Ryan Winter Redefines Business Leadership with Scalable Systems, Sales Brilliance, and Visionary Marketing Strategy

Chief Operating Officer Ryan Winter helps businesses scale through smart systems, sales strategy, and team leadership—delivering growth and lasting results.

SAINT JOHNS, FL, UNITED STATES, April 15, 2025 /EINPresswire.com/ -- In the evolving landscape of executive leadership, few figures are as versatile and visionary as Ryan Winter. A powerhouse in operations, sales strategy, and marketing leadership, Winter is setting a new standard for what it means to be a modern-day Fractional Chief Operating Officer. Based in St. Johns, Florida, he’s quietly becoming the secret weapon behind some of the most profitable business transformations in recent years.

As the founder and principal of Pro Business Advice, Winter has helped multiple organizations—from SaaS companies and dealerships to professional service firms and nonprofits—move from bottlenecks to breakthroughs. His approach? Systems that scale, processes that perform, and people that thrive.

“I’m not just here to help a business function better,” says Winter. “I’m here to help it become bulletproof.”

The Fractional COO Behind Six-Figure Growth Stories
At Pro Business Advice, Ryan has taken a business from zero to over $170,000 in annual revenue in the first year—bootstrapped, productized, and built entirely through his own strategic guidance. But he’s not stopping there.

He developed a proprietary consulting structure based on hourly deliverables, allowing for both scalability and training of additional consultants. Today, Ryan oversees a team of 18 independent consultants, all aligned around clear KPIs, weekly accountability rhythms, and tailored training systems hosted via Waybook.

He also leads a high-level Cohort Program for Fractional Integrators and COOs, facilitating weekly mastermind calls, joint marketing efforts, and structured peer support designed to elevate the entire industry.

Through his work, Ryan has helped companies:

Hit the highest revenue growth in 30+ years

Move from contractor-heavy teams to 100% full-time staff for better accountability

Create new leadership roles that directly increased profit margins

Implement automated CRM systems and SOPs that cut workload by 40%

Retain clients for over a year in high-churn industries

“Most clients stay on for many months—some over a year,” says Winter. “That tells me we’re not just delivering value. We’re changing how they think about their business.”

Real COO Results, Real Fast
Before launching Pro Business Advice, Ryan served as COO and EOS Integrator for EverLogic Software, where his leadership led to the most profitable year in the company’s 13-year history. By rebuilding the sales funnel, implementing HubSpot CRM, launching Google Ads, and introducing a 20% price increase with minimal churn, he gave EverLogic a modern sales and marketing engine that actually worked.

He structured and managed a 20-person team across sales, marketing, and leadership—complete with weekly scorecards, KPIs, and department check-ins. He didn’t just manage operations; he activated them.

Ryan also introduced structured team training programs, performance dashboards, and even a revamped commission plan—resulting in a measurable surge in both team morale and revenue output.

His leadership at EverLogic wasn’t just tactical—it was cultural. He introduced Level 10 leadership meetings (from the Entrepreneurial Operating System playbook), reorganized department heads, and ran high-conversion video marketing campaigns to reestablish the brand's digital credibility.

“When you give people clarity, structure, and autonomy, amazing things happen,” he says.

A Sales Leader Who Builds Pipelines and People
Unlike many operational leaders, Ryan brings high-level sales leadership to every table he sits at. During his time as a Senior Account Manager at Advantage B2B Consulting + Marketing, he led strategic marketing initiatives that boosted client retention and built out the firm’s CRM-driven approach to lead generation.

He introduced buyer persona development, launched full-scale marketing automation campaigns, and helped grow a 15,000-contact email list that became the backbone of the firm’s digital outreach. He also collaborated with creative contractors, led content strategy, and refined forecasting models—all while building deep client relationships that translated to repeat business and long-term success.

Earlier in his career, as a top-producing real estate broker in Jacksonville, Ryan closed over $3 million in transactions annually while launching Giving House, a charitable initiative donating 25% of his commissions to nonprofits selected by his clients. That effort alone earned media attention and helped reinforce his personal brand as a values-first entrepreneur.

“Great businesses do more than generate profit—they create impact,” says Winter. “Giving House was my way of walking that out.”

Operational Leadership Rooted in Purpose
Ryan’s leadership philosophy was forged not only in boardrooms, but also in the villages of Tanzania, where he served as Executive Director & COO for the nonprofit Water for All Nations. There, he led fundraising campaigns that secured $30,000+ in six months, piloted clean water systems while living in East Africa, and built a board of directors that helped scale the organization’s mission and visibility.

His nonprofit leadership also included building out donor management systems, launching a successful gala with over 200 attendees, and securing recurring donations to sustain the organization’s programs. He applied business principles—KPI tracking, CRM systems, StoryBrand messaging—to elevate a mission-driven cause.

“Business is just organized problem solving. Whether you’re selling software or drilling wells, the principles of leadership and efficiency apply,” Ryan reflects.

Certifications & Credentials
Ryan holds a Bachelor of Science in Advertising Communications from the University of North Florida and an Associate of Arts from Florida State College. He’s certified in:

EOS (Entrepreneurial Operating System) Integration

HubSpot CRM

SharpSpring CRM

His technical stack includes: HubSpot, GoHighLevel, SharpSpring, Google Ads, WordPress, Waybook, QGiv, Mailchimp, Trello, Asana, Notion, Zapier, Google Analytics, QuickBooks, Slack, Zoom, and more.

Availability
Ryan Winter is currently accepting new Fractional COO engagements, sales strategy projects, and full-time executive leadership opportunities. He brings with him not just an impressive resume—but an uncommon ability to unite people, process, and purpose into business systems that win.

“I want to work with organizations that are hungry for change and ready to scale—not just in revenue, but in legacy,” says Winter. “That’s the work I’m built for.”

Ryan Winter
Ryan Winter LLC, DBA Pro Business Advice
+1 904-735-8994
ryan@probusinessadvice.com