Hilltop Executive and Leadership Team

September, 2026

Leadership Overview

Hilltop has 4 executives leading key functions including strategic oversight, operational management, financial planning, and human capital development.

Dedicated to enhancing lives across Western Colorado, Hilltop delivers essential transitional living, assisted living, and specialized memory care services to diverse populations throughout the region.

Leadership Roles at Hilltop

  • Chief Executive Officer - William (Will) Hays
  • Chief Financial Officer - Ashley Guggemos
  • Chief People Officer - Rebecca Weitzel
  • Deputy Director - Sherry Price
  • William (Will) Hays - Chief Executive Officer

    William (Will) Hays, the Chief Executive Officer at Hilltop, directs the overarching strategic vision for all health and community service initiatives. Overseeing the expansion of transitional living programs, the Chief Executive Officer ensures alignment between organizational goals and the evolving needs of Western Colorado residents. This leadership role involves constant collaboration with the Board to maintain high standards in assisted living and Alzheimer's care. By optimizing service delivery models, William (Will) Hays directly impacts the quality of life for thousands of individuals. The Chief Executive Officer manages complex stakeholder relationships to secure long-term sustainability for the organization. Through rigorous oversight of regional operations, the Chief Executive Officer drives excellence across every department. Ultimately, Hays secures the future of the company by fostering innovation in community-based health services and maintaining a steadfast commitment to the mission of providing comprehensive support resources.

    Ashley Guggemos - Chief Financial Officer

    Ashley Guggemos, the Chief Financial Officer at Hilltop, architects the fiscal strategy and manages the capital structure necessary to support diverse health service programs. Overseeing budgeting, financial reporting, and revenue cycle management, the Chief Financial Officer ensures the long-term economic viability of all transitional and assisted living initiatives. This leadership role involves analyzing market trends in Western Colorado to inform investment decisions and resource distribution. Ashley Guggemos maintains transparency with the Board regarding financial health and risk mitigation strategies. By optimizing cost structures, the Chief Financial Officer enables the organization to reinvest in critical care infrastructure and staff development. The Chief Financial Officer coordinates with other executives to align financial goals with the mission of providing accessible community resources. Through precise fiscal planning, Guggemos secures the necessary funding to sustain high-quality care standards. Ultimately, the Chief Financial Officer drives financial stability and growth for the entire organization.
    Ashley Guggemos

    Rebecca Weitzel - Chief People Officer

    Rebecca Weitzel, the Chief People Officer at Hilltop, directs human capital strategy, talent acquisition, and organizational culture initiatives. Overseeing the recruitment and retention of specialized staff for Alzheimer's care and assisted living programs, the Chief People Officer ensures the workforce remains highly skilled and motivated. This leadership role involves designing comprehensive training programs that align with the specific health service needs of the Western Colorado community. Rebecca Weitzel manages employee relations and performance management systems to foster a culture of excellence and compassion. By implementing robust talent development frameworks, the Chief People Officer supports the operational success of every department. The Chief People Officer collaborates with the executive team to ensure that staffing levels meet the demands of expanding service offerings. Through strategic workforce planning, Weitzel strengthens the internal capacity of the organization. Ultimately, the Chief People Officer drives employee engagement and organizational health to support the mission.

    Sherry Price - Deputy Director

    Sherry Price, the Deputy Director at Hilltop, manages daily operational workflows and coordinates cross-departmental efforts to ensure seamless service delivery. Focusing on the execution of assisted living and memory care protocols, the Deputy Director maintains strict adherence to regulatory standards across all facilities. This role involves bridging the gap between executive strategy and frontline implementation to maximize efficiency. Sherry Price monitors performance metrics to identify areas for operational improvement within the Western Colorado service network. By streamlining internal processes, the Deputy Director supports the broader organizational objective of providing high-quality care to aging populations. The Deputy Director collaborates with department heads to resolve logistical challenges and improve resource allocation. Through consistent monitoring of service quality, Price ensures that every program meets the rigorous demands of the community. Ultimately, the Deputy Director stabilizes the operational foundation required for the company to scale its impact effectively.

    Frequently Asked Questions Regarding Hilltop Top Executives and Leadership Team

    Who leads Hilltop?
    Hilltop is led by William (Will) Hays (Chief Executive Officer), along with executives such as Ashley Guggemos (Chief Financial Officer) and Rebecca Weitzel (Chief People Officer).
    Who is part of Hilltop’s executive team?
    The executive team of Hilltop includes leaders such as William (Will) Hays (Chief Executive Officer), Ashley Guggemos (Chief Financial Officer), Rebecca Weitzel (Chief People Officer) and other senior executives.
    How many executives does Hilltop have?
    Hilltop has 4 executives leading key business areas.
    What roles are included in Hilltop’s leadership team?
    The leadership team of Hilltop includes roles such as Chief Executive Officer, Chief Financial Officer, Chief People Officer, Deputy Director.