Confessions with Jess and Cindy

Balancing Two Businesses with Jennie Armstrong


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Jennie Armstrong, founder of Wild Awake and Delve, started her second business when she kept getting people who weren’t her core audience asking for her services. 

Jennie shares the behind-the-scenes journey of transitioning from a solopreneur to building a thriving consulting firm and online program - under the banner of two brands. Discover her strategies for attracting ideal clients, creating irresistible offers, and managing a remote team - all while serving as an elected state representative.

Key Highlights:

  • Understand Jennie's decision-making process for hiring employees versus subcontractors as her business expanded.
  • Learn her proven tactics for generating a consistent pipeline of clients through relationship-building and word-of-mouth marketing.
  • Gain insights into effectively onboarding and leading a remote team aligned with your vision and values.
  • Explore the systems and processes she implemented to facilitate growth while maintaining quality and work-life balance.
  • Discover her candid confessions about the challenges, lessons learned, and privileges that enabled her entrepreneurial journey.

Find Us Online:  https://www.confessionswithjessandcindy.com


Connect with Jennie:

Twitter: https://twitter.com/JennieForAlaska 

LinkedIn: https://www.linkedin.com/in/jenniemarmstrong/ 

Facebook: https://www.facebook.com/jenniemariearmstrong 

Instagram: https://www.instagram.com/wild_awake_creative/ 

Delve: https://www.delveforgood.com/ 

Wild Awake: https://www.wildawakecreative.com/ 

The Legacy Collective: https://www.wildawakecreative.com/legacy 


Connect with Cindy:

Cindy Wagman Coaching: cindywagman.com

Fractional Fundraising Network: fractionalfundraising.co/

LinkedIn: ca.linkedin.com/in/cindywagman


Connect with Jess:

Out In the Boons: outintheboons.me

LinkedIn: linkedin.com/in/jesscampbelloutintheboons/



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Confessions with Jess and CindyBy Cindy Wagman and Jess Campbell

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