Chief of Staff

ABOUT PENNY JAR

Penny Jar is an early-stage venture capital firm that partners with founders building enduring companies across industries. We believe success is built through consistent, collective effort, one “penny in the jar” at a time. Our approach is founder-first, high-conviction, and hands-on, with a growing platform that leverages networks, operational expertise, and technology to support entrepreneurs at every step. We’ve invested in companies like Assured, Compa, Nue, Syndio, Upwind, and Zafran.  

We are building a team and a portfolio of companies rooted in imagination, curiosity, and determination. We believe that diverse experiences, backgrounds, and perspectives are critical to building a winning culture at Penny Jar, both within our firm and across our portfolio. Even if you don’t meet every qualification listed, we encourage you to apply.

If you are interested in applying, please fill out our Chief of Staff Interest Form.

THE OPPORTUNITY

We are seeking a high-impact, driven, entrepreneurial Chief of Staff to work directly with the managing partners (Bryant and Rich) across all aspects of the firm. 

The ideal candidate is both a natural leader and a tactical doer. Someone who thrives in ambiguity, loves turning chaos into structure, and brings an intellectual curiosity to early-stage venture capital.

This role will serve as a trusted partner to the managing partners across key areas of internal operations, portfolio company and founder support, community and advisor network engagement, internal systems development, investor relations, and strategic initiatives.

RESPONSIBILITIES

You’ll work across a range of priorities that will evolve over time. Core areas of ownership at the outset include:

  • Founder Support: Supercharge Penny Jar’s ability to serve our portfolio companies by ensuring operational excellence, strategic responsiveness, and consistent value creation.
  • Collective Enablement: Maximize Penny Jar’s Collective, a curated group of advisors and C-Suite leaders, by helping organize, activate, and leverage this community to support founders, foster meaningful relationships, and extend Penny Jar’s reach.
  • Internal Systems Building: Lead the development of Penny Jar’s internal operating system, ensuring our AI tooling connects seamlessly to the team’s workflows and investment activities.
  • Investor Relations: Lead writing of limited partner (investor) updates, monthly newsletters, and other firm communications.
  • Strategic Initiatives: Take ownership of ad-hoc initiatives across product development, brand building, community engagement, operational improvement, and events.
  • Partner Support:  Serve as a trusted extension of the managing partners, helping translate vision into execution.

QUALIFICATIONS

Education: Bachelor’s degree required.

Work Experience: 

  • 3-5 years of relevant professional experience. Ideal backgrounds include management consulting, startup operations, venture capital, or related fields.
  • Strong track record of thriving in fast-paced, high-performance environments.
  • Open to high-performing generalists with demonstrated initiative and results orientation.

Key Skills and Attributes:

  • Exceptional Communicator: Excellent written and verbal communication skills, paired with strong emotional intelligence (EQ).
  • Creative Thinker: Natural curiosity and outside-the-box thinking that empowers you to tackle ambiguous, complex challenges.
  • Self-Starter: Highly proactive, motivated to bring solutions to the table, not just surfacing issues.
  • Organized Operator: World-class project management skills and strict attention to detail.
  • Community-Oriented Mindset: Naturally builds and nurtures relationships across diverse stakeholders, from founders to advisors to investors, with empathy, trust, and follow-through.
  • Comfortable in Complexity: Thrives in unstructured environments and adapts quickly to ad-hoc initiatives.
  • Technologically Fluent: Comfortable using AI tools and modern technology to streamline work and create leverage.
  • Excellent Peripheral Vision: Demonstrates an ability to anticipate and head off challenges.

Why JOIN PENNY JAR

  • Active seat at the table: Play an impactful role working alongside firm leadership and top founders, contributing directly to early-stage investing and company building.
  • Functional breadth: Opportunity to engage across operations, product, brand, and AI initiatives.
  • Hands-on AI exposure: Firsthand experience building and deploying agentic AI systems inside a venture platform.
  • Growth trajectory: Opportunity to grow within Penny Jar with increasing ownership and leadership potential.
  • Culture: Sharp, ambitious, gritty, yet approachable and collaborative. We are serious about our work but not about ourselves. We believe strong communities are essential to long-term success.

Logistics

  • Location: Bay Area-based; hybrid remote work model (combination of in-office and work-from-home).
  • Travel: Occasional travel for events or founder-related activities; not expected to be material.
  • Compensation: Competitive pay will be offered commensurate with qualifications, and competitive benefits will be provided, including comprehensive medical plans, 401(k) plan, and flexible time off.

How to Apply

If this sounds like you, a builder, a doer, a sharp thinker excited to dive into ambiguity and create lasting impact, we’d love to hear from you. Share your interest here: Chief of Staff Interest Form.