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The Strategy Circle Workshop

The Strategy Circle

A leadership retreat for women founders who are done spinning wheels and ready to scale with clarity and confidence.

The Strategy Circle is a one-day, high-impact retreat for women entrepreneurs who want to step back, think strategically, and take aligned action toward meaningful growth.

This isn’t a conference.
It’s not a webinar.
It’s a curated experience for ambitious women who want to strengthen their business models, understand their numbers, and map out a path that supports their vision, their life, and their leadership.

Our retreat takes place at CO in Rhinebeck, NY, a beautifully designed studio space surrounded by nature. It’s the ideal setting to step away from the noise, reset your thinking, and focus on the future you’re building. The day includes gourmet meals, curated strategy materials, and a post-retreat follow-up to support your next steps and keep your momentum going.

The retreat is led by Dallas Gilpin, founder and CEO of Shale Hill Strategies and Shale Hill Hospitality Group. With a background that blends financial expertise from her years at Goldman Sachs and hands-on success as a business owner, Dallas brings a clear, grounded approach to growth. She helps founders cut through the noise, focus on what matters, and build businesses that are both sustainable and aligned with their values.

With expert guidance, hands-on planning, and meaningful peer connection, you’ll leave with fresh energy and a real plan to move forward with confidence.

What You'll Walk Away With

  • A clear, customized growth plan rooted in your vision

  • A practical understanding of your numbers (without overwhelm)

  • Refined pricing, offers, or systems that support momentum

  • A strategic lens on what to build, cut, or shift in your business

  • Confidence in your role as CEO and space to make bold decisions


Reserve your seat and join a room of women who are ready to lead with intention, not overwhelm.

Your registration includes gourmet meals, strategy materials, and a post-retreat follow-up to keep the momentum going.

Retreat Agenda:

9:00 – 9:30 AM
Arrival, Coffee, and Intros
Prompt: What are you here to unlock in your business?

9:30 – 10:45 AM
Session 1: Your Business Engine

  • Strategy and vision mapping

  • Business model clarity

  • Identifying gaps between goals and operations

10:45 – 11:00 AM
Break + Guided Prompt
Prompt: What is currently blocking my next level?

11:00 – 11:15 AM
Sharing + Unblock Tools

11:15 – 12:15 PM
Session 2: Know Your Numbers

  • Profit and loss essentials

  • Cash flow check-in

  • Pricing, cost management, and owner pay

  • Personal finance as a founder

12:15 – 1:00 PM
Lunch + Networking
Prompt: What’s one decision you’ve been avoiding?

1:00 – 2:30 PM
Session 3: Growth Strategy Lab

  • Identify your growth lever (revenue, ops, marketing, team)

  • Decide what to build, fix, or cut

  • Open coaching and group “hot seat” strategy mapping

2:30 – 3:00 PM
Break + Journaling/Reflection
Prompt: What would it feel like to run my business with more ease?

3:00 – 4:00 PM
Session 4: Systems for Sanity

  • Simple dashboards and KPIs

  • Delegation structure

  • Tech stack and automation tools, including AI

  • Weekly CEO workflow

4:00 – 5:00 PM
Closing Circle + Commitments + Wine and Snacks

  • Share one commitment for the next 30 days

  • Connect and celebrate with fellow founders

Upcoming Session:
Date: September 29, 2025
Location: CO Rhinebeck, NY
Capacity: 10 participants only
Investment: $500 (Includes Gourmet Meals, Strategy Materials, and a Post-Retreat Follow-Up)