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

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

Department: Retail Sales

Location: Chicago

This is not a charter sales job. Flight Club changes the math by offering a recurring relationship backed by a product that has no real equivalent in the market. Members stay because the experience is genuinely better, not because they’re locked in. As an Advisor, you are backed by Silver Air’s own FAA Part 135 certificate, in‑house fleet, dedicated Trip Management team, in‑house marketing professionals, a full‑service agency, and Hub Spot CRM with AI integration.

When your client flies, you own the relationship on a platform that delivers.

The compounding effect is real: every member you add generates recurring flight activity, referrals, and lifetime value that a transaction‑based model structurally cannot. 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. 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.

• 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

• 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

• 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

• 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 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 (Hub Spot preferred)

• Prior Part 135 aviation, charter, or private jet brokerage experience
• Passion for aviation, travel, and the…