Who are we?

Sidewalk Labs is an Alphabet company with a mission to radically improve urban life. We aim to create inclusive, large-scale communities by bringing together an innovative planning approach, products and services designed to address urban challenges, and capital for real estate and advanced infrastructure. 

Since our founding in 2015, we've grown into an organization of over 100 employees based primarily in New York and Toronto. Our cross-disciplinary team consists of experts from real estate, urban planning, government, finance, technology, and engineering, among other backgrounds.

To date, we've incubated and invested in multiple companies focused on solving city problems, and we've launched the Sidewalk Toronto project, which aims to create a community along Toronto's waterfront that achieves new standards of sustainability, affordability, and economic opportunity for all.

With the potential to catalyze and scale new models for inclusive growth, our work is both highly exciting and complex. We are working to achieve something unprecedented — help us build it!

What is the role?

As Chief of Staff, you will provide leverage for Josh Sirefman, our President who oversees Sidewalk’s work in Toronto, Sidewalk Urban Development (SUD), Sidewalk Urban Systems (SUS), and the Policy and Communications team. In this role you will report directly to the President and interact with business unit leaders, company leadership, and all levels of staff. 

You will need to be highly strategic and tactical in your work, as a key part of this role will require you to manage the operations for a sizable part of our organization.  This means you will drive important internal processes, manage decision-making channels, prioritize deliverables for the SUS, SUD, and P&C teams, and measure progress against both goals and timelines. Success will require strong management skills, deep experience navigating complex and ambiguous organizations effectively, superior people skills, and high emotional intelligence as you navigate workstreams and timelines with the businesses and with Sidewalk’s Corporate Services team. 

We see the Chief of Staff role as an excellent opportunity for someone with a strong operational skill set and interest in our work to become deeply embedded in our fast-paced, complex business. 

In this role you'll be responsible to:

  • Track decision making processes related to budget, allocation of resources, prioritization according to SWL processes.
  • Ensure effective operation of our Partnership Development Committee, as well as other operational decision-making venues or processes.
  • Support business unit (SUD & SUS) leads in maintaining master timelines and schedules, incorporating project milestones and other relevant inputs to ensure application of deadlines.
  • Work with business leads (SUD, SUS, Policy and Comms and SWTO) to manage the development and application of Objectives and Key Results (OKR), or other metrics and milestones, as appropriate, and manage consolidated OKR’s across business units.
  • Serve as primary liaison and conduit with Corporate Services for the business units.
  • Ensure internal communications across business units, and across other Sidewalk business units and Corporate Services; design and maintain systems for communications and information sharing.
  • Support President as needed, including coordination of materials and preparation for internal and external meetings and events; coordination with CEO and COO; strategic management of President’s schedule and priorities; and represent President as needed in meetings.


After 3 months, you are...

  • A Proven Operator. You’ve developed an understanding and are deeply engaged in all SUD, SUS, and P&C operational processes. You’ve gotten your feet wet leading the planning and tracking of business unit OKRs, budget, and initiatives.
  • Leverage for the President. You already own and facilitate key meetings on behalf of the President. You’re filling in the gaps and diving into key team initiatives as needed in his stead. 
  • Driving the Business Forward. You thoroughly understand our roadmap and objective and hold us accountable to them. You know everything that is going on—or not going on - the President is never surprised. 
  • A Trusted Partner. You have begun to build trust with the President and can broker difficult relationships and resolve disputes to protect the President’s time and keep him focused on important matters. Further, you can act as the proxy by standing in for, negotiating, and/or making decisions on behalf of the President (when appropriate).

After 12 months, you are...

  • The President’s go-to Advisor. You offer guidance across a host of business and employee issues; the President respects and welcomes your intuition and has full trust in your ability to drive priority issues.
  • Fluent in the business. You have gained the trust and respect of the organization, including all senior executives. You know what needs to get done, how it needs to get done, and when it needs to get done. 
  • You’re a true proxy for the President. You are a surrogate without question in internal and, when appropriate, external settings. 

What leads to success

You have a graduate degree and several years (8-15+) of work experience with a background in real estate development or management consulting. Ideal candidates will have experience in both. To succeed in the role, you must be exceptional at managing complex projects and processes in a commercial and client-facing environment. You should enjoy running management and organizational processes (team meeting agendas, performance cycles, etc) and constantly improving tools and systems. You should have touched cities in some capacity during your work experience, because this will help you get up to speed quickly in our quick-moving, ever-evolving work environment.

We are very excited to hear from you.

The community of the future is a place for everyone, and Sidewalk Labs is proud to be an equal opportunity employer. We encourage individuals from underrepresented groups to apply. All employment is based on merit and business needs. 

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