Dustin Kress

Helping school districts achieve efficient, effective and safe transportation- Director, RouteWise AI, HopSkipDrive

Denver, Colorado, United States

About

Operations leader with a history of achieving results in Education and Government Administration. A team builder with a focus on strategic planning, stakeholder engagement, and coaching to improve experience and outcomes. Thoughtful, empathetic, fun.

Experience

  • HopSkipDrive (Full-time · 2 yrs 11 mos)
    • General Manager, RouteWise AI
      Oct 2025 - Present · 9 mos

    • Director, RouteWise AI
      Aug 2023 - Oct 2025 · 2 yrs 3 mos

      Lead the strategic vision and implementation of AI-powered transportation solutions with school districts across the county.

  • Chief Of Staff at Denver Public Library
    2022 - 2023 · 1 yr

    Responsible for day-to-day operations and decision making of the organization including supervision and coaching for 7 library directors, planning and facilitation of executive meetings, sponsorship and evaluation of priority initiatives, and reporting to Library Commission oversight body - Redevelop the organization’s HR and EDI departments following significant turnover including selecting new leaders and establishing vision and priorities for departments - Sponsor strategic planning and implementation for successful property tax ballot initiative increasing Library revenues 60%; on track to hire 140 new FTE’s in 2023

  • Denver Public Schools (9 yrs 1 mo)
    • Chief of Staff - Operations Division
      2019 - 2022 · 3 yrs

      Responsible for administration of the Operations leadership team, management of strategic initiatives and internal communications. This included differentiated support and coaching for all executive directors particularly as it relates to large change management initiatives or initiatives of political concern - Managed initiative to reduce transportation driver FTE needs by 15%; this was a systems optimization project as well as a large change management effort due widespread dependencies on bell times. - Established Service Level Agreements between each operations department and schools to serve as service commitments and a tool for regular, informed progress monitoring

    • Associate Director of Special Projects
      2017 - 2019 · 2 yrs

      Responsible for priority Superintendent initiative along with facilitation of Senior Leadership meetings and Board of Education meetings. This included facilitation and leadership of 40-person community group over the course of two years charged by the Board of Education with developing a plan to increase school integration and address declining enrollment. - Presented strategic recommendations to the Board of Education followed by detailed implementation proposals - Solicited support from local foundations to grow initiative budget by 50% (+$25,000) and managed grant budget

    • Senior Manager/Manager of Bond and Mill Levy Programs
      2013 - 2017 · 4 yrs

      Responsible for internal planning and external oversight associated with regular voter tax requests. This included the management of two standing external oversight bodies as well as a one-time 70-person capital planning committee. Responsible for internal management and strategy setting for staff requests for capital planning committee -Managed the implementation of $50m in 2016 Mill Levy projects including the development of investment strategy, budget allocations, and evaluation metrics and processes - Led strategic planning, internal communications and change management associated with the The Denver Plan 2020

  • Senior Consultant / Consultant at Monitor Deloitte
    2010 - 2013 · 3 yrs

    Responsible for analytics, presentation development and meeting facilitation associated with client objectives. Supported clients with a focus in healthcare and life sciences with additional project work in CPG and defense. - Developed global brand strategy for the launch of two new multiple sclerosis treatments; this included the facilitation of two international scenario planning exercises - Led the product integration and launch for a major health insurer introducing a new Wellness offering