Chief of Staff to the Office of the CTO

Chicago, IL
Jul 21, 2022
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At, we are building products that empower millions of home buyers, renters, dreamers, and real estate professionals. We aim to radically simplify the home buying/selling process, and to help more people achieve the dream of home ownership. To help us achieve this mission we are looking for a Chief of Staff to office of the CTO.

As a part of our team, you’ll engage with an amazing and inclusive group of teammates and leaders, learn and innovate, have a huge impact, and have a great time doing it. If you enjoy working in a fast-paced, dynamic work environment and have a desire to grow yourself while making a meaningful impact on our business and users, then make the move!

As a member of the Tech Strategy and Delivery team, you will work directly with the CTO and CTO Staff to lead critical engineering programs, drive strategic alignment and communication across the 600+ person technology organization, and support our long term engineering strategy. You’ll also be a thought partner and central point of coordination to help Tech grow, scale and run more effectively. In this role, you will manage the key operational routines, oversee critical business priorities, and lead special projects on behalf of the CTO. You will partner closely with CTO Staff and key stakeholders across functions and deliver time sensitive requests. This role reports directly to the VP, Tech Strategy and Delivery.

The ideal candidate will be an experienced business professional and possess exceptional communication and relationship management skills. This person will be able to think creatively and work independently to proactively solve problems. A successful candidate will be able to prioritize tasks in a fast-paced environment and communicate effectively to audiences of varying levels of seniority. We're looking for someone who thrives when working in a fast paced environment and enjoys tackling ambiguous problems.

What You Will Do

  • Support CTO and CTO Staff on high priority and at times confidential initiatives and deliverables related to Tech’s strategy, growth, structure, and operating rhythms - including preparing materials, briefing documents, speaker notes, meeting and offsite agendas, etc.
  • Prepare materials and decks for CTO/CTO Staff and manage cadence of weekly, monthly and quarterly routines, ensuring clear objectives are set and follow-through on decisions/action items achieved e.g. Tech Tuesday, CTO Staff meetings, All Hands, Tech Leadership Connect, AMAs, #realtalks etc.
  • Develop compelling, data-driven communications on behalf of the CTO
  • Synthesize critical information and frame key decisions for senior leaders in partnership with core teams
  • Track and proactively manage action items and next steps to ensure key milestones are met and items resolved in a timely manner
  • Launch and lead key initiatives for the CTO and CTO Staff

Who You Are

  • Expert stakeholder management, influencing and storytelling/communication skills, both verbal and written - able to convey complex information in a concise manner to facilitate decision making
  • Extremely strong written, slide preparation and spoken skills to present ideas and actions with clarity
  • Proven track record of project managing complex cross-functional projects while maintaining an efficient plan, tracking issues, and proactively communicating progress against project milestones; high attention to detail
  • Proven ability to lead and execute quickly and independently in a highly visible and fast-paced environment
  • Adept at building trust-based relationships with stakeholders; able to collaborate effectively across a wide range of teams and seniority in the organization
  • A ‘hands on’ attitude - comfortable diving into execution and operational matters, while maintaining focused on the longer term strategic agenda
  • Advanced MS Office or Google Suite skills
  • Bachelor's degree required, Masters of Business Administration preferred
  • 10+ years of experience, ideally in corporate strategy, management consulting and/or a similar role in a leading technology company; real estate experience a plus

Do the best work of your life at

Building your career? Build it better at®. Here, you’ll partner with a diverse team of experts as you use leading-edge tech to help people meet a crucial goal: finding their way home. And you’ll find your way home too. People are our foundation—the core that drives us passionately forward. At, you’ll bring your full self to work as you innovate with speed, serve our consumers, and champion your teammates. In return we’ll provide you with a warm, welcoming, and inclusive culture; intellectual challenges; and the development opportunities you need to grow.

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