Two Chicks With A Side Hustle

Have you ever wanted to disrupt a $70bn industry and be a key member of a fully integrated consumer and business-facing marketing company which is 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 member engagement while maintaining the nimbleness of a data-driven, digital company? Are you keen to help a young, fast-growing company continue to evolve into a world-class, employer of choice? Well, then, come say hi!

Firstleaf is looking for a Wine Concierge/Retention Specialist to join our team. In this multifaceted role, you will drive engagement with new and repeat customers to ensure a seamless customer experience.

A few examples will illustrate some of your goals:

  • You’ll build relationships with members and have the ability to discern member preferences to provide recommendations to help cultivate the perfect wine order
  • Generate revenue by upselling, whether it be to a different membership tier or adding additional bottles to an order
  • Proactively contacting members via outbound calls and emails for retention campaigns and to ensure members are enjoying our club
  • Use product knowledge to showcase solutions for customer service matters and assist the call center as needed
  • Data entry of customer engagements via database/CRM/other software to track progress


  • Compensation: $22- $24 per hour depending on experience
  • Schedule: Sunday – Thursday, 8:30 AM-5:00 PM Pacific Time
  • Stable internet requirement of 100 Mbps download speeds and 50 Mbps upload speeds with 99% uptime with no bandwidth or data caps. Wired ethernet from modem to laptop without adaptors. Wi-Fi, fixed wireless, cellular or other hotspots are not supported.
  • Must have a suitable home environment free from distractions and background noise


  • Superior time management skills
  • Previous outbound calling (these are not cold calls) and contact center experience
  • Excellent rapport-building and listening skills
  • Ability to empathize with customers and provide solutions
  • Excellent communication skills both written and verbal
  • Ability to type at least 40 WPM
  • ZenDesk and prior wine experience are a plus
  • Eligibility to work in the U.S.


Compensation: $22- $24 per hour depending on experience

Working with the world’s best wine company isn’t enough? Seriously though, we offer remote work. Two weeks of paid vacation time and nine floating holidays. We offer a competitive compensation package and stock options grants, plus choices with medical, dental and vision coverage, as well as flexible spending accounts, life insurance, 401(k), employee assistance program, and discounted pet insurance. And to top it off: a monthly wine credit with our wine club and employee wine tastings!

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