Membership Options

ClearSkies is offered through three structured tiers:

Essentials

Do it yourself

$399 /yr

$49 /mo

– 32%

Yearly

Monthly

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

Best for you if:

You enjoy learning the mechanics yourself
You want structured frameworks & guidance
You're willing to do the searching and execution
You value clarity but prefer independence

Advisor

Do it with me

$1,499 /yr

$149 /mo

– 16%

Yearly

Monthly

For those who already understand points—and want structured judgment on earning and using them.

Includes Essentials+:

CUSTOMIZATION & PLANNING

Personalized card sequencing guidance
Spend and redemption strategy alignment

GUIDED DECISION MAKING

Ongoing decision support
Periodic strategy reviews
Applied tools & calculators

Best for you if:

You already search award space
You understand transfer partners and multiple currencies
You track balances and routing options
You sense when something feels inefficient—but want conviction before deploying 100,000+ points
You want structured judgment on high impact decisions

Concierge

Do it for me

$4,498 /yr (3 journeys)

$2,249 /6 mos (1 journey)

Yearly

Bi-annually

Structured engagement for those who prefer proactive oversight within a 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

Best for you if:

You value proactive oversight within defined scope
You prefer not to manage award searches independently
You want structured review of annual fees and card strategy
You appreciate disciplined execution without constant decision fatigue

Explore Inside ClearSkies

Inquire About Working Together

Client Experiences

1 / 5

What our clients say:

Jenn was a lifesaver when my original points flights were cancelled by the airline and I needed to find a new route, move points and find the elusive lie-flat seats. She was responsive, found custom options for my exact point availability and got me there quickly. She will be my first call anytime I look to maximize my points and miles.

Ricci T.

We already understood transfer partners and had booked award travel before, but ClearSkies helped us think about routing, flexibility, timing, and overall value at a completely different level.

Linda S.

I love just handing things over to Jenn and having her tell me exactly what to do to book the flights she finds!

Kathy P.

I had accumulated points but didn’t really have a plan for how to use them effectively. Jenn helped us organize everything into a clear strategy and was there to provide reassurance that saved me from overthinking the bookings.

Amanda S.

The biggest surprise was how personalized the experience was. ClearSkies didn’t just help us book trips... they helped us think ahead about future travel, card strategy, and how to evaluate trade-offs to further support our travel goals.

Julie B.

ClearSkies has helped us save a meaningful amount of money and points, but honestly, the time and mental energy saved was just as valuable.

Vince S.

Choose your engagement

Learn & Optimize

Guided Strategy

Concierge Support

Best for

Learning & Self-execution

Planning with guidance

Full stewardship

Commitment

Monthly / Annual

6 or 12 Months

Journeys

1 or 3 Journeys

Personalized strategy

Card opening/closing strategy

Flight optimization & hotel strategy guidance

Credit card referral participation

Price

$49/mo or $399/year

$149/mo or $1,499/year

$2,249 / 6 months or $4,498 / year **

* Annual plans include optional community referral-link participation.

** Engagement confirmed prior to payment.

Not sure which membership is right for you?

Inquire About Working Together

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.

Lorem ipsum dolor sit amet, consectetur adipiscing elit. Suspendisse varius enim in eros elementum tristique. Duis cursus, mi quis viverra ornare, eros dolor interdum nulla, ut commodo diam libero vitae erat. Aenean faucibus nibh et justo cursus id rutrum lorem imperdiet. Nunc ut sem vitae risus tristique posuere.

View PDF

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.

View PDF

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.

View PDF

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.

View PDF

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.

View PDF

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.

View PDF

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.

View PDF

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

View PDF

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.

View PDF

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.

View PDF

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.

View PDF

Membership Options

Essentials

Advisor

Concierge

Client Experiences

Essentials

Advisor

Concierge

What We’re Building Next

Bank Bonus Strategy

One-Off Award Search

YNAB Consulting

Join the waitlist

FAQ

Membership Options

Essentials

Advisor

Concierge

Client Experiences

Essentials

Advisor

Concierge

What We’re Building Next

Bank Bonus Strategy

One-Off Award Search

YNAB Consulting

Join the waitlist

FAQ

Is ClearSkies a travel agency?

Do you receive affiliate commissions?

What does "retained point value" mean?

Can I switch tiers?

Can I cancel?

Can I cancel a Concierge engagement early?

Isn't this information available for free?

How quickly will I receive support?

Do you guarantee specific point values or availability?

Who is Concierge best suited for?

Do you need access to my personal or financial information?

Join the Waitlist

Create your account

Welcome back

Concierge Plan