Fixed — third person, agency framing.
Director of Membership Sales
Remote (EST+ hours) · Full-time · Base + uncapped commission
Our client is a high-touch travel concierge company (delivered over WhatsApp) serving founders, investors, and senior execs. The model is already proven: multi-million monthly sales, very high retention, notable customers, recent raise led by a top-tier fund.
The problem
The company generates hundreds of qualified leads a month through ads, referrals, and partnerships. AI-driven onboarding converts leads to trial at a rate well above average. What's missing is someone to take that trial and close it. Trial-to-member conversion is in the single digits today, it should be 30%, because that's what happens when someone responds fast and isn't afraid to get on the phone.
What the role owns
Speed to lead: personal WhatsApp message in under 5 minutes, quote in hand in under an hour
Trial activation: takes the context AI already gathered and builds the relationship through to the first trip request
Follow-up until there's an answer: minimum 3 touches over 30 days, most deals die from silence, not rejection
Sales dashboard at inbox zero: every lead with a next step and a date
Feedback upstream: reports what converts and what doesn't back to the team
Who they're looking for
A closer. A real sales closer. Has sold something hard before and loves the game
Lives on WhatsApp: fast response feels natural, not heroic
Self-starter: takes a high-level brief and comes back with results, not questions
Motivated more by uncapped commission than a high base
Genuinely loves travel: it shows within two messages
Uses AI daily, personally and professionally
Must have: travel/flight sales experience, deep miles/points knowledge, has built AI-driven sales systems before.
Compensation
Base: $30K–$40K
Uncapped commission + upside tied to travel revenue
OTE: $100K+ year one at moderate success, $150K+ at strong success, no ceiling
Fully remote, covering EST hours
Why join
Reports directly to the company's COO. Works directly with cofounders and C-suite. Real product-market fit, high-profile customers, fast growth, and a clear operational problem waiting for an owner. Annual company-paid offsite.
Skills Required
- Travel/flight sales experience
- Deep miles and points knowledge
- Has built AI-driven sales systems before
- Proven closer with experience selling complex/high-value services
- Lives on WhatsApp and responds very quickly
- Uses AI daily, personally and professionally
- Self-starter who executes from high-level briefs
- Motivated primarily by uncapped commission
- Genuinely loves travel and conveys that quickly
- Able to work EST hours (fully remote)
What We Do
Ambilio is an enterprise AI product and consulting firm that helps organizations build AI capabilities and move from strategy to live deployment. It serves as one accountable partner across assessment, product development, analytics, and adoption, with expertise in generative AI, artificial intelligence, and AI consulting. The company combines technology and advisory services to support enterprise AI implementation and practical, measurable business outcomes.
