About Christina O'Leary

As the Owner, Founder, and CEO of Pivotal Success, a boutique marketing agency specializing in personal brand and startup development, Christina is dedicated to elevating the brands of small to mid-sized companies. She employs a detailed strategy known as SLIM ROLL™ Marketing, which encompasses content, communication, and storytelling techniques. 

In addition to her role at Pivotal Success, Christina is the Co-Founder and Executive Creative Partner at Sophia Health Tech, Inc. This innovative company offers a once-in-a-generation solution that fundamentally transforms how the world experiences healthcare through its S.O.P.H.I.A initiative. 

Christina also contributes her expertise as the Interim VP of Marketing at The Aspenwood Company, a senior living owner and management firm that features mid-luxury and luxury senior living properties. These properties are designed to blend elevated lifestyles with refined elegance, five-star hospitality, and world-class care. 

Before taking on her current positions, Christina spent nearly two decades at Spring Hills, LLC. She advanced from Director of Sales & Marketing to Vice President of Branding & Media, where her leadership drove exceptional growth and established a legacy of excellence in branding, integrated communications, storytelling, and marketing innovation. 

Christina is often likened to a Swiss Army Knife, as she embodies versatility across various roles. She is known for her reliability as a successful professional, her inspiring leadership, and her dedication as a mother of three.

Led social media efforts to enhance the online presence of one of the fastest-growing senior living operators in 2025, which also secured Third Place in the 2025 Aspect Marketing & Advertising Awards, presented by Senior Housing News and WTWH Media LLC, for the campaign "The Leadership Lift: Transforming Brand Presence Through Strategic Marketing Campaigns." Implemented a strategic plan that propelled a start-up from obscurity to an industry leader, achieving remarkable growth from $0 to $11M in just 30 months. Oversaw comprehensive marketing, media, and branding initiatives for 28 businesses, including assisted living, memory care, post-acute care, home health care, and various physician and therapy services. Led internal and agency teams to accomplish a 39.71% increase in website traffic, a 61% rise in leads, and a 58% growth in conversions through innovative digital marketing strategies. Developed and managed a robust social media content calendar, resulting in an 85% increase in LinkedIn followers, an 83% increase in Facebook reach, and a 32% rise in YouTube views. Conceptualized and executed impactful email and newsletter campaigns that achieved 30% higher open rates and 5% higher click-through rates compared to industry averages. Directed public relations efforts that achieved an impressive 88% success rate in raising social awareness. Designed and executed successful marketing launches and rebranding efforts for Spring Hills across four states, including Spring Hills Home Care Services, now known as Bedrock at Home, with offices in six states, Renaissance Home Health Care in New York, Poet’s Walk Memory Care Communities with eight locations across four states, and two Luxury Senior Living launches - Spring Hills Cherry Hill and Spring Hills Livingston. Pioneered a sales enablement system for assisted living, post-acute care, and home care services, streamlining operations and significantly boosting results. Spearheaded initiatives that garnered nine GDUSA Awards.