In 2021, raising a round often felt like surfing a wave: you just had to stand up and hold on. Capital was abundant, valuations soared, and timelines from first meeting to term sheet were measured in days. Four years later, the tide has gone out. In the past year, we have seen a monumental shift … Continued
Imagine making billion-dollar decisions based on data 6-12 months old. To Charlie Franklin, this wasn’t just illogical—it was negligent. As a career-long compensation expert, Charlie experienced a glaring paradox: compensation was the single most significant expense for most companies, yet these massive investment decisions were being guided by data that traveled so slowly, a carrier … Continued
I haven’t written code in 15 years, but I just built a retrieval engine in five minutes, thanks to Ducky. In college, I studied engineering, but like any good engineer, I went into investment banking after graduating (hopefully, you can feel the sarcasm oozing through the screen). So, it’s been a minute since I even … Continued
Building a company is all about human capital. People create products and sell them to other…people. Even in the age of AI, people sit at the core of every company, yet hiring excellent talent is the single most challenging element of a business to do well consistently. It’s also critical to building a company at … Continued
With the explosion of data inside organizations and the proliferation of SaaS applications, employees are struggling to stay afloat at work. In a 2021 study, McKinsey found that the average company uses over 100 different SaaS applications (up from only 8 in 2015), and knowledge workers spend ~20% of their time searching for internal information. … Continued
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
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
We’re excited to announce our recent investment in Nue, a modern quote-to-revenue platform designed to help businesses drive revenue and retain customers in an increasingly dynamic economy. In today’s competitive marketplace, businesses must be able to support a broad range of pricing models. As companies look to meet the needs of their customers, one size … Continued