Head of Finance & Strategy at Orchard

| 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.

We are proud to be recognized by Inc. Magazine as a best workplace of 2020 and have a 4.9 Glassdoor rating!

Role and Responsibilities

The Head of Finance & Strategy will be a critical member of the Orchard team, located in New York, NY. This position will report to Sean Roberts, Chief Financial Officer / Head of Finance and Real Estate, and it will have broad responsibility across the Company’s strategic finance areas, including: business intelligence / reporting, financial planning and analysis, and capital markets / investor relations (both equity and debt).

As the Head of Finance & Strategy, you will:

  • Collaborate with Orchard's CFO and broader executive team, other finance functions, underwriting/investments team, and operational teams across the company.
  • Thought partner with executive team to lead business case and scenario analysis to drive intelligent decisions which inform company strategy.
  • Lead team that develops and maintains financial forecasts for the business and tracks key variances, changes and opportunities in actual results vs forecasts.
  • Lead team that generates, maintains and automates financial and operational reporting, including weekly, monthly and quarterly packages for key internal and external stakeholders.
  • Partner with the CFO/ Head of Real Estate (and many other stakeholders) to ensure all operating and financial metrics are properly defined, monitored, and being met. You (and your team) will monitor both asset-level and market-level KPIs/metrics on a daily, weekly and monthly basis and help operating teams develop initiatives to optimize them
  • Be responsible for maintaining the company’s financial model and unit economics for presentation to internal stakeholders, the Board and investors.
  • Oversee annual budgeting process and long-term strategic planning from a financial perspective.
  • Partner with our internal Accounting team on monthly close process, financial reporting, and preparation of GAAP financial statements; work with the CFO and Controller to define and implement best practices for financial management and reporting across the Company.
  • Be actively involved with capital markets activities, including equity fundraising and debt financing; closely involved with the CFO and CEO.
  • Be a champion for Orchard!

Required Experience

  • Bachelor’s Degree in Finance, Economics, or a related field. MBA preferred, but not required
  • At least 7+ years professional experience. 5+ years within FP&A function or private equity/growth equity/ venture capital investment background preferred.
  • Strong understanding of corporate finance concepts and accounting principles.
  • Proven ability to build & manage high performing finance teams.
  • Experience developing highly complex financial models and developing reporting packages, preferably at a high-growth company. 
  • History of successfully leading business case analysis and planning processes which set strategy through a financial lens, then tracking the plan to report on its progress over time.
  • Experience participating in debt & equity financing processes.
  • Proven track record of success in exceptional goal achievement.
  • Experience working in a technology-driven environment. 
  • Exceptionally advanced Excel and financial modeling skills; strong PowerPoint skills.
  • Proficiency with a business intelligence tool (ideally Looker) and basic SQL proficiency are desired.

 Personal Characteristics

  • You think like an investor: Capable of high-level strategic thinking (seeing the “bigger picture”) while simultaneously being able to dive into granular details -- all through a quantitative, financial lens 
  • You execute like an entrepreneur: 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
  • Exceptionally strong analytical skills with relentless attention to detail backed by a data-driven mentality. Genuine intellectual curiosity 
  • Track record of good business judgment with maturity, diplomacy, and strong leadership and communication skills (both written and verbal). Can run processes and meetings independently 
  • Highly effective at building collaborative relationships across our entire organization. 
  • An entrepreneur who sees ambiguity as opportunity, and obstacles as opportunities to build new solutions
  • Demonstrated ability to roll-up sleeves and work with team members (at all levels of the Company) in a hands-on management capacity
  • 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
  • A strong multi-tasker with the ability to prioritize work based on business and operational needs. Ability to manage time effectively
  • Ability to work under high pressure and to meet deadlines 
  • 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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