awayday Executive and Leadership Team

June, 2026

Leadership Overview

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

Driven by a commitment to fostering connection, awayday designs transformative group travel experiences that blend adventure, relaxation, and meaningful interaction, solidifying its market presence through expertly coordinated retreats and team-building journeys.

Leadership Roles at awayday

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

    Jakob Dwyer, the Chief Executive Officer at awayday, directs the overarching corporate strategy and vision, ensuring the company's mission to foster connection through curated group travel experiences remains paramount. Dwyer's leadership guides the organization's expansion into new markets and the development of innovative retreat offerings that combine adventure, relaxation, and team-building. Overseeing all major strategic initiatives, Dwyer ensures alignment across departments, driving the company's growth and market positioning within the hospitality and travel sector. This executive role involves cultivating key partnerships and stakeholder relationships, essential for maintaining awayday's reputation for delivering memorable and meaningful group getaways. The Chief Executive Officer's focus extends to championing the company's unique approach to simplifying complex group logistics, allowing participants to fully engage with the experience. By setting the strategic direction, Jakob Dwyer ensures awayday consistently delivers exceptional value and fosters genuine connection among travelers.
    Jakob Dwyer

    David Reed - Chief Financial Officer

    David Reed, the Chief Financial Officer at awayday, manages the company's financial health and strategic resource allocation, supporting the delivery of unique travel and team-building experiences. Reed oversees all financial operations, including budgeting, forecasting, and financial planning, ensuring the fiscal stability necessary for awayday's continued growth and innovation in the group travel market. This executive role is vital in assessing investment opportunities and managing financial risks associated with expanding the company's offerings in corporate retreats and social group getaways. By providing critical financial insights, the Chief Financial Officer enables informed decision-making across all departments, from marketing and sales to operations and product development. David Reed's financial stewardship ensures that awayday can continue to invest in creating carefully curated experiences that combine adventure, relaxation, and connection. The Chief Financial Officer's strategic financial management underpins the company's ability to deliver exceptional value and maintain its competitive edge.

    Matthew Loney - Chief Operating Officer

    Matthew Loney, the Chief Operating Officer at awayday, executes the operational framework that supports the company's mission of creating seamless group travel experiences. Loney oversees the comprehensive planning and coordination services, managing all aspects of trip execution from destination selection and accommodation booking to activity planning and transportation arrangements. This role is critical in ensuring the logistical efficiency and quality of every corporate retreat and team-building event organized by awayday. By optimizing vendor relationships and on-site logistics, the Chief Operating Officer guarantees that clients receive end-to-end support, allowing participants to focus on connection and engagement. Matthew Loney's operational oversight extends to refining processes that simplify the complexities of multi-person trips, thereby enhancing the overall client and participant satisfaction. The Chief Operating Officer drives operational excellence, ensuring awayday's commitment to delivering memorable and meaningful shared experiences through travel is consistently met.

    Charles Cannella - President of Resort Rentals

    Charles Cannella, the President of Resort Rentals at awayday, spearheads the strategic development and management of the company's resort rental portfolio, a key component of its group travel and retreat offerings. Cannella focuses on curating a selection of properties that align with awayday's mission to bring people together in memorable and meaningful ways, ensuring each location supports adventure, relaxation, and connection. This leadership position involves cultivating strong relationships with property owners and managers to secure exclusive access and favorable terms for group bookings. The President of Resort Rentals plays a crucial role in integrating these accommodations seamlessly into the comprehensive trip planning and coordination services awayday provides. Charles Cannella's expertise in the hospitality sector ensures that the resort rental experiences enhance the overall value proposition for corporate teams and social groups seeking unique getaway experiences. By optimizing the resort rental division, Cannella directly contributes to awayday's ability to deliver customized and high-quality group travel solutions.

    William Sangster - Regional President, Brand

    William Sangster, the Regional President, Brand at awayday, drives the strategic positioning and brand narrative across key geographic markets, amplifying the company's expertise in organizing group trips and team-building experiences. Sangster oversees brand development initiatives, ensuring awayday's commitment to creating memorable and meaningful connections through travel resonates with target audiences in North America and beyond. This executive role involves shaping marketing strategies and public relations efforts that highlight the company's comprehensive planning services, from destination selection to on-site logistics. By fostering a strong brand identity, William Sangster supports awayday's objective of simplifying complex group travel and allowing participants to focus on the experience itself. The Regional President, Brand works to enhance awayday's reputation as a partner for organizations and groups seeking expertly curated adventures and retreats. Sangster's leadership ensures the brand effectively communicates its value in combining adventure, relaxation, and genuine connection.

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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, President of Resort Rentals, Regional President, Brand.