London, Dublin, Toronto, Chicago and Boston, with both drivers and passengers thrilled to finally have a great experience with cabs. Join us as we expand globally.

You'll work directly with our Chicago General Manager initially to build our network and operations in Chicago, and ultimately to pursue new areas of expansion in the Midwest and beyond.

About You

You’re intelligent, analytical, disciplined, and self-aware. A day that starts with a Hailo driver training session, moves to executing a marketing event, and ends with diving into detailed operational analyses is your idea of fun. No task is beneath you, because it helps achieve a larger goal. You solve problems collaboratively and go out of your way to help team members excel. You are internally motivated, an excellent communicator, and ready to commit to an intense, independent work environment, where you’ll be required to multitask in a deadline-driven role. Past startup experience is desired.

The Role
  • Work with the City/Regional GM to continually grow and optimize the business
  • Manage, improve, and/or create our Chicago business operations/processes
  • Implement and monitor detailed operational and financial metrics, budgeting, and analyses. Work with GM locally (and others across the country) to optimize for North America
  • Identify and develop business partnerships relevant to our Chicago operations
  • Guide and manage the driver and customer relationship teams to recruit and then engage both sides of our community - from creating driver recruitment events to new marketing strategies
  • Manage our business support team to provide rapid, accurate, and informative customer service. Quickly identify systemic issues and how to solve them through smarter marketing, clearer communication and/or evolved product design
  • Over time, identify and research regional expansion opportunities, ‘break ground’ in these new locations - and then support them as they grow
  • 4+ years experience, in an operationally-focused role. Startup experience prized
  • Demonstrated creative problem-solving and collaborative execution
  • Experience working within a high-calibre, high-growth business focused on customer service and extraordinary product experiences
  • Strong understanding of business financials, operations, and analysis
  • Demonstrated entrepreneurial streak
  • Love meeting people, networking, and spreading the word about the company you love (hint: it’s Hailo!)
  • Sense of humor and perspective
  • Passion and enthusiasm to change the world
  • Degree from a top university

Very attractive salary and substantial stock options based on performance.

Why Us?

Hailo is the evolution of the hail - a free smartphone app which puts people just two taps away from a licensed taxi, and lets cabbies get more passengers when they want them.

A Hailo hail is accepted around the world every four seconds from Hailo’s global network of tens of thousands of drivers and half a million passengers. Launched in November 2011, Hailo is available in London, Dublin, Toronto, Chicago and Boston, Madrid and New York - and coming next to Tokyo, Washington DC, Cork, and Barcelona. Hailo has carried five million passengers and grown to annualized sales of over $100M.

Founded by three taxi drivers and three internet entrepreneurs, Hailo has raised over $50M from the best investors anywhere, including Union Square Ventures, Accel Partners, Wellington Partners, Atomico Ventures, Sir Richard Branson, and Janice, our CEO's mother.

The Hailo passenger app is available as a free download from the iTunes App Store and Google Play. Simply search on "Hailo". Are you a taxi driver? Visit our driver page here.


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People want to be in control of their lives so they can live the way they imagine. Hailo is a little bit of fightback against the forces of...