This week, Penny Jar hosted Innovation in the Enterprise in Milwaukee, an event focused on how technological transformations are reshaping large companies. The panels, discussions, and questions around innovation in the enterprise were vibrant, the insights were profound, and the enthusiasm was palpable. We were fortunate to bring Penny Jar founders together with industry leaders … Continued

Maria Colacurcio is a passionate entrepreneur with a strong background in both founding and leading innovative companies. Raised in an environment that encouraged pushing boundaries and embracing challenges, Maria’s journey in the tech industry began with her role as co-founder at Smartsheet, which successfully went public in 2018. Her experiences there, combined with her desire … Continued

Svanika Balasubramanian is a visionary entrepreneur whose background and career are rooted in her commitment to creating impactful change. Born in India and raised in Oman, Svanika’s family has a rich history of activism. Despite their efforts, she observed limitations in achieving widespread impact through non-profit work alone. This realization propelled her to pursue studies … Continued

In the rapidly evolving cyber threat landscape, security teams are struggling to keep pace with attackers who exploit new vulnerabilities within mere minutes of their discovery. This contrasts with the weeks or months typically required for vulnerability remediation and patching, leaving organizations dangerously exposed during this critical window. Recent reports reveal that 60% of data … Continued

Compensation dominates the income statement. With headcount comprising up to 70% of a company’s total operating expense, a tremendous amount of scrutiny is put on compensation. Not only is compensation a huge expense for a business, but it’s also one of the most sensitive and hotly contested topics. The interesting thing about compensation is that … Continued

As 2023 comes to a close, we were fortunate to host many of our founders, investors, business partners, and friends at Penny Jar Capital’s holiday party in San Francisco. The gathering was a wonderful opportunity to reflect on the year and bring together the people who’ve been with us every step along the way. The … Continued

At Penny Jar, we always seek opportunities to connect our innovative founders with executives at industry-leading enterprises. It’s gratifying when we can facilitate these connections in person. Given I (Rich) am in Milwaukee, we’ve been fortunate to develop relationships with some incredible corporations, including Northwestern Mutual, Molson Coors, and GE, all of which have been … Continued

Cloud-native technology has transformed the way businesses operate. It has enabled companies to build and deploy applications quickly and efficiently while providing significant cost savings. However, the rapid adoption of cloud-native technology brings new security challenges, as traditional solutions are unsuitable for constantly evolving cloud environments. That’s where Upwind comes in. Their platform offers dynamic, … Continued

Headcount can comprise up to 70% of a company’s total operating expense. For a cost of that magnitude, you would expect organizations big and small to have sophisticated tools and resources to accurately manage and forecast their greatest asset – people.  Despite the litany of financial planning and analysis (FP&A) software solutions available to today, … Continued

The world’s plastic problem is monstrous. Every minute the equivalent of one garbage truck of plastic is dumped into our ocean. Only a small fraction (~9%) of the world’s plastic is recycled. The rest? Well, most of that ends up in the environment, either in landfills, waterways, or other unintended places. It’s a problem so … Continued