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Careers at Good Trouble Bourbon

Fractional Head of Ecommerce & Revenue

company
Good Trouble Bourbon
location
Chicago, IL, United States (remote)
work mode
remote
posted
30 Sept
  • **Good Trouble | Reports to CEO Dee M. Robinson
  • Engagement: Fractional contract; ongoing engagement with an initial 90-day execution plan. Potential full-time opportunity.
  • Location: Remote, with availability for team collaboration
  • About Good Trouble
  • Good Trouble is a premium bourbon and lifestyle brand built around Conversation, Connection, and Change. Through award-winning bourbon, meaningful storytelling, jewelry, merchandise, and experiences, we bring people together and invite them to Pour It Forward.™ We believe Great conversations build what’s next. ™
  • We are seeking a hands-on commercial leader to turn brand interest into purchases, build lasting customer relationships, and grow ecommerce revenue across our product portfolio.
  • The Opportunity
  • The Fractional Head of Ecommerce & Revenue will own the strategy and execution of Good Trouble’s digital sales engine - from customer acquisition and storytelling to conversion, retention, and reporting.
  • This person will work directly with the founder and lead the work of creative, technology, marketing, and fulfillment partners. Success requires both commercial judgment and the willingness to build campaigns, improve customer journeys, manage details, and deliver results.
  • The immediate priority is a coordinated holiday sales program, followed by a repeatable approach to year-round growth.
  • Key Responsibilities
  • Own ecommerce performance and revenue planning
  • \* Establish revenue goals, channel budgets, forecasts, and a clear weekly execution plan.
  • \* Grow sales across bourbon purchasing pathways, jewelry, merchandise, gifting, and limited releases.
  • \* Track revenue alongside contribution margin, acquisition costs, and customer retention.
  • \* Identify and resolve barriers to purchase, including weak product pages, unclear offers, checkout friction, and fulfillment issues.
  • Lead storytelling that drives sales
  • \* Translate the founder’s voice, brand mission, product quality, and cultural relevance into compelling campaigns.
  • \* Own the commercial campaign calendar, including holiday gifting, product launches, events, and seasonal promotions.
  • \* Brief and direct creative partners on the assets needed for email, social, landing pages, advertising, and product pages.
  • \* Ensure every campaign has a defined audience, offer, call to action, purchase path, and measurement plan.
  • Build and operate CRM and lifecycle marketing
  • \* Organize customer data and establish useful audience segments.
  • \* Implement and optimize welcome, abandoned-cart where supported, post-purchase, repeat-purchase, gifting, and reactivation campaigns.
  • \* Lead email and, where appropriate, SMS marketing, including consent practices and list quality.
  • \* Convert event attendance, QR engagement, founder visibility, and social interest into measurable customer relationships and purchases.
  • \* Coordinate any community or membership platform launch with the customer journey and revenue plan.
  • Improve acquisition, conversion, and retention
  • \* Manage paid media partners and evaluate spending against agreed performance targets.
  • \* Develop and test offers, bundles, gifting experiences, referral opportunities, and product recommendations.
  • \* Improve the ecommerce experience through practical testing and customer feedback.
  • \* Build a coordinated path from discovery to purchase and repeat engagement.
  • Lead partners and commercial operations
  • \* Set priorities, deadlines, and accountability for agencies, freelancers, developers, and fulfillment partners.
  • \* Coordinate inventory availability, launch readiness, customer service, shipping communications, and delivery expectations.
  • \* Work with authorized alcohol commerce and fulfillment partners to ensure campaigns accurately reflect purchasing eligibility and availability.
  • \* Identify capabilities the business needs and recommend resources within an agreed budget.
  • Provide clear reporting and decisions
  • \* Maintain a concise dashboard covering sales, conversion, average order value, acquisition costs, repeat purchases, campaign performance, and contribution margin.
  • \* Lead a weekly review of results, obstacles, priorities, and decisions required.
  • \* Distinguish measurable sales impact from engagement metrics and document what should be expanded, improved, or stopped.
  • First 90 Days
  • First 30 days
  • \* Assess the storefront, bourbon purchase pathways, customer data, marketing systems, vendor responsibilities, and fulfillment readiness.
  • \* Establish baseline performance, tracking, and revenue targets.
  • \* Deliver a prioritized action plan and launch calendar.
  • \* Address the most urgent conversion issues and activate essential CRM campaigns.
  • Days 31–60
  • \* Execute coordinated sales campaigns across products and channels.
  • \* Launch audience segmentation and targeted lifecycle marketing.
  • \* Improve priority product pages, landing pages, gifting offers, and event capture journeys.
  • \* Establish a reliable operating rhythm with all partners.
  • Days 61–90
  • \* Demonstrate measurable progress against agreed revenue and profitability targets.
  • \* Optimize campaigns using actual purchasing behavior.
  • \* Present a forward revenue forecast, budget recommendation, and growth plan.
  • \* Document repeatable processes and clarify ongoing staffing needs.
  • Ideal Qualifications
  • \* Demonstrated leadership in ecommerce growth for premium consumer, lifestyle, gifting, or beverage brands.
  • \* Strong experience with Shopify or comparable ecommerce platforms, CRM, email marketing, analytics, and conversion optimization.
  • \* Proven ability to connect brand storytelling with commercial results.
  • \* Experience managing agencies and executing campaigns within a lean team.
  • \* Financial fluency in revenue forecasting, customer acquisition costs, margins, and retention.
  • \* Ability to work effectively with a founder while independently driving priorities and execution.
  • \* Alcohol ecommerce experience is highly desirable, including familiarity with third-party purchasing and fulfillment arrangements.
  • \* Experience with community or membership platforms is helpful.
  • What Success Looks Like
  • Success means sustained growth in profitable ecommerce revenue, stronger conversion and repeat purchasing, a functioning CRM program, and campaigns delivered accurately and on time. Performance targets will be established after the initial assessment and agreed with the founder.
  • Engagement Structure
  • We anticipate approximately 15–20 hours per week initially, with capacity adjusted around launches and peak selling periods. Candidates should propose a monthly retainer, availability, and the resources required to deliver the scope. Any performance incentive will be tied to agreed, measurable commercial outcomes.
  • To Apply
  • Please submit:
  • \* A resume or relevant professional profile.
  • \* Two or three examples of ecommerce growth you directly led, including your role, starting conditions, timeframe, and measurable results.
  • \* Your proposed approach to the first 90 days.
  • \* Your availability, monthly fee, and any additional execution resources required.
  • \* Two relevant client or employer references.**
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