Pick the engagement
that fits your stage.
Three ways to work together — from a focused strategy session to an ongoing fractional advisory partnership. No discovery call required to start.
Access the playbook, AI news, and community
Ongoing content and community access through a membership subscription. Choose the tier that fits your needs.
Insider Monthly
Insider
$49/month
Access to the content library, office hours recordings, and curated AI news. A great way to stay current without a deep commitment.
- ✓ Full content library access
- ✓ Office hours recordings
- ✓ Curated AI news & analysis
- ✓ Playbook Chapter 1 (free preview)
Insider Annual · Best Value
Insider Annual
$499/year
Everything in monthly plus the complete 8-chapter playbook with a drip schedule. The best way to transform your organization methodically.
- ✓ Everything in Insider Monthly
- ✓ Complete 8-chapter playbook (drip schedule)
- ✓ Chapters 1-2 at signup, 3-4 at month 2, etc.
- ✓ Future playbook updates included
Advisory Circle
Advisory Circle
$200/month
The complete experience: full playbook with immediate access, live group calls, private Slack community, and a quarterly 1:1 session with Jess.
- ✓ Everything in Insider Annual
- ✓ Full playbook — immediate access (no drip delay)
- ✓ Live monthly group calls
- ✓ Private Slack community
- ✓ Quarterly 1:1 session with Jess
Need hands-on advisory?
For teams that need direct strategic guidance — from a focused session to an embedded partnership.
Tier 1
Strategy Session
$1,500
3 hours · Valid 60 days
A focused deep dive on one topic — board prep, roadmap review, pricing model design, or an assessment debrief. The fastest way to get expert eyes on your specific challenge.
- ✓ One focused topic or question
- ✓ Pre-session intake form
- ✓ Written summary after the call
- ✓ Complete playbook PDF ($550 value)
- ✓ Calendar booked within 1 business day
Tier 2 · Most Popular
Transformation Sprint
$7,500
15 hours · Valid 90 days
Structured project work with a defined deliverable — an AI strategy roadmap, a team capability plan, a pricing model design, or a board-ready presentation. Use hours flexibly across sessions.
- ✓ Defined deliverable agreed upfront
- ✓ Hours used flexibly (1–3 hr sessions)
- ✓ Async Slack/email support between sessions
- ✓ Final deliverable document included
- ✓ Complete playbook PDF ($550 value)
Tier 3
Fractional Advisor Retainer
$8,000/month
Up to 16 hours/month · 3-month minimum
Embedded ongoing strategic partnership. A consistent senior voice in your planning cycles, board reporting, and key decisions — without the cost of a full-time executive hire.
- ✓ Monthly recurring strategy sessions
- ✓ Board-level reporting support
- ✓ Priority async access (Slack/email)
- ✓ Complete playbook PDF ($550 value)
- ✓ First month billed upfront · renews monthly
Common questions
What happens after I purchase?
You'll receive a payment confirmation from Stripe. Jess will follow up within one business day with a calendar link and a brief intake form to make sure the time is focused and valuable.
Can I start with an assessment and then book a session?
Yes — and that's the recommended path. Your assessment score gives us a concrete starting point, so the advisory time is spent on action rather than diagnosis.
Not sure which tier is right?
Start with a Strategy Session. It's the lowest-commitment way to see if there's a fit — and most clients who do come back for a Sprint or Retainer.