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Director of Strategic Initiatives

Penrose Hill

1 month ago

Job type: Full-time

Remote (USA Only)

Hiring from: USA Only

Category: Business

Have you ever wanted to lead special projects at a fully integrated consumer and business facing marketing company supported by a supply chain that stretches from the US to Europe and across the Southern Hemisphere? Do you fancy a deep-dive into the intricate details of innovation in the production and manufacturing of physical goods (specifically wine) while maintaining the nimbleness of a data-driven, digital company? Are you keen to help a young, fast-growing company continue to evolve into the world's most customer-centric wine company? Well, then, come say hi!

Firstleaf/Penrose Hill is looking for a versatile Director of Strategic Initiatives to report directly to the CEO and solve critical problems. In this multi-faceted role you will assist with the research, development and implementation of new Penrose Hill (PRH) initiatives, programs, projects, and activities designed to grow, enhance and maintain the organization’s reputation and revenue.


Some of the projects you might tackle:

  • New product development: stand in for CEO in certain internal meetings, helping the company identify product or feature improvements based on customer and department feedback. For example, in a weekly Customer Experience meeting, you may notice that a lot of customers are displaying an unusual and interesting behavior. Is this an anomaly, or does it point to a larger problem and if so, help the CEO and the company to recognize, address and correct.
  • Financial modeling: help build and improve the company financial models, as well as standalone scenario analyses (such as: how much would acquisition cost need to change for free shipping to pay for itself? how should we price third party products on the site to be competitive in the industry, yet to be accretive to overall gross profit dollars?)
  • New lines of business: explore and evaluate new potential business lines, ranging from other categories, accessories or geographical markets. eg. should we sell stemware and other accessories? Do we partner via an affiliate model?

We're a rapidly growing company- and if you're passionate, hardworking, and capable, if you crunching the numbers and solving seemingly impossible issues appeals, this may be the best job you'll ever have.



  • MBA and/or degree holder in Business Administration or Economics; would be an added advantage with Accounting or Actuarial background;
  • Exceptional project management experience
  • Track record of thinking conceptually and mastering complex subject matter quickly
  • Highly numerate with a sound understanding or what lays behind numbers and drive revenues and profitability
  • Advanced Excel skills including macros, pivot tables and data modeling
  • Ability to work independently and proactively to work on the projects, as needed
  • Strong presentation skills, ability to exercise initiative, and be a self-starter;
  • Relationship builder with strong organizational skills and demonstrated capacity to develop and implement practical strategies, plans, and solutions to identified issues and problems;
  • Excellent problem-solving, analytical skills and impeccable business judgment
  • Excellent writing skills to write concisely and in an organized manner
  • Proficient in MS Word, Excel and PowerPoint.



Working with the world's best wine company isn't enough?

Seriously though, we offer remote work, and a location agnostic philosophy added to a very flexible work schedule. Unlimited vacation time. Further, we offer a truly competitive compensation package with bonus and stock options grants, plus choices with medical, dental and vision.coverage. Flexible Spending Accounts. Life insurance, 401(k), Employee Assistance Program, Discounted pet insurance. And to top it off: a wine credit and discount with Firstleaf.


Before you apply, please check if any restrictions apply in terms of time zone or country.

This job has a geo-restriction in place: USA Only.

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