Entertainment Manager
Location: Sessions by the Bay, National City, CA
Job Type: Full-time
Classification: Salaried, exempt
Compensation: $75,000 annually
Department: Entertainment, Events & Partnerships
Reports To: CEO
Overview
Sessions by the Bay is looking for an Entertainment Manager to lead our event calendar, entertainment relationships, cultural partnerships, and live programming strategy.
This is an opportunity to help shape one of Southern California’s most unique hospitality and entertainment destinations. Sessions combines a legal cannabis consumption lounge, dispensary, dining, immersive experiences, music, art, wellness, nightlife, and community programming under one roof.
We are looking for someone who understands what makes people want to go out, gather, and return. The right person can identify great entertainment, develop new event concepts, build relationships, create energy around the venue, and turn ideas into well-organized experiences that drive attendance and support the business.
This is not simply a talent-booking position. It is a full-time ownership role for someone who can manage the calendar, coordinate partners, use company systems, work across departments, support event execution, and evaluate what is producing results.
The person in this role will also serve as a visible Sessions brand ambassador and should be comfortable hosting events, working a room, introducing performers, engaging guests, and speaking on a microphone.
What You’ll Do
- Own and develop the Sessions weekly, monthly, and seasonal entertainment calendar.
- Book and manage relationships with DJs, bands, comedians, performers, hosts, promoters, instructors, artists, and event producers.
- Create new recurring events, themed experiences, cultural programming, educational events, private events, and brand-supported activations.
- Maintain programming at least 60 to 90 days in advance whenever possible.
- Evaluate talent based on quality, professionalism, audience fit, promotional effort, cost, and ability to contribute to the guest experience.
- Establish clear expectations with entertainers and promoters regarding promotion, social media participation, guest lists, ticketing, arrival times, and event responsibilities.
- Develop creative payment structures that may include guarantees, ticket incentives, attendance bonuses, or revenue participation.
- Build relationships with influencers, artists, athletes, media personalities, community figures, and cultural tastemakers.
- Identify opportunities for hosted visits, content collaborations, appearances, and partnerships that introduce Sessions to new audiences.
- Work with the Buyer to coordinate cannabis brand sponsorships, product launches, and event activations.
- Work with the Brand Manager and marketing team to make sure events are promoted clearly, consistently, and early enough to build momentum.
- Use the company CRM and internal systems to track contacts, bookings, commitments, event details, follow-ups, and performance.
- Create organized event plans and coordinate with operations, lounge leadership, retail, kitchen, security, and marketing.
- Host and facilitate key events, including introductions, announcements, sponsor moments, giveaways, and audience participation.
- Track attendance, reservations, ticket sales, event costs, sales performance, promotional participation, and overall event results.
- Recommend which events and partners should be repeated, improved, expanded, or replaced.
What We’re Looking For
- Three or more years of relevant experience in entertainment booking, event management, nightlife, hospitality, festivals, promotions, talent management, venue programming, radio, or event production.
- Strong knowledge of music, culture, entertainment, hospitality, and live event environments.
- Existing relationships within the San Diego entertainment, music, nightlife, cultural, or influencer community are strongly preferred.
- Experience managing a calendar or portfolio of events from concept through execution.
- Strong organizational, communication, negotiation, and project management skills.
- Willingness to consistently use CRM, calendar, project management, spreadsheet, and reporting systems.
- Ability to balance creativity with business judgment, budget awareness, and operational realities.
- Comfortable speaking on a microphone, hosting events, working a crowd, and representing a brand publicly.
- Strong presence, personality, cultural awareness, and ability to connect with different types of people.
- Ability to manage multiple events, relationships, and deadlines at the same time.
- Experience working with multicultural, bilingual, or cross-border audiences is a plus.
- Cannabis industry experience is helpful but not required.
- Must be at least 21 years old.
Ideal Candidate
The ideal candidate is creative, connected, organized, commercially aware, and naturally engaging.
They understand that a great event requires more than a good idea or a talented performer. It requires planning, promotion, accountability, communication, execution, and follow-through.
They are comfortable both behind the scenes and in front of the room. They can develop the calendar, negotiate with talent, manage details, work inside company systems, and step onto the microphone when the event needs energy.
A strong network and personality are valuable, but they are not substitutes for organization, availability, judgment, and ownership.
Schedule and Availability
This is a full-time position with a flexible schedule based on the entertainment calendar.
The role requires regular on-site presence and availability for key evenings, weekends, holidays, and special events. The person will not need to attend every event, but they will be expected to lead major programming and remain closely connected to execution.
Candidates with significant outside entertainment, touring, freelance, or weekend commitments must be able to demonstrate that those commitments will not interfere with their responsibilities to Sessions.
This position should be treated as the employee’s primary professional commitment.
About Sessions by the Bay
Sessions by the Bay is San Diego County’s first legal cannabis consumption lounge, dispensary, dining venue, immersive experience, and live entertainment destination.
Our programming includes live music, DJs, comedy, drag brunches, wellness activities, art experiences, movie nights, educational events, cannabis brand activations, cultural programming, and recurring community events.
We are not simply looking to fill dates on a calendar.
We are looking for someone who can help make Sessions the place people want to be.
Pay: $75,000.00 per year
Benefits:
- 401(k)
- Dental insurance
- Employee discount
- Health insurance
- Vision insurance
Application Question(s):
- Describe an event, recurring program, or entertainment calendar you personally helped develop and manage. What was your role, and what results did it produce?
- How have you worked with entertainers, promoters, influencers, or event partners to help promote an event and drive attendance? Please provide a specific example.
- What systems or tools have you used to manage contacts, bookings, calendars, event details, deadlines, and follow-up?
- This role requires regular evening and weekend availability and should be treated as your primary professional commitment. Do you have any ongoing work, touring, freelance, or personal commitments that could interfere with that availability? Please explain.
- Optional: Please provide a link to a professional website, LinkedIn profile, portfolio, or public social media account that helps us better understand your experience, work, or professional presence.
Work Location: In person
