Summary
Overview
Work History
Education
Skills
Accomplishments
Contact Information
Languages
Timeline
SalesManager
Dean Riddle

Dean Riddle

Hospitality, Operations & Business Leader
Lakewood Ranch,FL

Summary

Bilingual hospitality, operations, and business executive with 20+ years of leadership across hotels, partnership-owned companies, property management, automotive sales, consulting, and professional education in the United States and Costa Rica. Proven record of improving occupancy, revenue, guest satisfaction, financial controls, and team performance while managing multiple properties and concurrent business operations.

Overview

27
27
years of professional experience
4
4
years of post-secondary education

Work History

Founder / Program Director

Riddle Tax and Business Academy
Florida (Remote)
01.2026 - Current

• Develop and lead accessible Spanish-language training for ethical, service-oriented tax preparers, including tax fundamentals, basic accounting, software workflows, and professional development.
• Direct curriculum, marketing, student intake, virtual delivery, and TAOS operating systems for workshops, professional courses, specializations, mentorship, and certification pathways.

Independent Consultant

Dean Riddle Services
Florida
09.2023 - Current

• Advise hospitality and service businesses on operations, staffing, customer experience, financial organization, and profitability.
• Prepare individual and small-business tax returns and provide bilingual administrative support for immigration form preparation.
• Help business owners improve workflows, strengthen client service, and implement practical growth and marketing strategies.

General Manager - Multi-Property Portfolio

RiverBrook Equities
New York & Pennsylvania
03.2018 - 08.2023
  • • Selected properties managed include La Quinta Inn & Suites locations in Long Island City, Atlantic Avenue, and Rockaway Beach; Fairfield Inn & Suites by Marriott in Lancaster, PA; and The 2270.
    • Directed hotel operations, staffing, training, scheduling, budgeting, expense controls, vendors, facilities, and contract negotiations across properties managed sequentially and sometimes simultaneously under individual ownership LLCs.
    • Exceeded benchmark occupancy goals by at least 10% in multiple months and used STAR Report and competitive-set data to guide decisions.
    • Earned Wyndham Best of the Best recognition for two consecutive years and surpassed brand standards for guest satisfaction and NSP performance.
    • Expanded the customer base by 20% and secured two lodging contracts with New York City.

Sales Assistant Manager

Major World Chevrolet
New York, NY
05.2015 - 01.2018
  • Resolved customer issues or concerns quickly to close deals and boost client satisfaction.
  • Maintained ethical and positive working environment to reduce turnover and promote high retention rates.
  • Attended industry shows, conventions, and other meetings with primary mission of expanding market opportunities.
  • Met with clients, delivering presentations, and educating on product and service features and offerings.
  • Trained newly hired sales team in upselling techniques and educated staff on strategies for handling difficult customers and challenging situations.
  • Submitted reports to senior management to aid in business decision-making and planning.
  • Managed over 50 customer calls each day.

Sales & Leasing Consultant

Major World Chevrolet
New York, NY
04.2013 - 05.2015
  • Used consultative sales techniques to understand customer needs and recommend relevant products and services.
  • Achieving sales quota consistently for several months, exceeding it by at least 25%
  • Provided sales and customer service assistance to walk-in traffic
  • Responded to telephone and in-person requests for information.
  • Followed up with existing customers to provide additional support and address concerns.
  • Achieved top performance by strategically adapting to rapidly changing, competitive environment.
  • Stayed knowledgeable on latest Chevrolet developments and innovations and technological advancements through continuous training.

Property Manager

Costa Rica Advisors SA
Jaco Beach, Costa Rica.
01.2009 - 01.2013
  • Handled tenant complaints promptly and appropriately, calling in repairmen, and other support services.
  • Completed final move-out walk-throughs with tenants to identify required repairs.
  • Followed up on delinquent tenants and coordinated collection procedures.
  • Maintained original leases and renewal documents in digital and hardcopy format for property management office.
  • Maintained operational facilities attractive to potential tenants by organizing regular maintenance, major repairs, and capital improvement projects.
  • Acquire 2 new accounts per month.
  • Monitored progress of construction and maintenance projects and notified appropriate individuals of project updates, delays, and schedule changes.
  • Monitored tenant behavior and implemented corrective action to maintain order in assigned properties.
  • Coordinated with janitorial and engineering staff on maintenance and upkeep.
  • Kept properties in compliance with local, state and federal regulations.
  • Collected and maintained careful records of rental payments and payment dates.
  • Communicated effectively with owners, residents, and on-site associates.

Operations Manager / Partner

Costa Rica Rent All S.A.
Jaco Beach, Costa Rica
01.2004 - 12.2012

• Managed operations for a portfolio of more than 78 properties, including owner relations, tenant and guest service, maintenance, housekeeping, leasing, and collections.
• Supervised field and office teams, coordinated repairs and capital projects, negotiated service contracts, and maintained operational and financial records.
• Expanded the management portfolio through relationship-based business development and dependable service to property owners.
• Led the operation through the Costa Rican real-estate downturn until the company closed during the market crisis.

Co-Founder / Operations & Finance Executive

Stay in Costa Rica S.A.
Jaco Beach, Costa Rica
01.2000 - 12.2004
  • • Co-founded and helped lead a property-management business serving more than 100 tenants across 114 vacation and residential property units in a major tourism market.
    • Oversaw operations, financial administration, payroll support, contracts, client reporting, team hiring, and service delivery.
    • Built scalable processes for property care, reservations, customer communication, and coordination of maintenance and housekeeping teams.

Education

Manager Advanced Training - Hotel Management

Wyndham University
New Jersey
06.2019

Certificate of Fitness - Fire And Life Safety Director (FLSD)

New York City Fire Department
New York, NY
01.2019

Bachiller En Derecho (Bachelor's Degree in Law) - Law

Escuela Libre De Derecho
San Jose, Costa Rica
01.1992 - 12.1995

Skills

  • Multi-Property Hotel Operations
    Revenue and Occupancy Growth
    Budgeting and P&L Oversight
    Team Leadership and Staff Development
    Guest Satisfaction
    Sales and Business Development
    Contract Negotiation
    Facilities and Vendor Management
    Process Improvement
    Bilingual English-Spanish Client Service

Accomplishments

  • Implemented marketing strategies which resulted in 20% growth of customer base.
  • Recognized Best of the Best by Wyndham, 2 years in a row.

Contact Information

Cell: 646-852-8961
Dean Riddle Services: 929-383-3633
Personal email: dean1riddle@gmail.com
Business email: dean@deanriddleservices.com

Languages

Spanish
Native or Bilingual

Timeline

Founder / Program Director

Riddle Tax and Business Academy
01.2026 - Current

Independent Consultant

Dean Riddle Services
09.2023 - Current

General Manager - Multi-Property Portfolio

RiverBrook Equities
03.2018 - 08.2023

Sales Assistant Manager

Major World Chevrolet
05.2015 - 01.2018

Sales & Leasing Consultant

Major World Chevrolet
04.2013 - 05.2015

Property Manager

Costa Rica Advisors SA
01.2009 - 01.2013

Operations Manager / Partner

Costa Rica Rent All S.A.
01.2004 - 12.2012

Co-Founder / Operations & Finance Executive

Stay in Costa Rica S.A.
01.2000 - 12.2004

Bachiller En Derecho (Bachelor's Degree in Law) - Law

Escuela Libre De Derecho
01.1992 - 12.1995

Manager Advanced Training - Hotel Management

Wyndham University

Certificate of Fitness - Fire And Life Safety Director (FLSD)

New York City Fire Department
Dean RiddleHospitality, Operations & Business Leader