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Ongoing Stewardship for Complex Travel Decisions

Thoughtful, scoped support for defined travel objectives.

Concierge Support is designed for clients who value time, calm, and confident decision-making. We handle the most complex and high-impact elements of points travel - flights, lodging, and points strategy - so you don't have to monitor availability, second-guess decisions, or scramble when conditions change.

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This is not a transactional booking service.

It's an engagement focused on outcomes and stewardship over time.

Most clients come to Concierge after realizing they don't want to manage this themselves anymore.

Begin Engagement

What Concierge Includes

  • Personalized card strategy and application support
  • Proactive evaluation of booking paths
  • Transfer strategy guidance
  • Ongoing strategic oversight
  • Flight and lodging searches
  • Redemption assistance
  • Monitoring and re-optimization of booked flights
  • Priority response

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ClearSkies focuses on high-impact travel decisions: flights, lodging, and points strategy. Activity planning, ground transportation, and destination logistics are not included.

Where helpful, ClearSkies may share a short list of curated experiences aligned with your destination and travel style. This is provided for inspiration only; ClearSkies does not book or coordinate activities.

Engagement Structure

6-Month Engagement
Support for one defined journey – from planning through booking and refinement.

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12-Month Engagement
Support for up to three defined journeys, with ongoing optimization and oversight.

Scope and timing are confirmed before enrollment

Begin Engagement

Concierge engagements are intentionally limited and structured around travel complexity, optimization goals, and collaboration fit. We review each inquiry personally and confirm scope and next steps promptly.
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Why clients trust ClearSkies

  • Executive-level marketing & communications leadership (25+ years)
  • Financial services background; formerly Series 7 & 24 licensed
  • Disciplined management of a multi-card points portfolio
  • 10M+ points earned; 7.5M+ redeemed strategically
  • Philosophy of intentional wealth use
Read the full founder story
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My Membership
Current Plan:
Essentials
Advisor
Concierge
Includes:
Foundational strategy webinars
Core decision frameworks
Decision checklists
Monthly office hours
Case studies and real-world examples
Includes:
Spend & redemption strategy alignment
Applied tools & calculators
Ongoing decision support
Periodic strategy reviews
Personalized card sequencing guidance
Includes:
Award search & booking support
Booking path evaluation
Priority response
Transfer and currency analysis
Annual fee review & offset
Upgrade your plan
Advisor
Designed for those who understand points and want structured judgment on when and how to deploy them.
Spend & redemption strategy alignment
Applied tools & calculators
Ongoing decision support
Periodic strategy reviews
Personalized card sequencing guidance
Upgrade to Advisor
Concierge
Structured engagement for those who prefer proactive oversight within defined scope.
Award search & booking support
Booking path evaluation
Priority response
Transfer and currency analysis
Annual fee review & offset
Apply for Concierge
Billing & Payments

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