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Chief of Staff

Allup

Allup

People & HR, Operations
Boston, MA, USA
Posted on Mar 22, 2025

About our client

Alpaca VC is an all-grit, no-BS team of six investors who are committed to finding and supporting the best founders throughout the formative years of the startup lifecycle. It is a highly engaged team that blends collaboration and autonomy, and values results and learning over rigid office hours. Everyone on the team is a solo-preneur, yet no one hesitates to ask for help or assistance.

Alpaca VC has been lucky to partner with top portfolio companies, including Compass, Sandbox, Latch, Imperfect Foods, Upstream, Transfix, FirstBase, Monument, and more.

About the role

An Alpaca Executive building an innovative asset management business at the intersection of real estate and technology is looking for a rockstar executive business partner Chief of Staff to help with day-to-day operational tasks and business execution.

This role combines core Executive Assistant responsibilities—including inbox management, calendar coordination, travel arrangements, and team offsite planning—with Chief of Staff duties such as overseeing and managing projects, organizing and creating priorities aligned with annual and quarterly OKRs, ensuring thorough followthrough on action items, and providing support for investor relations activities.

The ideal candidate is extremely organized, proactively looks ahead to what’s coming next, and is willing to roll up their sleeves and pitch in wherever needed. The executive operates with a small team and you will have an outsized impact on the success of their endeavors. This role can be executed remote (ET, CT, MT time zones) or in-person (Aspen, CO). Great benefits, and 401k with match.

Responsibilities:

  • Manage and track OKRs and KPIs, proactively setting daily and weekly priorities aligned with quarterly and annual goals, organizing pre-work, and ensuring thorough follow-up on action items.
  • Proficiently utilize project management tools (Notion, Salesforce, etc.) to track projects, manage workflows, and maintain operational efficiency.
  • Manage the Executive's complex and busy calendar. Proactively optimize calendar.
  • Organize email inboxes, prepare responses where appropriate and track items requiring follow-up.
  • Coordinate and manage domestic and international travel schedules as needed.
  • Plan team events and off-sites to build company culture.
  • Provide meeting support through attending meetings, taking notes, writing action items, and noting follow-up items.
  • Facilitate stakeholder communication.
  • Maintain confidentiality and discretion.
  • Anticipate the needs of the Executive. Plan ahead and be resourceful.
  • Prioritize and resolve conflicting needs with little to no guidance.

Qualifications:

  • Previous experience supporting an executive in a fast-paced environment.
  • Excellent verbal and communication skills.
  • Great attention to detail and organizational skills.
  • Proactive, flexible, and able to take initiative as needed. You are able to do the research, use AI as a thought partner and generate ideas.
  • High EQ.
  • Work well under pressure in a fast-paced time-sensitive environment. Ability to switch gears and adapt to changes as priorities pivot.
  • Able to multitask, look ahead, and bring a framework to the role in terms of organizational processes.
  • Tech-savvy, with a curiosity for implementing AI as appropriate
  • Ability to learn new tools quickly and become Notion power user.

Salary: $130k-180k/year