Private Jet Advisor - Gold Coast, Lincoln Park & North Shore, IL

Job Description

Job Description

Description

This is not a charter sales job.

Why Flight Club Is the Right Move for an Experienced Broker

If you've spent years in charter brokerage, you already know the model's ceiling. Every month resets. Every client relationship you've built lives inside a product that's identical to what three competitors quoted them yesterday. You're good at what you do — but the structure works against you.

Flight Club changes the math.

When you enroll a member, you're not closing a transaction — you're opening a recurring relationship backed by a product that has no real equivalent in the market. No upfront cost to the client, no rigid contract, no commodity pricing war. The friction that kills charter conversions doesn't exist here. Members stay because the experience is genuinely better, not because they're locked in.

As a Flight Club Advisor, you're not a middleman anymore. You're backed by Silver Air's own FAA Part 135 certificate, in-house fleet, dedicated Trip Management team, three in-house marketing professionals, a full-service agency, and HubSpot CRM with AI integration — and a platform that is Wyvern Wingman PRO certified and IS-BAO Stage 3 compliant, the highest independent safety ratings in private aviation. When your client flies, you're not hoping an operator delivers. You own the relationship on a platform that delivers.

The compounding effect is real: every member you add to your book generates recurring flight activity, referrals, and lifetime value that a transaction-based model structurally cannot. Top Advisors are earning well into the high six figures, with seven-figure potential for those who build a strong book of recurring business.

Flight Club is Silver Air's invitation-only private jet membership. Private Jet Advisors don't chase tail numbers, quote trips, or manage logistics. That's handled. Their role is to build trusted relationships with ultra-high-net-worth clients and become their long-term aviation advisor.

In Chicago, that means being present where serious wealth and relationships converge — Gold Coast private wealth circles, Lincoln Park luxury real estate networks, North Shore family offices, private clubs, philanthropic events, and executive communities across Winnetka, Glencoe, Wilmette, and Lake Forest.

The platform is built. We need the right person to leverage it.

Great Place to Work Certified. High performance. No chaos. Your book. Your clients. Your career.

What You'll Do

Build Your Book

• Prospect and develop relationships with ultra-high-net-worth individuals, family offices, executives, and entrepreneurs across target markets — through your existing network, referral channels, and strategic outbound
• Represent Flight Club at private events, charity galas, real estate gatherings, yacht shows, and luxury lifestyle activations where your ideal clients already are
• Convert qualified inbound leads generated by our marketing team into enrolled Flight Club members

Sell the Membership, Not the Flight

• Lead consultative discovery conversations that uncover a prospect's travel patterns, lifestyle priorities, and aviation needs — then position Flight Club as the intelligent solution
• Guide prospects through the Flight Balance funding process with complete transparency — no pressure, no fine print, no surprises
• Articulate the full Flight Club value proposition: invitation-only access, tail-specific aircraft selection, Mechanical Recovery Guarantee, curated one-ways, and a luxury lifestyle partner network most clients didn't know existed

Own the Relationship

• Serve as the primary point of contact for every member in your book — responsive, proactive, and relationship-first
• Introduce members to Flight Club's lifestyle partner network — private clubs, villas, yachts, bespoke concierge, and exclusive events — before they have to ask
• Drive referral pipeline through member experience that speaks for itself

Operate Like a Business

• Manage your HubSpot CRM pipeline with precision — every activity logged, every follow-up timed, every opportunity tracked
• Coordinate with the marketing team on campaigns, activations, and member events
• Contribute to the rollout of Flight Club's member travel program — curated group experiences for members flying together

Skills, Knowledge and Expertise

• 5+ years in a high-performance sales role - luxury, real estate, wealth management, hospitality, or executive services
• Existing network of high-net-worth contacts that fly private — family offices, executives, real estate principals, or wealth advisors
• Demonstrated track record of meeting or exceeding revenue targets
• Experience building relationships with affluent or ultra-high-net-worth clientele
• Natural consultative selling style — you listen first, pitch second
• Exceptional verbal and written communication skills
• Self-starter comfortable operating without a script
• CRM proficiency (HubSpot preferred)

Highly Preferred:

• Prior part 135 aviation, charter, or private jet brokerage experience
• Passion for aviation, travel, and the luxury lifestyle space

Benefits

What You Earn

• Base salary + uncapped commission — your book grows, your income grows, no ceiling
• Performance bonuses on Aircraft Management deals (PureJet Management) 
• 5% matching 401(k) / Roth
• Cell phone allowance

What You're Covered By

• Fully paid health insurance — for you and your entire family
• Mental health support
• Travel insurance + pet insurance
• Wellness programs and work-life balance initiatives
• Generous personal development and employee assistance programs

Who You're Joining

 

A Team of people who chose Silver Air because the platform is real, the culture is earned, and the opportunity compounds. We're Great Place to Work Certified because we actually work at it.

We also invest in your success the way most companies don't. Client entertainment, club memberships, golf outings, gifts, and relationship-building events are supported — not out of pocket. When you're ready to pursue a corporate flight department or a high-value pitch, our executives show up with you. We don't just hand you a product and wish you luck; we help you open doors that take most advisors years to crack on their own.