Dear Annie - Team Lead

Dear Annie – Team Lead

Posted on March 10, 2026

Cambridge

Dear Annie , the award-winning wine bar by the people behind Rebel Rebel and Wild Child , is hiring a Team Lead . This role is a great fit for longtime servers who are ready to step into leadership without leaving the floor. If you love hospitality, enjoy supporting your teammates, and are ready for more responsibility, voice, and impact—this is a chance to build leadership skills in a collaborative, supportive environment.

Position Summary

The Team Lead at Dear Annie is a floor-forward leadership role responsible for supporting service excellence, team cohesion, and smooth daily operations. Team Leads work collaboratively with one another, our Chef, and the Director of Operations to ensure shifts are well-run, standards are upheld, and the team feels supported.

This is not a top-down management role. Team Leads share responsibility, communicate actively, and redistribute labor as needed to support the room, the bar, and one another. Success in this role depends on emotional intelligence, adaptability, and strong communication skills.

All full-time team members are offered regular paid wine education, access to industry-only tastings and events, paid company health insurance, invitations to semi-annual team outings, and generous cross-company discounts. We pride ourselves on being a collective of passionate, creative thinkers, and we support the creative endeavors of our team members within our walls whenever possible.

Core Responsibilities

Shift Leadership & Collaboration

• Co-lead shifts alongside other Team Leads with shared accountability.
• Communicate clearly and respectfully with fellow Team Leads to divide responsibilities and adapt in real time.
• Step in where coverage or support is needed, regardless of original assignment.
• Support smooth handoffs between shifts and Team Leads.

Service Standards & Guest Experience

• Lead by example on the floor and behind the bar.
• Ensure service standards are met consistently and inclusively.
• Support teammates in delivering warm, knowledgeable, and confident hospitality.
• Address service issues in the moment when possible and escalate appropriately when needed.

Team Support & Communication

• Act as a point of support for team members during shifts.
• Help onboard and support newer team members.
• Communicate shift-level feedback, wins, and challenges to fellow Team Leads and management.
• Foster a culture of mutual respect, accountability, and care.

Labor Awareness & Shared Workload

• Stay aware of staffing levels, pacing, and labor needs during service.
• Collaborate with other Team Leads to redistribute tasks and responsibilities to maintain flow.
• Support scheduling and coverage by communicating availability and flexibility.
• Recognize when additional support or intervention is needed and act early.

Operational Readiness

• Ensure the space is set up, stocked, and ready for service.
• Monitor product levels during service and communicate needs clearly.
• Help maintain organization, cleanliness, and adherence to systems.
• Support close-down procedures and ensure accurate handoffs.

Wine & Beverage Leadership

• Maintain strong knowledge of the Dear Annie wine and beverage program.
• Support guest education in an approachable, inclusive way.
• Assist team members with wine questions and service confidence.
• Uphold the values of natural wine education without intimidation or gatekeeping.

Required Skills & Qualities

• Strong communication skills and emotional intelligence.
• Proven ability to work collaboratively and share leadership.
• Comfort making decisions in real time and adapting under pressure.
• Ability to give and receive feedback with clarity and respect.
• Reliability, accountability, and follow-through.
• Enthusiasm for hospitality, food, and wine.

Preferred Experience

• Prior lead bartender, floor lead, or supervisory experience.
• Experience in high-volume or hospitality-driven environments.
• Familiarity with natural wine or a desire to deepen wine knowledge.

What Success Looks Like

• Shifts feel calm, organized, and supported.
• Team members feel seen, helped, and respected.
• Team Leads communicate fluidly and back one another up.
• Guests experience consistent, warm service regardless of who is leading.
• Problems are solved collaboratively rather than escalated unnecessarily.

Reporting & Structure

• Team Leads report to on-site management and the Director of Operations.
• Team Leads work laterally with one another and are expected to communicate openly and share responsibility.

Compensation & Schedule

• Compensation is a base hourly wage plus tips.

This is a full-time role that includes floor shifts and requires weekend and evening availability.

Employment Type(s): Full-time, Part-time

Show me how to apply

How to apply

Email: [email protected]

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