Meet Our Team

Alyssa Olerud

Alyssa Olerud

Founder & CEO
Social media and personal branding for business owners and professionals | Trained 500+ on authentically selling online

FOUNDER & CEO

Alyssa Olerud

Alyssa Olerud is the Founder and CEO of Fearlyss Media, where she empowers business owners and professionals to share their stories and connect with their audiences on social media.

Before diving into entrepreneurship, Alyssa pioneered a remote program for a nationwide sales team, teaching them to leverage social media to expand their territories. Results boasting a 24% increase in success metrics and since then, she’s trained hundreds of sales reps on how to best utilize social media and works with business owners to manage their social media presences.

She lives by the philosophy that social media doesn’t need to be complicated; rather, it’s a powerful tool for finding your next best client. And if anyone knows a thing or two about balancing complexity, it’s her — juggling the chaos of raising two toddlers while fearlessly navigating the business world.

Alyssa is a New York native who now calls North Carolina home. She’s an avid reader, a die-hard sports fan who started her career working for the New York Yankees and Philadelphia Phillies, and someone who’s never shied away from dreaming big.

Lauren Jacaruso

Lauren Jacaruso

Social Media Manager
Lauren graduated from Emerson College in 2013 where she was a Division III Collegiate Softball player. She earned her degree in Marketing Communications and a minor in Business Studies, both with a specialization in entertainment. In 2021, she earned an MBA in Data Analytics from Louisiana State University - Shreveport. Lauren is an innovative marketing professional that has accrued ten years of experience working with national brands and athletes. Eight of those years took place within the professional baseball industry.
Josh Olerud

Josh Olerud

Growth Advisor
With over 18 years of experience in sports business leadership roles, Josh Olerud is a seasoned executive adept at driving strategic growth initiatives, business development, operations management, sales, and marketing. He currently serves as the Advisor for Strategic Growth here at Fearlyss Media, where he partners with the team to develop and implement strategies to propel the company's expansion. Josh is the Senior Manager of Business Development at Tar Heel Sports Properties, where he was creates strategic partnerships that tie together the community and Tar Heel athletics. Josh's extensive experience also includes successful tenures as the President and Chief Operating Officer of the Scranton/Wilkes-Barre RailRiders baseball team from 2015 to 2019. Before that, he spent five years as the Executive Vice President and General Manager of the Potomac Nationals, managing day-to-day operations, sales, marketing, and staff leadership.

Personal brand and social media strategy for business owners and professionals

Services

➤ Social Media Account Audit and Strategy

➤ Social Media Management

➤ Content Creation

➤ Social Media Training & Seminars

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