Executive leadership. Operational execution. Government ready.
Guillory Advisory Group is led by Rickey Guillory, an operations and business consulting executive with more than 25 years of leadership experience driving organizational growth, operational performance, and scalable business execution across hospitality, retail, service, and regulated industries.
Throughout his career, Rickey has overseen more than $700 million in transaction volume while leading sales organizations, operational initiatives, workforce development, and business modernization efforts. His experience blends executive-level strategic leadership with hands-on field execution, helping organizations improve efficiency, strengthen accountability, and scale operations effectively.
He holds a Master of Management degree from the University of Phoenix, bringing together formal business strategy, operational discipline, and real-world execution to support both commercial and government contracting initiatives.
The story
Rickey's career started on the floor at Bay Meadows, Golden Gate Fields, and the Northern California Fair Circuit, where he spent twenty years as a Sales Supervisor on track in the thoroughbred horse racing industry. He oversaw the cashing and selling of pari-mutuel wagering across the floor, which required him to be licensed by the California Horse Racing Board (CHRB). The role operated inside a heavily regulated environment and demanded precision under pressure: daily cash reconciliation, regulatory compliance, staff training, and live customer dispute resolution across high-volume race days.
Overlapping that run, he spent more than a decade with Sam Spear Enterprises as the backup on-air personality for Today at the Races on KTSF Channel 26 in San Francisco, while selling commercial airtime to local business owners. The 5:00 PM Bay Area broadcast reached a demographic of roughly 1.5 million viewers. Live television sharpened the communication; ad sales sharpened the operator conversation.
He transitioned to payments technology as one of the first field account executives in Northern California for an emerging POS and payments platform. Over eight years of continuous performance, he earned five successive promotions: Sales Trainer, Sales Director, Sales Mentor, and Regional Sales Manager, helping the organization scale through multiple Series funding rounds to a $5B valuation while advising operators on $700M+ in transacted volume.
Along the way, he built the company's first sales training function, authored an onboarding curriculum deployed nationwide across the field organization, and led high-performing teams in Northern and Central California. The work was grounded in Challenger fundamentals: teach the operator something new about their business, tailor the conversation, take control of the cycle.
The pattern across thousands of operator conversations was always the same: businesses overspending on processing, fighting disconnected systems, and making decisions on data they couldn't trust. The fix wasn't another vendor; it was a sharper operating model.
Guillory Advisory Group was founded to deliver that model directly: a consulting and payments strategy practice that pairs cost reduction with the operational rewiring that makes growth sustainable.
Outside of work, the same principles apply. Discipline. Long-haul thinking.
"The horse gets fed every day, regardless of the weather, and so do the clients."
A purposeful, choreographed approach.
We don't rely on transactional selling or surface-level relationships. Every engagement is built on insight, structured execution, and controlled conversations that drive real business outcomes.
By teaching clients something new about their business, tailoring solutions to their specific environment, and taking control of the decision process, we help organizations reduce cost, improve operations, and scale with confidence.
- 01
Teach
Surface a sharper view of the operation, the numbers, the gaps, and the leverage points the team hasn't seen yet.
- 02
Tailor
Shape the recommendation around your environment, your stack, your locations, and your team's capacity to execute.
- 03
Take control
Choreograph the decision process end to end so timelines hold, vendors stay accountable, and the outcome lands.
Our Approach to Operational Consulting.
Partnership Driven Consulting
We build long-term partnerships by improving operations, building scalable infrastructure, providing organizational support, and delivering measurable business outcomes.
Outcome Driven Consulting
Every recommendation is tied to operational performance, organizational efficiency, workforce alignment, infrastructure modernization, or measurable business improvement.
Executive Operational Experience
Built through decades of leadership experience supporting operational growth, workforce development, business modernization, and scalable execution across complex organizations.