Enrollment Director, Sales

Little Gay Book is a high-end professional matchmaking service dedicated to supporting and uplifting the LGBTQ+ community. We offer personalized matchmaking, speed dating events, coaching, and community-focused gatherings that foster meaningful connections. We create inclusive, welcoming spaces where people can meet, learn, and grow in their relationships and social lives.

Our sister company, Little Black Book , is a bespoke, high-touch matchmaking service for discerning heterosexual professionals.

Our team works in a mission-driven environment that values authenticity, respect, and community-building.

We are looking for an experienced Enrollment Director/Sales to lead membership enrollment for both Little Gay Book and Little Black Book. You will engage prospective clients, explain our matchmaking services, and guide people through enrollment with professionalism and care. You will turn new and existing leads into members, build lasting client relationships, and work closely with our matchmaking and events teams so every client has a great experience.

This role drives revenue while representing our values of inclusion, integrity, and care.

This is a remote, independent contractor position paid on a 1099 basis.

• Monthly sales quotas are set for this position.
• Tiered Commission Structure: Reaching monthly sales targets unlocks higher commission rates, allowing you to earn increased payouts as you surpass your goals.
• Uncapped earning potential based on sales performance.

Membership Enrollment

• Convert new and existing leads into members
• Update the team on the status of leads and clients

Sales Process

• Call and message new and existing leads to book consultations on your calendar
• Conduct consultations via Zoom
• Present service packages and close sales in a consultative, affirming way
• Follow up as needed to close
• Review and refine the sales process and strategy

Client Relationships

• Maintain ongoing relationships with clients and provide customer support
• Work with the matchmaking and events teams to deliver a seamless client experience

Brand Representation & Media

• Represent Little Gay Book and Little Black Book positively and professionally in public-facing opportunities
• Participate in social media content, including posts, videos, interviews, and other promotional content as appropriate
• Participate in podcast, television, digital media, or other interview opportunities when available
• Collaborate with the team to promote the companies, services, events, and membership opportunities
• Be comfortable speaking about matchmaking, dating, relationships, and the company's mission in an engaging and authentic way

Administrative

• Document every sales step in the database and the leads tracker
• Write detailed client discovery notes in the database to support the service team
• Complete weekly and monthly reports
• Track and manage payments on sales as needed
• Follow all lead nurturing steps
• Assist team members during the sales process for their prospective recruits

Meetings & Training

• Weekly Sales Meeting: set strategy to hit sales goals
• All Team Meetings and Matchmaker Meetings

• Meet or exceed monthly sales quotas
• High conversion rate of new leads
• Actively nurture existing database leads
• Maintain accurate and timely sales and client records
• Represent the brands professionally and consistently in client-facing and public-facing opportunities

Required

• Experience in the matchmaking industry
• Proven sales skills, including prospecting, presenting offerings, and closing deals in a consultative manner
• Strong communication skills, including active listening and the ability to explain things clearly and respectfully
• Proven customer service experience focused on empathy, problem-solving, and client satisfaction
• Comfort discussing dating, relationships, sexuality and personal goals in a professional, confidential setting
• Ability to manage yourself in a remote role, with flexibility to meet prospective clients when it suits them
• Knowledge of or lived experience within the LGBTQ+ community, and a commitment to inclusive, non-discriminatory practices
• Comfortable being on camera and representing a company publicly through social media and media opportunities

Preferred

• Background in sales management or leadership, including pipeline management and performance tracking
• Experience training or coaching clients or team members on services, processes, or best practices
• Experience creating or appearing in social media content
• Experience with podcasts, interviews, television, or other media appearances
• Strong personal presence and ability to communicate confidently on camera



• Fully remote position
• Uncapped earning potential through tiered commission
• A small, collaborative, mission-driven team
• The chance to help people find meaningful, lasting connections
• 1099 independent contractor role
• Opportunities to represent the brands through social media and media appearances

To apply, please send your resume and a cover letter describing your sales and matchmaking industry experience, as well as any relevant experience with social media, public speaking, interviews, or media appearances, to View email address on click.appcast.io