awayday Executive and Leadership Team

October, 2026

Leadership Overview

awayday has 8 executives leading key functions including strategy, operations, financial management, and brand development.

Focused on fostering genuine human connection through curated travel, awayday delivers transformative group experiences that balance professional collaboration with leisure and adventure for corporate and social clients worldwide.

Leadership Roles at awayday

  • Chief Executive Officer - Jakob Dwyer
  • Chief Financial Officer - David Reed
  • Chief Operating Officer - Dan Yankley
  • Chief Operating Officer, Drove Organic & Inorganic Ebitda Growth For PE-Backed Portfolio Company - Matthew Loney
  • Regional President, Brand - William Sangster
  • President of Resort Rentals - Charles Cannella
  • President, Brand - Kristen Williams
  • President, Brand - Rj McClure
  • Jakob Dwyer - Chief Executive Officer

    Jakob Dwyer, the Chief Executive Officer at awayday, directs the overarching vision and strategic trajectory of the organization. By aligning corporate objectives with the evolving needs of group travel, the Chief Executive Officer ensures that every retreat fosters meaningful connection and collaboration. Dwyer maintains a focus on scaling the company's end-to-end planning services to meet the demands of diverse corporate and social clients. Through rigorous oversight of destination partnerships and vendor relationships, the Chief Executive Officer simplifies complex logistics for participants. Jakob Dwyer actively engages with the board to secure long-term growth while maintaining the high standards of service that define the brand. This leadership role involves constant evaluation of market trends to keep the company at the forefront of the hospitality industry. By prioritizing innovation in experience design, the Chief Executive Officer drives the company toward sustained excellence in the competitive travel sector.
    Jakob Dwyer

    David Reed - Chief Financial Officer

    David Reed, the Chief Financial Officer at awayday, governs the fiscal health and economic strategy of the enterprise. By managing capital allocation and budgeting processes, the Chief Financial Officer ensures that the company maintains the resources necessary to curate high-end travel experiences. Reed oversees financial reporting and risk management, providing the data-driven insights required for informed decision-making at the executive level. David Reed works closely with the leadership team to evaluate the profitability of various destination partnerships and service offerings. This role involves maintaining strong relationships with investors and financial stakeholders to support the company's expansion goals. By implementing robust financial controls, the Chief Financial Officer protects the organization's assets while enabling investment in new technology and service capabilities. Through careful analysis of revenue streams and cost structures, the Chief Financial Officer supports the long-term financial stability and growth of the entire business model.

    Dan Yankley - Chief Operating Officer

    Dan Yankley, the Chief Operating Officer at awayday, manages the internal infrastructure and logistical execution of all group travel programs. Overseeing the daily operations of the planning teams, the Chief Operating Officer ensures that every aspect of trip coordination, from accommodation booking to on-site activity management, functions with precision. Yankley focuses on optimizing internal workflows to reduce the stress typically associated with multi-person travel arrangements. By streamlining communication between vendors and clients, the Chief Operating Officer maintains the high quality of service expected by corporate partners. Dan Yankley monitors operational efficiency across all regional markets to ensure consistent delivery of the company's unique travel experiences. This role requires constant coordination with other C-suite leaders to align logistical capabilities with the broader strategic goals of the organization. Through meticulous attention to detail, the Chief Operating Officer guarantees that every retreat meets the specific objectives of the client.
    Dan Yankley

    Matthew Loney - Chief Operating Officer, Drove Organic & Inorganic Ebitda Growth For PE-Backed Portfolio Company

    Matthew Loney, the Chief Operating Officer, Drove Organic & Inorganic Ebitda Growth For PE-Backed Portfolio Company at awayday, focuses on driving scalable growth through strategic operational improvements. By identifying opportunities for both organic expansion and inorganic acquisitions, the Chief Operating Officer enhances the company's market position within the travel industry. Loney analyzes performance metrics to optimize the delivery of corporate retreats and team-building experiences. Matthew Loney collaborates with the finance department to ensure that operational scaling aligns with the company's broader economic targets. This leadership role involves refining the processes that support the company's end-to-end planning services, ensuring that growth does not compromise the quality of client experiences. By implementing rigorous performance standards, the Chief Operating Officer drives efficiency across all departments. Through a focus on sustainable growth, the Chief Operating Officer ensures that the company remains a leader in providing memorable and meaningful group travel solutions.

    William Sangster - Regional President, Brand

    William Sangster, the Regional President, Brand at awayday, directs the market presence and brand identity across key operational territories. By overseeing regional initiatives, the Regional President, Brand ensures that the company's reputation for excellence remains consistent in every market. Sangster develops localized strategies that resonate with corporate clients seeking offsite meetings and team retreats. William Sangster manages the relationships with regional vendors and destination partners to maintain the high standards of the company's curated experiences. This role involves coordinating with the broader leadership team to ensure that regional activities align with the global brand mission. By monitoring local market trends and client feedback, the Regional President, Brand adapts service offerings to meet specific regional needs. Through active engagement with local organizations, the Regional President, Brand drives brand awareness and strengthens the company's position as a premier partner for group travel and team-building experiences.

    Charles Cannella - President of Resort Rentals

    Charles Cannella, the President of Resort Rentals at awayday, manages the portfolio of accommodations and lodging partnerships essential to the company's travel experiences. By securing high-quality properties that facilitate connection and relaxation, the President of Resort Rentals ensures that every group retreat takes place in an environment conducive to the company's mission. Cannella oversees the negotiation of contracts with resort operators to guarantee favorable terms and exclusive access for clients. Charles Cannella works with the planning teams to match specific group needs with the most appropriate lodging options, whether for corporate retreats or social getaways. This role involves constant evaluation of property standards and guest satisfaction metrics to maintain the company's reputation for quality. By optimizing the accommodation supply chain, the President of Resort Rentals directly impacts the success of the company's end-to-end travel services and the overall satisfaction of participants.
    Charles Cannella

    Kristen Williams - President, Brand

    Kristen Williams, the President, Brand at awayday, architects the overarching brand strategy and market positioning for the company's diverse travel offerings. By defining the core values and messaging that differentiate the company in the hospitality sector, the President, Brand ensures that every client interaction reflects the commitment to meaningful connection. Williams oversees marketing initiatives and public relations efforts to expand the company's reach among corporate and social groups. Kristen Williams collaborates with other executives to ensure that the brand promise is consistently delivered through every trip execution. This role involves analyzing consumer behavior to identify new opportunities for growth and service innovation. By maintaining a strong brand identity, the President, Brand fosters trust and loyalty among clients. Through strategic oversight of brand assets and communications, the President, Brand drives the company's reputation as a premier partner for organizations and groups seeking transformative shared experiences.

    Rj McClure - President, Brand

    Rj McClure, the President, Brand at awayday, focuses on the development and implementation of experiential marketing strategies that highlight the company's unique value proposition. By crafting compelling narratives around the company's curated travel experiences, the President, Brand drives engagement with potential corporate and social clients. McClure manages the creative direction of the brand to ensure that all materials and digital presence align with the company's mission of fostering genuine connection. Rj McClure works with the operations team to translate brand promises into tangible trip experiences that exceed client expectations. This role involves monitoring industry trends to keep the brand relevant and competitive in the evolving travel market. By fostering partnerships with influencers and industry leaders, the President, Brand expands the company's visibility. Through a focus on brand consistency and innovation, the President, Brand supports the company's growth and its status as a leader in group 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 Dan Yankley (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), Dan Yankley (Chief Operating Officer) and other senior executives.
    How many executives does awayday have?
    awayday has 8 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, Chief Operating Officer, Drove Organic & Inorganic Ebitda Growth For PE-Backed Portfolio Company, Regional President, Brand.