awayday Executive and Leadership Team

May, 2026

Leadership Overview

Awayday has 5 executives leading key functions including strategy, finance, operations, brand, and resort rentals.

Driven by a commitment to connection, awayday specializes in crafting group travel experiences that foster memorable and meaningful interactions, combining adventure, relaxation, and team cohesion for corporate and social groups alike.

Leadership Roles at awayday

  • Chief Executive Officer - Jakob Dwyer
  • Chief Financial Officer - David Reed
  • Chief Operating Officer - Matthew Loney
  • Regional President, Brand - William Sangster
  • President of Resort Rentals - Charles Cannella
  • Jakob Dwyer - Chief Executive Officer

    Jakob Dwyer, the Chief Executive Officer at awayday, directs the overarching strategy and vision for the company's group travel and team-building experiences. Dwyer guides the organization's focus on creating carefully curated journeys that blend adventure, relaxation, and genuine connection for corporate teams and social groups. Overseeing all major strategic initiatives, Dwyer ensures the company's offerings align with its mission to bring people together in memorable ways. This leadership role involves setting the direction for product development, market expansion, and client engagement strategies. By fostering a culture of innovation and client-centricity, Jakob Dwyer drives the company's growth and its reputation as a premier organizer of group travel. Dwyer's strategic direction ensures that awayday consistently delivers unique getaway experiences that meet specific client objectives, whether for team building, celebration, or adventure.
    Jakob Dwyer

    David Reed - Chief Financial Officer

    David Reed, the Chief Financial Officer at awayday, manages all financial operations and fiscal strategy for the travel and experience company. Reed oversees budgeting, financial planning, and resource allocation to support the organization's mission of creating group trips and corporate retreats. This role involves ensuring the financial health and sustainability of awayday's comprehensive trip planning and coordination services. By analyzing financial performance and identifying opportunities for fiscal optimization, David Reed contributes to the company's ability to offer customized experiences within client budgets. Reed's oversight extends to managing investments, financial reporting, and risk management, thereby safeguarding the company's assets and supporting its expansion into new markets. The financial guidance provided by the Chief Financial Officer is critical for enabling awayday to handle the complexities of multi-person trips and deliver exceptional value.

    Matthew Loney - Chief Operating Officer

    Matthew Loney, the Chief Operating Officer at awayday, directs the operational execution of all group trips, corporate retreats, and team-building experiences. Loney oversees the comprehensive planning and coordination services, ensuring seamless execution from destination selection to on-site logistics. This leadership position involves managing vendor relationships, optimizing transportation arrangements, and streamlining accommodation bookings to facilitate memorable and meaningful travel experiences. By focusing on efficient operational processes, Matthew Loney ensures that awayday can handle the complexities of multi-person trips, allowing participants to concentrate on connection and enjoyment. Loney's operational expertise is vital in delivering end-to-end support, from initial planning through trip execution and follow-up, reinforcing awayday's commitment to simplifying group travel logistics and fostering genuine collaboration among participants.

    William Sangster - Regional President, Brand

    William Sangster, the Regional President, Brand at awayday, leads the strategic development and management of the company's brand identity and market presence across key regions. Sangster focuses on enhancing awayday's reputation for organizing group trips, corporate retreats, and team-building experiences that emphasize connection and memorable moments. This role involves shaping the brand narrative and ensuring consistent messaging that highlights the company's specialization in curated travel that combines adventure, relaxation, and collaboration. By overseeing brand initiatives, William Sangster supports the company's efforts to attract and retain corporate clients and social groups seeking unique getaway experiences. Sangster's leadership ensures that the awayday brand resonates with its target audience, underscoring the value of expertly planned and coordinated group travel that fosters genuine interaction and lasting memories.

    Charles Cannella - President of Resort Rentals

    Charles Cannella, the President of Resort Rentals at awayday, spearheads the strategic direction and operational oversight of the company's resort rental division. Cannella focuses on curating and managing a portfolio of properties that serve as ideal venues for group trips, corporate retreats, and team-building experiences. This leadership role involves ensuring that resort offerings align with awayday's mission to create memorable and meaningful connections among participants. By managing relationships with resort partners and overseeing the quality of accommodations, Charles Cannella ensures that clients receive exceptional value and seamless logistical support. Cannella's expertise is critical in designing customized experiences that balance adventure, relaxation, and group interaction, reinforcing awayday's position as a partner for organizations seeking to foster collaboration and shared moments through travel.

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    Frequently Asked Questions Regarding awayday Top Executives and Leadership Team

    Who leads awayday?
    awayday is led by Jakob Dwyer (Chief Executive Officer), along with executives such as David Reed (Chief Financial Officer) and Matthew Loney (Chief Operating Officer).
    Who is part of awayday’s executive team?
    The executive team of awayday includes leaders such as Jakob Dwyer (Chief Executive Officer), David Reed (Chief Financial Officer), Matthew Loney (Chief Operating Officer) and other senior executives.
    How many executives does awayday have?
    awayday has 5 executives leading key business areas.
    What roles are included in awayday’s leadership team?
    The leadership team of awayday includes roles such as Chief Executive Officer, Chief Financial Officer, Chief Operating Officer, Regional President, Brand, President of Resort Rentals.