B2B Event Sales Representative

CTFlea Events creates curated shopping experiences that bring local Connecticut makers, vendors, food businesses, and small businesses directly into senior communities and workplaces.

We are expanding two event programs:

• Resident Shopping Socials for nursing homes, assisted-living communities, senior centers, retirement communities, and rehabilitation facilities
• Workplace Shopping Socials for corporate offices, office buildings, property managers, employee-appreciation programs, and corporate events

We are looking for a confident, professional salesperson to help introduce these programs to organizations throughout Connecticut and manage prospective clients from the first conversation through the completed sale.

This is a remote, commission-based sales position with a flexible schedule. You will be responsible for researching potential clients, identifying the appropriate decision-makers, conducting outbound outreach, presenting our event programs, following up with prospects, and helping close paid event bookings.

Direct phone outreach will be the primary sales method, supported by email and LinkedIn outreach. You will work closely with CTFlea Events owner William Jackson during sales meetings, proposals, and account development.

This is not an appointment-setting-only position. The selected representative will remain involved throughout the complete sales process and continue managing relationships with the accounts they bring in.

• Research nursing homes, senior-living communities, corporate offices, office buildings, property-management companies, and other potential Connecticut clients
• Identify the person responsible for activities, employee engagement, tenant programming, community events, or event purchasing
• Make professional outbound sales calls using a CTFlea-provided Google Voice number
• Supplement phone outreach with personalized emails and LinkedIn messages
• Introduce and explain CTFlea’s Resident Shopping Social and Workplace Shopping Social programs
• Learn each prospect’s event needs, audience, timing, budget, and approval process
• Schedule and participate in virtual sales meetings with the owner of CTFlea Events
• Send pitch materials, package information, pricing, and follow-up communications
• Maintain consistent follow-up until the prospect makes a decision
• Help manage proposals, questions, objections, and the closing process
• Build long-term relationships that lead to repeat event bookings
• Continue managing accounts after the first sale
• Maintain accurate notes, prospect statuses, communications, and next steps in the company’s lead tracker or CRM
• Communicate professionally and represent CTFlea Events positively at every stage of the sales process

The ideal candidate is confident on the phone, friendly, organized, professional, persistent, and comfortable managing a complete sales process.

Previous sales experience is strongly preferred. Experience in B2B sales, event sales, appointment setting, senior living, hospitality, property management, corporate services, or account management is helpful but not required.

Applicants should have:

• Strong phone communication and relationship-building skills
• The ability to confidently contact businesses and decision-makers
• Previous sales or business-development experience
• The ability to explain a service clearly and persuasively
• Professional written communication skills
• Strong follow-up and account-management habits
• The ability to research companies, facilities, and decision-makers independently
• The confidence to participate in sales meetings and help close deals
• Reliable internet access and a professional remote-work environment
• The ability to organize leads and document sales activity
• A results-focused and self-motivated work style

Knowledge of Connecticut businesses, senior communities, office buildings, and local markets is strongly preferred. Connecticut residency is preferred but not required.

Experience: Previous sales experience strongly preferred

This is a commission-only position with uncapped earning potential.

Commission is paid on event revenue received by CTFlea Events from accounts originated, assigned, and actively managed by the sales representative.

The representative can also continue earning commission from repeat bookings for accounts they actively manage while working with CTFlea Events.

There is no fixed hourly schedule. The representative may work part time or full time and may hold another job, provided it does not create a conflict of interest or interfere with their CTFlea responsibilities.

Applicants must be comfortable working in a performance-based, commission-only sales role.

• A CTFlea Google Voice business phone number
• Professional pitch booklets and sales materials
• Event packages and pricing information
• Email outreach templates
• Support with lead lists and prospect research
• Direct support from the owner during meetings, proposals, and closing conversations
• Ongoing commission opportunities through repeat client bookings
• A flexible, fully remote work structure

The position will begin with a 30-day trial period.

During the trial, performance will be evaluated based on:

• Consistent outbound sales activity
• Quality of prospect research
• Conversations with qualified decision-makers
• Sales meetings scheduled
• Proposals or pricing discussions generated
• Follow-up consistency
• Accuracy of lead tracking
• Professional communication
• Paid events booked or a strong, verifiable sales pipeline

A qualified prospect should involve someone who can approve, recommend, coordinate, or directly influence an event purchase.

• Fully remote
• Flexible schedule
• Connecticut sales territory
• Part-time or full-time availability
• Most calls should be completed during normal business hours when organizational decision-makers are available

This is an opportunity to help grow a Connecticut-based event company while introducing local shopping experiences to senior communities, workplaces, employees, residents, families, and staff throughout the state.

The right person will have the freedom to manage their own schedule, build recurring client relationships, and earn ongoing commission from successful accounts.