Chief Technology Officer at Orchard

| Greater NYC Area
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The Company
Perch is transforming the way people buy and sell their homes. Simplifying it, to the way it should have always been; fair and true to market, straightforward, easy.
Every year in the U.S., $1.5 trillion of single family residences transact, generating over $120 billion of fees in a process that has changed little in decades. For the average American, the home purchase and sale process takes months, creates anxiety and is filled with uncertainty and hassle. 

Perch offers a modern alternative, making one of life's biggest decisions -- the sale and purchase of a home –so stress free, fair and simple that people cannot imagine any other way.

Perch applies machine learning, automation and easy-to-use interfaces to radically simplify the process of buying and selling a home. We have revolutionized the home buying process by bringing machine learning to bear with our intelligent matching engine to bring the right house to the right person and by using our ML based purchasing algorithm to determine a fair price for any house instantaneously.

Perch is headquartered in New York City, has 120+ employees and has grown 10x year over year. We have raised $250 million in financing from top tier investors including: Firstmark, Accomplice, Navitas and Juxtapose.

The Role & Responsibilities

The CTO at Perch will be a critical member of the executive team, leading our software development, dev ops, data science, information security and IT functions. The CTO will be based in our New York City office and will report to the CEO, Court Cunningham.
As the CTO, you will:

  • Lead a team of 16 developers and data scientists and be responsible for doubling the team over your first 12 months including building out the necessary technology leadership infrastructure to support the organization.
  • Inspire, motivate and foster a culture of results balanced with customer success focus that will continue to drive our 80+ NPS and high customer referral rate.
  • Own the technology processes for the company including how applications are built, supported, secured. Evolve and change the development process and tooling to keep pace with the needs of an expanding organization.
  • Be a champion for Perch throughout the marketplace. Help us drive workplace and cultural norms, both at HQ in New York and throughout all field operations, that align with Perch’s company values.
  • Be responsible for all our corporate (i.e. non-Perch developed) applications, IT, desktop support and dev ops, seeking excellence in each of these disciplines.

 Required Experience & Skills

  • 10+ years of success in technical leadership roles.
  • Proven ability to hire and retain top tier technical talent.
  • Experience with test driven development, service-oriented architecture, continuous delivery.
  • Strong systems thinker who leads though a combination personal leadership and process discipline.
  • We work with Python, Javascript/Angular, AWS, Postgres, Docker, and Kubernetes. Deep knowledge of one or more of these areas is a plus. Broad knowledge in many of them is expected.
  • Proven track record of success in goal achievement.

 Personal Characteristics
  • Results oriented with a strong work ethic. Must be driven, with the emotional intelligence to know when to push harder and when to look for alternative approaches. Solutions-focused mindset.
  • Strong customer focus
  • Track record of sound business judgment with maturity, diplomacy, and communication skills (both written and verbal). Business acumen is a critical success factor for this role. 
  • Intellectual curiosity and comfort making decisions when faced with uncertainty.
  • Strong multi-tasker with the ability to prioritize work based on business and operational needs.
  • Highly motivated, with the drive to work independently, plan and accomplish goals, manage and prioritize projects with deadlines, and ability to thrive in a fast paced, changing environment.
  • People describe you as: Passionate, a leader, a strong communicator, and someone that “gets things done.”
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Technology we use

  • Engineering
    • JavascriptLanguages
    • PythonLanguages
    • SqlLanguages
    • PandasLibraries
    • scikit-learnLibraries
    • AngularJSFrameworks
    • TensorFlowFrameworks
    • BottleFrameworks
    • PostgreSQLDatabases


31 West 27th St, New York, NY 10001
Orchard: Come With Sleeves Rolled Up, Ready To Make Real Estate Simple

An Insider's view of Orchard

How does your team reward individual success?

We recognize employees in a variety of ways on a regular basis. At Orchard feedback is a gift and every employee truly lives out our company values. Our team makes a point to shout out individual successes in our #shoutouts channel in Slack and every month during Town Hall. Not an ounce of hard work goes unnoticed!


Executive Assistant

What kinds of technical challenges do you and your team face?

Each home is unique and comes with its own challenges and surprises. Even though our team has been through hundreds of transactions, we're always learning, growing, and improving our process with each home we acquire. On the engineering side, that means never being satisfied and constantly pushing ourselves to iterate quickly and deliver quality.



What makes someone successful on your team?

Curiosity, scrappiness, and a sense of urgency. We move quickly to accomplish our goals, but leave time and space to think outside the box. All of our functional areas work together to build an exceptional brand, product, and customer experience, so communication and collaboration are key skills as well.



What is your vision for the company?

We're looking to make buying and selling a home as easy as trading in a car. We believe that through technology, human-centered design, and exceptional operations we can remove the friction from the biggest financial transaction of our customers' lives. As a team, we get to make real progress towards achieving this vision every day.


Growth & CX

How do your team's ideas influence the company's direction?

At Orchard, our mission is to provide the most stress-free, fair and simple way to buy a home. The Investments team that I lead contributes to this mission by providing a fair market value estimation for our customers’ homes. Our approach integrates human judgement alongside an internal valuation algorithm to price every home.


Investments Manager

What are Orchard Perks + Benefits

Eat lunch together
Intracompany committees
Daily stand up
Open door policy
Team owned deliverables
Team based strategic planning
Group brainstorming sessions
Open office floor plan
Dedicated Diversity/Inclusion Staff
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Dental Benefits
Vision Benefits
Health Insurance Benefits
Retirement & Stock Options Benefits
Company Equity
Child Care & Parental Leave Benefits
Generous Parental Leave
Vacation & Time Off Benefits
Unlimited Vacation Policy
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
Stocked Kitchen
Some Meals Provided
Happy Hours
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