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Strategic travel, thoughtfully executed.

Points, miles, and credit strategy – for people who want to use them well.

ClearSkies is a boutique advisory practice helping individuals and families use points, miles, and credit strategy with clarity and discipline.


We help thoughtful, financially savvy clients turn the money they're already spending into exceptional travel - often achieving premium flights and luxury hotels for a fraction of the cash price. We focus on strategy, clarity, and intentional decision-making, not hacks or hype.

Retained Point Value

Preserved points compound into future travel.


Transfer ratios vary.
Award pricing fluctuates.
Booking channels change outcomes.
Credits and benefits alter real value.


Some people dive deep into the analytics.
Others prefer not to.


ClearSkies exists at the intersection.
We do the analysis.
You make clear, confident decisions.

Same hotel. Same night.
72,000 points → 29,653 points + property credit
42,347 points retained
Two travelers. Alternate transfer partner utilized.
30,000 Membership Rewards retained
Points + loyalty benefits. Structured intentionally.
Alternate booking channel → Status recognized
Points retained + Points earned
Complex itinerary. Multiple currencies.
Original plan: 147,000 + miles in economy
Reframed routing + alternate transfer partner.
Fewer connections. Less cash.
Points preserved. Optionality intact.

Just because you can afford it
doesn't mean you should pay cash.

Many ClearSkies clients can easily afford premium cabin flights and luxury hotels. What they question is whether paying cash for those experiences is the best use of money - especially when the same outcomes can often be achieved through thoughtful use of points and incentives.


ClearSkies exists to help clients make those decisions deliberately, preserving cash for what matters most while still traveling exceptionally well.

Our Approach

Membership Options

ClearSkies is offered through three structured tiers:

Essentials

Do it yourself
Best suited for individuals who want a disciplined framework and a more intelligent way to research.
Includes:
Learning & Strategy
  • Foundational strategy webinars
  • Core decision frameworks
Tools & Support
  • Decision checklists
  • Monthly office hours
  • Case studies and real-world examples

Advisor

Do it with me
Designed for individuals or households who already understand points - and want structured judgment on when and how to deploy them.
Includes Essentials+ :
CUSTOMIZED & PLANNING
  • Personalized card sequencing guidance
  • Spend and redemption strategy alignment
GUIDED DECISION MAKING
  • Ongoing decision support
  • Periodic strategy reviews
  • Applied tools & calculators

Concierge

Do it for me
Structured engagement for those who prefer proactive oversight within defined scope.
Includes Advisor+ :
FULL-SERVICE EXECUTION
  • Award search & booking support
  • Booking path evaluation
  • Priority response
ACTIVE OVERSIGHT
  • Transfer and currency analysis
  • Annual fee review & offset
Jennifer Franklin Signature

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

FAQ

ClearSkies provides strategic advisory services related to travel rewards and credit strategy. We do not operate as a traditional travel agency, sell packaged travel, or issue tickets directly. Our role is to evaluate options and guide decisions within the scope of your membership.

No. ClearSkies does not accept affiliate commissions from credit card issuers or travel providers. Recommendations are made independently and based solely on client strategy and fit.

Retained point value refers to points preserved by choosing a more efficient booking path. When an alternate transfer partner, booking channel, or structured approach reduces the number of points required for the same outcome, those unused points remain available for future travel.

Yes. Upgrades may be made at any time and are prorated for the remainder of your billing cycle. Downgrades may be scheduled at any time and will take effect at your next renewal. Current billing periods are not prorated. Concierge engagements are structured for a defined term and may be upgraded, but not reduced, mid-engagement.

Yes. You may cancel renewal at any time. Access and services remain active through the end of your current billing or engagement term. Fees already paid are non-refundable.

Concierge engagements are structured for a defined term. If circumstances change, we will clarify remaining scope and access within the engagement period. Fees are non-refundable once an engagement begins.

Yes. Information about points and miles is widely available. What is less available is judgment. Program rules change. Transfer ratios shift. Availability varies. Advice online is often fragmented or contradictory. ClearSkies exists to translate complexity into disciplined action - so you do not need to spend your time assembling, testing, and second-guessing every decision.

Response timing depends on your membership tier. Concierge members receive priority response within the scope of their engagement.

No. Reward programs, transfer ratios, and availability are controlled by third parties and may change at any time. ClearSkies provides structured analysis and guidance, but specific outcomes cannot be guaranteed.

Concierge is designed for individuals or households who prefer proactive oversight within defined scope and do not wish to manage award searches or transfer strategy independently.

No. ClearSkies Concierge does not collect, store, or require access to sensitive personal information such as Social Security numbers, dates of birth, or credit card details.

For application support or booking guidance, we may offer live screen share sessions to walk you through the process step-by-step. During these sessions, you remain in full control — you enter all personal and payment information directly into the relevant websites yourself.

This approach is intentional. It protects your privacy and ensures that your sensitive information stays entirely in your hands.

ClearSkies provides guidance and strategy — you execute securely on your own accounts.