Travel Oregon Why Guides

Spring 2026 Cohorts

Welcome to Pregame!

Congratulations, you've been awarded a spot in the Why Guides Business Accelerator program!

The content covered over the three month period will focus on leveling up your business across brand, marketing, sales, and operations. At the end of the program, you will have the skills to determine your own strategy and actions to sustain your own success.

How to Get the Most Out of This Program

This program is valued at $3000 and is subsidized through Travel Oregon's Why Guides program, posing no financial cost to you. In return, you must make the following commitments:

  • Show up! Attend your weekly Home Team, the one-hour virtual coaching session with fellow guides in the cohort, led by your Pregame Coach. More info below.
  • Dive in! Commit at least one hour of your own time each week to virtual content and action steps.
  • Level up! Post your questions and advice in the group chat throughout the week.
  • Keep it real! This is a pilot program and participating businesses will be required to complete an evaluation survey at program completion.

Cohort Schedule & Curriculum

To access your Home Team cohort session and content modules, log in to Pregame on Demand.

Cohort 1

Team Devil's Lake

Demand, Sales, and Bookings
Tuesdays @ 9am
w/ Coach Ciara

Week 1 2/17 Diagnostic + Goal Setting
Week 2 2/24 Clarify Target Audience
Week 3 3/3 Unique Value
[skip week - Oregon Tourism Conference]
Week 4 3/17 Products & Pricing
Week 5 3/24 Sales Process
Week 6 3/31 First Impressions
Week 7 4/7 Calls to Action
Week 8 4/14 Generating Leads
Week 9 4/21 Overcoming Objections
Week 10 4/28 Upselling, Renewing, Reselling
Week 11 5/5 Systems & Habits
Week 12 5/12 Capstone

Cohort 2

Team Devil's Punchbowl

Brand Clarity & Market Positioning
Tuesdays @ 10am
w/ Coach Jen

Week 1 2/17 Diagnostic + Goal Setting
Week 2 2/24 Defining Brand
Week 3 3/3 Target Audience Synthesis
[skip week - Oregon Tourism Conference]
Week 4 3/17 Unique Value + Value Proposition
Week 5 3/24 Visual Brand
Week 6 3/31 Verbal Brand
Week 7 4/7 Service / Product Descriptions
Week 8 4/14 Website Strategy
Week 9 4/21 Content Types
Week 10 4/28 Content Calendar
Week 11 5/5 Integrating Your Brand
Week 12 5/12 Capstone

Cohort 3

Team Devil's Churn

Systems, Operations, and Strategic Focus
Tuesdays @ 12pm
w/ Coach Loren

Week 1 2/17 Diagnostic + Goal Setting
Week 2 2/24 Strategy vs Tactics
Week 3 3/3 Time Value
[skip week - Oregon Tourism Conference]
Week 4 3/17 Roles & Role Clarity
Week 5 3/24 Systems & Habits
Week 6 3/31 Managing for Results
Week 7 4/7 Communication Clarity
Week 8 4/14 Asking for Help
Week 9 4/21 Effective Meetings
Week 10 4/28 Return on Investment
Week 11 5/5 The Long Game
Week 12 5/12 Capstone

Meet Your Coaches

Ciara on a Horse

Ciara Pressler

Strategy, Sales, Scaling

Jen adventure

Jen Price

Brand, Marketing, Messaging

Loren dadding

Loren Castillo

Tech, Media, Digital

Pregame On Demand

Pregame On Demand is included with your Cohort! You now have 24/7 access to over 150 video modules, worksheets, and templates that show you how to level up your business faster and smarter.

Got questions? Visit the Why Guides community space to collaborate with other guides and get input from Pregame coaches!

Use the left menu to navigate between spaces, including access to your Home Team livestream.

DIYPR Course Bundle