Penny Jar Capital
Principal Role Job Description
February 2026
About Penny Jar
Penny Jar Capital is an early-stage venture firm investing in B2B software and AI-driven companies building category-leading businesses across large, overlooked industries. Founded by Bryant Barr and Rich Scudellari, Penny Jar partners closely with founders from the earliest stages—often leading or co-leading rounds and building meaningful ownership positions.
The firm has backed companies including Assured, Compa, Upwind, and Zafran. Penny Jar’s first fund (2021 vintage) is a top-decile performer, and the firm is actively deploying its second fund.
Penny Jar combines institutional-grade diligence with a differentiated ecosystem of operators, customers, advisors, and investors that supports founders across go-to-market execution, enterprise adoption, hiring, and follow-on fundraising. The firm operates as a small, high-conviction team based in the San Francisco Bay Area.
Position Overview
Penny Jar is seeking to hire a Principal to identify and partner with the next generation of category-defining founders. This role is simple: find exceptional founders and partner with them. It’s designed for an entrepreneurial investor who wants to take meaningful ownership of sourcing, build on a top decile inaugural fund, and actively shape a growing venture firm.
As a Principal, you will work directly with the firm’s partners across all aspects of investing—from initial founder engagement through investment execution and portfolio support. The role offers significant autonomy alongside close collaboration in a high-trust, high-responsibility environment.
Responsibilities
- Deal Sourcing: Proactively originate and build a high-quality pipeline of early-stage investment opportunities through deep relationships with founders, operators, investors, and startup ecosystems, while contributing to thematic investment area development and sourcing strategy. This is the role’s primary mandate.
C O N F I D E N T I A L & P R O P R I E T A R Y
Principal Role Job Description (2026)
- Pipeline Development & Management: Strengthen Penny Jar’s long-term positioning with high-conviction founders by cultivating durable relationships, maintaining consistent engagement across priority sectors and communities, and reinforcing Penny Jar’s reputation as a preferred early partner.
- Deal Evaluation & Diligence: Lead evaluation and diligence efforts for sourced opportunities, including developing investment theses, leading market and product analysis, facilitating customer and industry references, and assessing competitive positioning and financial scenarios.
- Investment Process Leadership: Lead internal deal processes from initial engagement through Investment Committee, helping build conviction across the partnership, preparing investment memos, coordinating internal discussions, and presenting recommendations to partners.
- Ecosystem & Investor Relationship Building: Develop and maintain relationships with venture firms, operators, and angel investors to expand Penny Jar’s sourcing network, support founder fundraising, and enhance co-investment opportunities.
Qualifications
- Experience: 2–4+ years of experience in early-stage venture investing, startup operating roles, or related positions with strong exposure to founders and the technology ecosystem.
- Sourcing Ability & Network: Demonstrated ability to build relationships with founders, operators, and investors that generate high-quality early-stage investment opportunities. ● Investment Judgment & Curiosity: Strong critical thinking and pattern recognition with the ability to evaluate early-stage companies in ambiguous and evolving markets. ● Relationship Builder: Exceptional interpersonal and communication skills with the ability to build trust and credibility with founders and co-investors.
- Ownership Mentality: Self-starter who thrives with autonomy and is motivated to develop sourcing channels and long-term investment outcomes.
- Analytical Capability: Comfort evaluating markets, business models, product differentiation, and financial scenarios.
- Intellectual Ownership & Perspective: Demonstrates independent thinking and develops clear, well-supported viewpoints on markets, companies, and investment decisions, with the confidence to thoughtfully debate and defend those perspectives in collaborative partner discussions.
- Industry Alignment: Strong interest in B2B software, vertical software, and AI-driven businesses.
- Location: Based in or willing to relocate to the San Francisco Bay Area. C O N F I D E N T I A L & P R O P R I E T A R Y 2
Principal Role Job Description (2026)
We are committed to creating a diverse and inclusive workplace. We believe that a range of perspectives and experiences leads to better decisions, stronger partnerships, and better outcomes for the founders we support. Even if you don’t meet every qualification listed, we encourage you to apply.
C O N F I D E N T I A L & P R O P R I E T A R Y 3
