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Company History

Incorporated Icon

Incorporated 1968

SITE Crystal Awards Icon

Winner of five 1st Place SITE Crystal Awards.

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Creator of the first Individual Incentive Travel Program in history.

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Originator of 39 landmark group events. (Many like the helicopter cocktail party atop Mendenhall Glacier still operate.)

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Owner of The Journeymasters Building, four story edifice in downtown Salem, MA.

Our Team

  • 1 of 7 founders and 1st full term president of SITE (The Society of Incentive Travel Executives)
  • 1st president of The SITE Foundation, the independent research arm of the society
  • Earned the society’s CITE designation 1985. (Certified Incentive Travel Executive)
  • Recipient SITE’s Lifetime Achievement Award 2001. (Four awarded – to date – in the history of the society)
  • Named “honorary citizen” of Venezuela 1969
  • Named “Tourist Personality of the Year” for Rio de Janeiro. 1973
  • Served 7 years on the IT&ME (now The Motivation Show), Advisory council
  • Served 10 years on the Las Vegas Corporate & Incentive Travel Council
Bob Guerriero

Bob Guerriero

President & Executive Director

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  • 27 years a Journeymaster
  • Hired from Salem’s historic Hawthorne Hotel where she served as Rooms Division Manager
  • Oversees the flawless execution of Going Places higher & higher and Above & Beyond™
  • Negotiates final costs for much of the individual incentive programs. Negotiates hotel & ground contracts for group trips
  • Creates group trip cost sheets & proposals
  • Trip Director for many international and Caribbean incentive trips
  • Sales representative for many Journeymasters' clients
  • Supervises human resources
  • Hired every member of the Redeem Team
Kris Sierra

Kris Sierra

Vice President Administration

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  • 31 years a Journeymaster
  • 34 years in the travel industry
  • Co-designer and point person on the in-progress procedures for group trips
  • Ultimate editor of all printed pieces and internet sites produced by the company
  • Most importantly, Christine is in charge of group clients & guests; their comfort level and satisfaction
  • Trip Director for many successful groups in the United States, Central America, Asia, Carribean, Europe, and Africa
  • Passionate about Bob, the beach, and Bruce
Christine Guerriero

Christine Guerriero

Vice President Travel Management

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  • 37 years a Journeymaster
  • Created and oversees the information system that tracks the myriad elements of a group trip; manifest, rooming lists, room counts, guest counts, accounting controls
  • Created and oversees the information system of both individual travel programs (Going Places and Above & Beyond™), that tracks activities of the guest with the redeem team, spoken or written. With our system any journeymaster can answer any question any guest may have since each guest conversation is noted in the information packet of the guest
Keith Guerriero

Keith Guerriero

Vice President Data Management

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  • 20 years a Journeymaster
  • 36 years of travel industry experience
  • Manages the Group Incentive Department
  • Creates group trip proposals to deliver unforgettable journeys
  • Negotiates Air, Hotel, and Ground contracts
  • Manages the air travel for guests traveling with groups
  • Trip Director for many successful groups to include Alaska, Italy & Puerto Rico to name a few
  • While not working, Nancy enjoys playing tennis, rooting on her New England Sports teams and, of course, traveling with her husband and two sons!
Nancy Coletti

Nancy Coletti

Manager Travel Operations

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  • 20 years a Journeymaster - in Salem, the Bay Area of California, and now western New York
  • Started in Salem in 1997 as Office Assistant and eventually became Project Supervisor, supported all aspects of the Journeymasters company from answering phones to booking trips for the Redeem Team, editing web content and acting as Trip Director in Hong Kong, Jamaica, and Mexico
  • Creates printed materials, promotional items, email marketing, and client proposals for Group Trips as well as our Individual programs
Rachel Richards

Rachel Richards

Project Supervisor

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  • Rachel is brand new to The Journeymasters family
  • Rachel helps to design and create the websites and printed catalogues
  • Creates and designs promotional materials for print and digital media
  • Rachel has become the unofficial photographer at The Journeymasters
  • With a background in sales and visual merchandising, Rachel fosters a creative direction aligned with The Journeymasters' brand positioning
  • Prepares final print and web ready art to be used on Journeymasters media
  • Rachel assists and supports all of the departments at The Journeymasters
Rachel Leibowitz

Rachel Leibowitz

Project Coordinator

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  • 2 years a Journeymaster
  • 17 years of experience in the accounting & financials industry
  • Manages the accuracy of accounting and financial details
  • Reconciliation of all company purchases
  • Creation and reconciliation of all company billings
Jenn Maggs

Jenn Maggs

Financial Administrator

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  • 10 years a journeymaster
  • A vital support member of The Journeymaster’s team
  • He insures the environment is conducive to us accomplishing our mission without distractions due to building maintenance
  • And supervises the relationship with the buildings other tenants
Dino Dicienzo

Dino Dicienzo

Building Manager

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The Redeem Team

The Journeymasters who are the vital heart of our Trips-for-Two programs.

These are the people who make our concierge service operate so flawlessly. 96% of the winners responding to our post-trip survey that we call A Moment of Your Time (MOYT) told us their journey exceeded or met their expectations!

Book your award trip now so you can join our 96% happiness rate!

  • 5 years a Journeymaster
  • 10 years in the travel industry
  • Oversees the day-to-day operations of the remarkable Redeem Team
  • Responsible for negotiating hotel contracts
  • Responsible for on-going promotional reminders to unredeemed award winners
John MacDearmid

John MacDearmid

Manager of the Redeem Team

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  • Over 15 years a Journeymaster
  • 32 years a travel agent
  • Provides Concierge Service to individual trip winners
  • Disney World expert
  • Oversees all airline ticket reporting
  • Supports the Redeem Team
Rita Cassidy

Rita Cassidy

Senior Travel Specialist

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  • 2 years a Journeymaster
  • 7 years of travel experience
  • Valued member of the Redeem Team
  • Assists with ground operation details on group trips
  • Printing and cutting expert
  • Strong legs from going up and down stairs multiple times a day
Paul Metler

Paul Metler

Travel Consultant

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  • Newest Redeem Team Member since June 2016
  • Over 20 years of experience in the travel industry
  • Redeems travel awards for winners by researching destinations
  • Makes hotel, air, and cruise reservations
Stefanie Flammia

Stefanie Flammia

Travel Consultant

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