Director of Community & Events

Trajectory Recruiting LLC.; Freehold (NJ); On-site; USD 135,000 - 165,000; Full time

Benefits offered by this job

Health & Wellness

401(k) retirement plan with company

PTO 3 weeks

Annual performance bonus

Job summary

Trajectory Recruiting LLC in Freehold, NJ is seeking a strategic Director of Community & Events to transform a community into a continuous, high-impact business asset. You will lead the flagship conference, executive cohorts, and roundtables, moving beyond one-off events to long-term value creation.

This leadership seat demands defining the membership model, establishing active member metrics within 90 days, and building an execution capability with the existing team.

Qualifications

• 7+ years of progressive leadership in community management, large-scale events, executive membership programs, or cohort operations.

Responsibilities

• Define the membership value proposition, structure, and persona segmentation.
• Establish active member definitions and track health KPIs during first 90 days.
• Own full P&L, budget, agenda architecture, and attendee experience for flagship conference (450+ attendees).
• Oversee executive mastermind sessions and AI Accelerator programs.
• Lead cross-border operations with distributed team members across US and offshore locations.
• Partner with Sales and Marketing while owning the community brand.

Skills

Leadership

P&L ownership

Executive presence

Cross-functional collaboration

Distributed teams

Job description

Location: Freehold, NJ (Onsite 4-5 days/week)

Travel: Approximately 25%

Employment Type: Full-time

Compensation: $135,000 – $165,000 base salary + annual performance incentive

About the Opportunity

We are an established Master Managed Service Provider (MSP) and B2B technology services organization with a global delivery footprint of approximately 900 team members across the US and internationally. Alongside our core managed IT, co-managed, and staffing solutions, we operate dedicated SaaS platforms and specialized AI services for the MSP ecosystem.

Our industry community brings together MSP owners, founders, and executives through an annual marquee conference, an AI accelerator cohort, and exclusive executive mastermind peer groups.

We are hiring an entrepreneurial, strategic Director of Community & Events to shift our focus from organizing one-off calendar events to establishing community as a continuous, high-impact business strategy. In this role, the community is the central asset; our flagship conference, executive cohorts, and roundtables are the instruments used to engage, grow, and retain it year-round.

The Reality of the Seat

This is not a steady-state or purely logistical coordination role. There is no pre-existing playbook, no turnkey execution team waiting, and no pre-instrumented community data baseline. Your mandate in Year 1 is to define the membership model, instrument engagement and retention metrics from the ground up, and develop an execution capability utilizing our existing coordinator-level team, cross-functional partners, and specialized agency/vendor support.

If you thrive when navigating ambiguity and love building sustainable programs from a blank canvas, this is an exceptional leadership opportunity.

What You Will Own

• Community Strategy & Year-Round Engagement: Define the membership value proposition, structure, and persona segmentation. Create continuous touchpoints, digital engagement channels, and advocacy programs so the community thrives between events.
• Instrumentation & Metrics: Establish the definition of an active member, instrument engagement and retention baselines during your first 90 days, and track community health KPIs.
• Flagship Industry Conference: Own the full P&L, budget, agenda architecture, speaker strategy, venue operations, and attendee experience for our premier annual event (450+ attendees / 250+ MSP businesses).
• Executive Peer Groups & Cohorts: Oversee the structure, recruitment, and delivery of our executive mastermind sessions and quarterly AI Accelerator programs.
• Cross-Border Leadership: Build operational consistency and standard operating rhythms, leading and mentoring distributed team members across the US and offshore locations.
• Cross-Functional Collaboration: Partner with Sales (on sponsor enablement and value realization) and Marketing (on demand generation), while maintaining full strategic ownership of the community brand.

What We Are Looking For

• 7+ years of progressive leadership in community management, large-scale events, executive membership programs, or cohort operations.
• Proven P&L ownership: Direct financial accountability for an event series, membership franchise, or program budget (not merely administrative expense tracking).
• Demonstrated builder mentality: A documented track record of designing, scaling, or fundamentally transforming a community or program from an ambiguous starting point.
• Experience leading distributed, cross-cultural teams across time zones, alongside a proven ability to influence matrixed stakeholders across Sales and Marketing.
• Executive presence: Exceptional communication skills and comfort serving as an authentic, credible face of the community with business owners and C-level executives.
• Industry background: Experience within the MSP channel, IT services, or B2B SaaS is strongly preferred (though senior community craft from adjacent B2B professional associations will be considered).
• Familiarity with the Entrepreneurial Operating System (EOS) or similar execution frameworks is a plus.
• Work arrangement: Ability to work on-site at the office in Freehold, NJ five days per week, with ~25% domestic travel.
• Base Salary: $135,000 – $165,000 per year
• Incentive: Annual performance bonus tied to agreed-upon scorecard targets
• Health & Wellness: Comprehensive medical, dental, and vision insurance
• Retirement: 401(k) retirement plan with company match
• Paid Time Off: 3 weeks of PTO in Year 1, increasing to 4 weeks starting Year 2, plus standard company holidays
• Eligibility: US benefits eligibility begins after 30 days of employment