Full-time | Tysons, Virginia

As Chief of Staff, you will provide high-level support to an ultra-high-net-wealth (UHNW) entrepreneur, with an emphasis on: (1) business analysis and development; (2) business relationship management; (3) brand management; (4) entrepreneurial scheduling and administration; (5) special projects; and (6) resource coordination.  This role is much more than a gatekeeper, scheduler, and administrative assistant—to excel, you must be multi-faceted servant leader who is passionate about becoming a force multiplier for a successful entrepreneur.

Essential functions of this role will include:

  • Business Analysis and Development
    • Identify business growth and development opportunities within entrepreneur’s network and enable the entrepreneur to efficiently and effectively follow up with such opportunities.
    • Prepare entrepreneur for meetings with research and analysis; take in-meeting notes when required; prepare and draft post-meeting correspondence, synthesizing potential paths forward; track follow-up items.
    • Read and screen incoming emails and other correspondence, use judgment and discretion to assess the importance of the materials, flag important items for entrepreneur’s attention.
    • Compose emails, letters, and other correspondence in response to incoming email, calls, or participation in meetings.
  • Business Relationship Management
    • Maintain a personal Contact Relationship Management system for the entrepreneur, including ensuring accurate and up-to-date information for contacts.
    • Identify ways entrepreneur can assist and add value to their network of contacts.
    • Monitor all media for items of interest to the entrepreneur and their network of contacts.
    • Draft personalized hand-written notes while ensuring timely delivery.
  • Brand Management
    • Assist entrepreneur with management of their social media accounts and online presence.
  • Scheduling and Administration
    • Perform scheduling and administrative tasks for the entrepreneur, including:
      • Track inbound requests for entrepreneur’s time and schedules follow-ups to such requests.
      • Update entrepreneur on status of issues and ensure entrepreneur has applicable information before scheduled meetings.
      • Assist entrepreneur with calendar coordination as requested.
      • Assist with arranging travel schedule, itineraries and agendas, and reservations as requested.
      • Complete monthly expense reports.
      • Proofread written work and corporate materials.
  • Special Projects
    • Plan and coordinate special events.
    • Complete other professional and personal projects as assigned.
  • Resource Coordination
    • Manage outside consultants hired in support of above tasks.
    • Manage budgets for above tasks.
    • Manage interns supporting above tasks.

Skills that would be an asset to this position include:

  • Entrepreneurial mindset: Possess innate desire to initiate, improvise, adapt, take risks, overcome mistakes, learn, and persevere. Self-motivation with a strong sense of accountability.
  • Ability to support a non-linear thinker: Willing and able to point out other considerations not taken into account and set appropriate boundaries to help entrepreneur maximize time and resources.
  • Strong organizational skills: Ability to leverage technology to store, retrieve, and analyze complex data sets.  Effective at project management. Possess the ability to proactively manage the time and attention of a busy entrepreneur.
  • Strong interpersonal skills: Ability to learn and discern connectivity among centers of influence. Comfortable in social settings with business, military, and political leaders. Aptitude for building and nurturing professional relationships. Comfort with and understanding of proper protocols.
  • Adaptability: Adapt to change and different ways of doing things quickly and positively. Address setbacks or ambiguity quickly and calmly. Effectively work with a variety of people and situations.
  • Accountability: Accept full responsibility for self and contributions. Display discretion, honesty, and truthfulness.
  • Proactive critical thinking: Possess well-developed deductive reasoning and problem-solving skills. Able to identify an issue, dilemma, or problem, frame it as a specific question, then explore and evaluate information relevant to the question. Integrate multiple sources of information into development of a resolution. Possess polished written and oral communication skills.
  • Initiative-taking mentality: Recognize what needs to be done and accomplish it proactively and with minimal supervision.
  • Innovative mindset: Apply creative problem skills to develop multiple alternatives and understand the feasibility and cost/benefit analysis of each. Recognize and demonstrate the value in taking “smart” risks and learning from mistakes. Ensure areas for improvement are identified and addressed.
  • Results-oriented management: Define tasks and milestones to efficiently achieve objectives. Consistently meet deadlines and deliver accurate results.

Desired qualifications to apply for this position:

  • Bachelor’s degree.
  • Excellent Microsoft Office (Outlook, Word, Excel, and Power Point) skills.
  • Familiarity with CRM tools.
  • Experience with project management.
  • An unquestioned ability to use utmost discretion with confidential information.
  • Must pass background check and be eligible for security clearance.

This role is a full-time position. Days and hours of work are Monday through Friday, 9:00 a.m. to 6:00 p.m.  Occasional evening and weekend work and limited travel may be required as job duties demand.

To apply, please send your resume and cover letter to staffing@sentineltrust.com.

This job description does not list all job duties.  Occasionally, a supervisor or manager may request that you perform other duties.  Management’s evaluation of your performance is based on your performance of the tasks listed in this job description and these other duties.  Management has the right to revise this job description at any time.  This job description also is not a contract for employment.  Therefore, either you or the employer may terminate the employment relationship at any time, for any reason.

The Employer is an Equal Opportunity/Affirmative Action Employer and is committed to Diversity and Inclusion. They encourage diverse candidates to apply. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity, national origin, disability or veteran status. Veteran or Veteran Spouse preferred.