Head of Broker Operations

| Greater NYC Area
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The Company

Orchard 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.

Orchard offers a modern alternative, making one of life's biggest decisions – the sale and purchase of a home – stress free, fair and simple.

Orchard launched in 2017 and was previously known as Perch. The company is headquartered in New York City, has 150+ employees and has grown 10x year over year. We have raised over $300 million in financing from top tier investors including: Firstmark, Accomplice, Navitas and Juxtapose.

Role and Responsibilities

The Head of Broker Operations at Orchard will be a critical member of the leadership team, driving a superior customer experience for all Orchard customers. The Head of Broker Operations will be based in either our New York City or Austin, TX offices and will report to the CEO, Court Cunningham.

Broker Operations at Orchard is responsible for: 

  • Ensuring our customers can close on their new and old home on-time and without issue
  • Enabling customers to sell their home on-market for the highest possible price, as quickly as possible
  • Doing all of the above with industry-leading SLAs and in 100% compliance with all state and federal laws

The operations team consists of both consumer-facing title officers, closing coordinators, and listing agents as well as an internally focused contract operations team. Many of our customers cite their experience with their title officers and closing coordinators as a top reason they’d refer us to a friend. Continuing to build our brand as the leading customer-centric service will be critical to the company’s future success.

As the Head of Broker Operations, you will:

  • Hire 35+ service team members growing the team from 30 to 65 across our Dallas, Austin and New York City offices.
  • Build & refine scalable processes and systems to enable the Orchard team to deliver consistently against goals.
  • Collaborate with Sales and Product Management using data to diagnose problems, develop actions plans, and drive operational excellence.
  • Collaborate cross-functionally to understand and continuously improve all parts of Orchard’s business operations
  • Be a champion for Orchard throughout the marketplace. Help us drive workplace and cultural norms, both a HQ in New York and throughout all field operations, that align with Orchard’s company values.

The KPIs this role will be particularly focused on are on-time customer closings, customer satisfaction, timeline SLAs, and operational efficiency.


  • 10+ years of success in operations leadership roles with experience managing across multiple geographies.
  • Proven ability to hire and train teams of 75+ people
  • Strong systems thinker who leads teams though a combination personal leadership and process discipline.
  • Proven track record of success in goal achievement.
  • Some domestic travel required in first year (assume ~25%)
  • Experience working with product to design software to improve and optimize the performance of operations.
  • Bachelor’s Degree.

Who You Are

  • Highly effective at building collaborative relationships across our entire organization. 
  • Leadership skills to motivate team members of all levels and backgrounds.
  • An entrepreneur who sees ambiguity as opportunity, and obstacles as chances to build new solutions.
  • Superior analytical skills, attention to detail with a data-driven mentality, and high intellectual curiosity. Propensity to question the status quo and search for ways to make it better.
  • Track record of good business judgment with maturity, diplomacy, and communication skills (both written and verbal). 
  • Results orientation with a strong work ethic. Must be tenacious, with the emotional intelligence to know when to push harder and when to look for alternative approaches. Solutions-focused mindset.
  • High energy and action-oriented with a history of getting things done in complex, fast moving environments. Successful in scrappy and entrepreneurial environments, with a drive to get things done. 
  • Strong multi-tasker with the ability to prioritize work based on business and operational needs.
  • 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

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

What are some social events your company does?

Our culture committee really enjoys planning the monthly happy hours in the office. We have different cocktails, beer and yummy foods from some of our favorite restaurants! It's a great way for everyone to sit back and catch up with each other. As our team grows, we’re looking forward to planning more outings, like our upcoming bowling competition!


People Ops

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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