About the Role

We are seeking a detail-oriented, strategic, people-first and mission-driven individual to join our incredible team as an Executive Assistant to the Chief Executive Officer, Chief Operating Officer, and Chief Medical Officer.

This individual will be responsible for supporting Hopscotch Health's C-suite in all aspects of their day-to-day, week-to-week and month-to-month management and leadership of the business, including leading efforts around planning, preparation, people enablement and coordination, and time management. The Executive Assistant will serve as a trusted partner and advocate to deliver against the priorities of the business and support the team and culture of Hopscotch too.

The Executive Assistant will play a dynamic role in coordinating and managing executive calendars to drive progress against key priorities, ensure effective and efficient use of time across senior leadership, and support engagement and preparation across internal and external meetings as well as travel.

What You'll Do

Specific responsibilities for this role will include, but are not limited to:

• Support effective and efficient use of time for the CEO, CMO, and COO relative to key organizational priorities for the business and culture through calendar and time management, prioritization, logistical planning, and preparation
  • Drive day-to-day and week-to-week management of time and logistics (travel, expenses, technology) against key priorities, for individual leaders and for the organization, through calendar management, preparation, coordination, and communication, with the C-suite and with others across the team
  • Proactively manage the CEO, CMO and COO's calendars, including scheduling meetings (internal and external), appointments, speaking engagements, and travel, leveraging strong organization, preparation, collaboration, and communication to optimize
  • Serve as the primary liaison between the C-suite and internal and external parties on all matters, including highly confidential and sensitive matters, demonstrating leadership to maintain trust, credibility, and advocacy for the executive team
  • Coordinate among internal team members and external stakeholders to set expectations for meetings and ensure preparation allows for successful engagement, including the executive support team for the BOD and external executives
  • Coordinate with team members and external stakeholders to prepare and confirm meeting logistics (i.e., Zoom link vs. meeting location/room vs. phone call), an agenda and clear set of objectives, and meeting materials
  • Maintain a list of in-flight scheduling and planning tasks and be able to prioritize and communicate these items clearly, quickly, and effectively to leadership

• Support the on-going support and engagement of existing team members as well as the on-boarding for new team members reporting to the C-suite, acting as onboarding liaison and concierge for new team members that will report directly to the executive team
  • Proactively plan for calendar and time to ensure that C-suite teams have the support and time they need to enable their success and engagement in their roles
  • Support Hopscotch culture, through efforts to drive on-going engagement and collaboration of the Hopscotch team (in-person and remote & field/market vs. Corporate)
  • Support scoping and development of roles reporting directly to the CEO, CMO, COO, and broader C-suite over time and partner with the talent acquisition and people operations team to ensure a smooth onboarding and transition process for direct reports
  • Develop key onboarding and mobilization materials and toolkits for direct reports to the C-suite, help guide new hires through first few weeks and months of their transition onto the team including preparing a schedule and set of resources to enable a successful ramp up

• Enable successful internal and external engagement with the C-suite through coordination and preparation, including BOD meetings, town hall meetings, conferences and key internal engagement
  • Drive preparation and timing for agendas, objectives, meeting materials, and/or activities for engagements, and coordinate amongst internal team members and external stakeholders to ensure accountable parties execute on their responsibilities to ensure effective use of time
  • Coordinate travel and any other logistics (meeting rooms, catering, technology) to support meetings and engagement
  • Support program management required to coordinate broader team events, including full team in-person meetings, monthly team check ins, and team social events
  • Where appropriate, attend meetings and capture notes, consolidate, and synthesize, communicate to broader team and other stakeholders, and ensure follow up occurs through a robust process to identify next steps, assign an owner, delegate responsibilities to the appropriate team member including other executives, tag a date/trigger to revisit, and track follow up / signal when it needs to be brought back up to team
  • Prepare and distribute communications on behalf of the C-suite, for internal and external audiences
  • Maintain a high level of professionalism and confidentiality in and outside of meetings with meeting content, discussions, and other sensitive information
  • Maintain a list of key stakeholders and contacts for the C-suite to support external and on-going engagement for Hopscotch C-leaders

• Provide additional support for program management and other foundational tasks where needed, including project planning, intake, prioritization, initiation, execution, and training; always lean in with a team-first attitude to support others and enable progress towards our big and important mission

About You

You would be a great fit for this position if you have 5-10+ years of experience as an Executive Assistant for C-suite leadership, ideally at a high-growth company with advanced calendar and program management experience, and you:

• Have demonstrated motivation, perseverance, and confidence by solving problems, planning proactively, taking initiative, and delivering results by operating with autonomy
• Demonstrate exceptional leadership skills with an ability to drive initiatives forward and establish trusted relationships amongst executives and a wide range of stakeholders
• Execute and operate at a fast pace, bring focus and structure to situations as needed and manage well in fast-paced and/or higher-pressure circumstances
• Are an innovative and creative thinker who can quickly and effectively identify new and better ways of working and suggest sustainable and scalable solutions
• Have exemplary time management skills and the ability to identify and anticipate executives' needs
• Are proactive, organized and incredibly responsive and have strong reporting and management skills
• Can interact seamlessly and with a high level of professionalism across a broad range of individuals including senior leadership at Hopscotch and external executives and other stakeholders
• Bring passion for a mission-driven organization and show a willingness to 'go the extra mile' to do whatever work is needed for the cause and for the team
• Bring a high attention to detail and a drive for execution and results, using both to propel results in your work and collaboration
• Bring a high IQ and EQ, showing an ability to learn and to navigate complicated interpersonal dynamics and collaborate to get work done
• Leverage synthesized communication, written and verbal, to engage senior leaders, demonstrating a command for ability to communicate priorities, risks, and action plans clearly and succinctly in multiple formats (i.e. emails, PowerPoint, dashboards)

From a cultural perspective, you are:

• Agile, yet thoughtful and can work effectively in a fast-paced, ever-changing environment
• Constantly seeking ways to simplify and improve how things are done, bringing a positive attitude to challenges
• Accountable, holding yourself and others to a high standard and seek to support and develop others
• Willing to roll up your sleeves to support the work required and collaborate effectively with people of all backgrounds
• Concise and articulate, drive towards clarity and deliver on your commitments
• Collaborative, assuming positive intentions
• Customer-focused, with a passion for serving patients and providers who make healthcare possible