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

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

Department: Retail Sales

Employment Type: Full Time

Location: Chicago

Compensation: $300,000 - $1,200,000 / year

This is not a charter sales job.

Why Flight Club Is the Right Move for an Experienced Broker

Flight Club changes the math. When you enroll a member, you are opening a recurring relationship backed by a product that has no real equivalent in the market. There is no upfront cost to the client, no rigid contract, and 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 are 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 Hub Spot CRM with AI integration. The platform is Wyvern Wingman PRO certified and IS‑BAO Stage 3 compliant, delivering the highest independent safety ratings in private aviation.

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 cannot match. Top Advisors earn 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.

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

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 Hub Spot 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

• 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…