Ashley Cocciardi

“I was doing more than just the legal part. I became involved in the business side too. My skills grew in a different way with more business knowledge and more hands-on experience.” At the firm, Ashley was highly involved in side letter negotiations and managing investor obligations. She recalls, “We would agree to thing after thing in a side letter, and then I would worry: ‘who is making sure these things happen?” I started making spreadsheets that laid out our investor obligations and the department I thought should be in charge of tracking the obligation. It was the best I could do at the time.” Perpetually stressed by her increasing workload and the inefficiency of the fund’s patchwork management system, Ashley began searching for a solution. “I was constantly looking for a more automated system to ensure we weren’t in violation of our side letter agreements,” she remarked. “I wanted something that would allow us to track our side letter obligations and not rely so heavily on outside counsel.”

She was quickly convinced that Ontra’s Insight platform would provide her firm an efficient and scalable way to organize and manage their side letters and investor commitments. The firm agreed, and decided to partner with Ontra to implement Insight.

In her capacity as Associate General Counsel, Ashley managed the firm’s Insight onboarding and implementation process. During this period, Ashley saw firsthand how the attorneys in Ontra’s global network balanced successful legal careers with fulfilling personal lives in a post-pandemic world. As a mother of two, the prospect of having that same kind of work-life balance was very attractive to Ashley. She recalls thinking, “For the past two years, I’d been home all the time. We’d have breakfast, lunch and dinner together. I didn’t want to lose that by going back to the long commutes and 12 hour workdays.” That’s when Ashley realized Insight offered a twofold solution: it solved both the firm’s obligation management problem and provided her an opportunity to professionally pivot towards a more flexible, home-based labor-model. Over the course of the firm’s onboarding, Ashley became increasingly confident that partnering with Ontra would afford her the lifestyle changes she desired.

She now works approximately 15 hours a week on the Insight platform, reviewing and digitizing fund documentation, abstracting side letters and LPAs, and breaking out critical investor obligations. In her words, “It’s a very clear and easy way for me to not leave the industry. By working with Ontra, I can take advantage of my eight years of experience in a very specialized market while having the flexibility I was looking for.” She continues, “Self-employment always feels risky. But with Ontra, it felt like a safe risk.”

Ashley’s work-life balance has improved greatly since joining Ontra. She reflects, “At my former employment, I was balancing so much: having a demanding fulltime job and two children at home. So this feels easy!” With Insight, Ashley also has the flexibility to pursue her “passion project” of being a certified Doula. “I could never have done that in a traditional job,” she says. “Now, if somebody calls me to say they’re in labor, I can go and help because I have flexibility when it comes to the work I do.”

Ashley sees a bright future with Insight, stating: “I feel confident that I will step up my 15 hours at some point. Maybe when my youngest son is in school. The ability to do that is the awesome flexibility of Insight.”