Principal

<p><b>Principal Role Job Description </b></p> <p><span style="font-weight: 400">February 2026 </span></p> <p><b>About Penny Jar </b></p> <p><span style="font-weight: 400">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. </span></p> <p><span style="font-weight: 400">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. </span></p> <p><span style="font-weight: 400">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. </span></p> <p><b>Position Overview </b></p> <p><span style="font-weight: 400">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. </span></p> <p><span style="font-weight: 400">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. </span></p> <p><b>Responsibilities </b></p> <ul> <li><b>Deal Sourcing: </b><span style="font-weight: 400">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. </span></li> </ul> <p><b>C O N F I D E N T I A L &amp; P R O P R I E T A R Y</b><b><br /> </b></p> <p><span style="font-weight: 400">Principal Role Job Description (2026) </span></p> <ul> <li><b>Pipeline Development &amp; Management: </b><span style="font-weight: 400">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. </span></li> <li><b>Deal Evaluation &amp; Diligence: </b><span style="font-weight: 400">Lead evaluation and diligence efforts f...