AREA DIRECTOR OF GROUP SALES - MAUI

About Our Company

Springboard Hospitality is a premier third-party hotel management company with a 30+ year legacy of transforming lifestyle hotels from the islands of Hawaii to the tip of Florida.

Our team is a vibrant community of innovators, storytellers, and experience-makers who bring each property to life. At Springboard, we go Above & Beyond to create meaningful moments for our guests, elevate our team members, and inspire authentic connections within our communities.

Our diverse portfolio features distinctive hotels that reflect their local essence. We empower our teams through intentional culture, growth opportunities, and a shared vision to redefine hospitality. From career development to travel perks, Springboard is proud to support a thriving workplace where our people stay, grow, and lead the way.

www.springboardhospitality.com

Primary Mission

As the Area Director of Group Sales – Maui, you will lead the group sales strategy and execution across our Maui properties. This multi-property role is responsible for driving group business performance, cultivating key relationships, and aligning with hotel leadership to exceed revenue and customer satisfaction goals.

You’ll be a strategic partner and hands-on leader, guiding hotel-based sales teams while representing Maui properties at a regional level. Your focus will be on maximizing group room revenue, nurturing high-value accounts, and bringing creative, localized strategies to life.

Scope of Work + Team

• Oversees group sales efforts across designated Maui hotels

• Collaborates closely with on-property GMs and Sales Leaders

• Reports directly to the Corporate Director of Sales

• Interfaces with the Special Events and Catering team where applicable

• Based in Maui, Hawaii (travel between properties as needed)

Responsibilities

• Lead and implement group sales strategies to achieve and exceed revenue targets across Maui hotels.

• Proactively solicit, negotiate, and book new and repeat group business through sales calls, site visits, networking, trade shows, and digital outreach.

• Develop and manage key accounts and partnerships within corporate, association, and travel segments.

• Work in partnership with hotel leadership and the Corporate Sales team to ensure strategic alignment and seamless execution of group business.

• Collaborate with the Catering and Events teams where applicable to deliver cohesive group experiences and drive ancillary revenue.

• Analyze market trends, competition, and performance data to guide pricing and positioning decisions.

• Prepare annual group sales budgets, forecasts, and performance reports for assigned properties.

• Provide leadership, training, and mentorship to on-property sales teams; build high-performance, guest-focused sales culture.

• Represent Maui properties in regional sales meetings, brand activations, and industry events.

• Actively promote Springboard Hospitality’s culture and values, leading with collaboration, integrity, and innovation.

Qualifications

• Minimum 5 years of sales leadership experience, preferably in multi-property or resort environments.

• Proven track record of exceeding group revenue goals and building strong client relationships.

• Deep knowledge of group sales processes, B2B channels, and hospitality CRM systems.

• Strong organizational and communication skills, with the ability to lead cross-functional teams.

• Knowledge of the Hawaii travel and hospitality market preferred.

• Ability to travel between Maui properties and occasionally to Oahu or the mainland for regional meetings or conferences.

EXPERIENCE:

• Prior Experience:
  • 6+ years as top sales leader position in a hotel/hospitality environment of comparable scale to OLS Hotels & Resorts or six years of employment in a related position with this company or other companies.
  • Previous sales and marketing leadership responsibility overseeing all related functions for an upscale or boutique/luxury property of comparable scale to OLS Hotels & Resorts (four diamond level or higher).
  • Knowledge of travel trade industry, group markets and leisure segment including key contacts that would serve to source business for the property and that align with the profile and prestige positioning of OLS Hotels & Resorts.
• IT Expertise:
  • Advanced knowledge of computer software (including Microsoft Office, outlook) and web analytics tools is preferred.

• Education:
  • A four-year college degree or equivalent education/experience
• Subject Expertise:
  • Participate in trade shows and community and professional organizations to maintain high visibility and the achievement of sales and revenue goals
  • Perform special projects and other responsibilities as assigned. 
  • Participate in hotel committees, MOD program and task force assignments.
  • Assist the Front Office Manager in all areas requested and act in his/her place during his/her absence
  • Demonstrate a working knowledge of all property safety and security procedures as required maintaining a secure and safe environment for employees as well as guests.
  • Report any unusual occurrences and/or request to Supervisor.
  • Read and abide by all the regulations and rules of conduct stated in the Associate Handbook.
  • Must be service oriented with excellent customer service and sales skills
  • Must be able to effectively communicate to guests, management, and coworkers and read, write and understand the English language
  • Must be energetic and outgoing
  • Must possess excellent interpersonal and organizational skills
  • Must be able to follow directions with attention to detail, speed and accuracy
  • Must be a team player with the ability to work under minimal supervision
  • Must be able to multi-task in a fast-paced work environment
  • Must be able to understand and work with basic financial information and solve basic arithmetic problems
  • Must be able to type 45 wpm and have the ability to input data and access information on the computer
  • Must have proficient working knowledge of Microsoft Office, Opera; preferred.
  • Must be able to exercise confidentiality and discretion.

OTHER EXPECTATIONS:

• Abide by payroll policies, procedures and rules of conduct as stated in the Springboard Hospitality Associate Handbook.
• Demonstrate a working knowledge of all company safety and security procedures.
• Travel required: As needed for hotel familiarization, content creation shoots and to meet with colleagues.
• Hours Required: Must primarily work during Springboard Hospitality business hours, Monday - Friday 8am - 5pm (PST), while understanding that the hotel business functions 24/7 and some weekend or holiday work may occasionally be required.

Benefits:

Springboard Hospitality offers an empowered working environment that encourages collaboration and flexibility. We offer a superior benefits package to employees who work 20 hours/week or more that includes:

Full Time Benefits

• Competitive Base Salary
• PTO
• Medical, Dental, Vision, Life, Pet Insurance
• 401K
• Costco Membership
• Bereavement Leave
• Management Contract Referral Program
• Education Assistance

Additional Per Position

• Employee Rates at all of Springboard Hospitality’s 35+ Hotels
• Monthly Cell Phone Stipend
• Dry Cleaning Services
• Hotel Level Executive Bonus Program
• Retention Bonuses
• Lead Share Program
• Associate of the Month/Quarter & Company-wide Associate of the Year Programs
• Associate Referral Bonus Program

Springboard Hospitality Core Values:

• CONNECTED. We are plugged into people, technology and the cutting edge of culture.
• INDEPENDENT. We are free-thinkers who embrace diversity and advocate for innovation.
• COLLABORATIVE. We are collaborative and believe that the best solutions are found by working hand-in-hand.
• PERSONALIZED. We are devoted to authentic human connection, personalizing our approach to the guests and owners that we serve.
• DYNAMIC. We are analytic thought leaders who harness the power of data to maximize return on investment.

OLS Hotels & Resorts LLC dba Springboard Hospitality (Springboard) is an equal opportunity employer.  Springboard provides equal employment opportunity for all associates and prohibits discrimination based on race, color, sex (including pregnancy, childbirth, breastfeeding and medical conditions related to pregnancy, childbirth, or breastfeeding), gender, religious creed (including religious dress and grooming practices), marital status, domestic partner status, age, national origin or ancestry, physical or mental disability, medical condition, genetic information and characteristics, sexual orientation, gender identity or expression, military or veteran status, or any other basis protected under federal, state, or local laws.  Springboard also provides reasonable accommodations for qualified applicants and employees with disabilities or medical conditions in accordance with applicable laws.