How do you raise nine figures in financing in twelve hours as the first Twitter-fueled bank run is happening around you and you feel the pressure of hundreds and thousands of employees depending on your ability to finish the deal so their paychecks clear?Join Vanessa Wu, GC at Rippling, as she relives the moment her company overcame the disastrous collapse of Silicon Valley Bank and pulled through some lightning-fast deals to protect the income of the clients whose paychecks depend on them. Her department’s hard work turned a catastrophe into a boon to their company’s reputation, both with product users and investors.Listen as Vanessa offers a masterclass in getting financing and deals over the finish line in record time, with tips on moving through the diligence process, keeping fees low, and why it's essential for lawyers to close as quickly as possible.Read detailed summary:  https://www.spotdraft.com/podcast/episode-52Topics: Introduction: 0:00Becoming a top dealmaker at LiveRamp: 1:33Moving quickly to close deals: 7:06Offering operational solutions to small and medium businesses at Rippling: 10:08Surviving the collapse of Silicon Valley Bank: 23:14Collaborating with finance as a legal team: 36:21Tips for a fast and low-fee financing deal-making process: 40:54Favorite parts of day-to-day work: 41:54Book recommendations: 44:22What you wish you’d known as a young lawyer: 45:28Connect with us: Vanessa Wu: https://www.linkedin.com/in/vanessa-wu-7363359/  Tyler Finn: https://www.linkedin.com/in/tylerhfinn SpotDraft: https://www.linkedin.com/company/spotdraft  SpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues.   Visit https://www.spotdraft.com to learn more.

What do you need to know if you're considering taking on the people function? What's the difference between a chief people officer and a CHRO? And are GCs well-positioned to take on both of these roles simultaneously?Rachel Olchowka, Former Chief People Officer and General Counsel at Fetch and current Chief Administrative Officer at Prizm Insurance, had no hesitations when she volunteered to operate a complex, metrics-driven people function in addition to her responsibilities leading in-house legal at a fast-paced organization. Not only did she learn how to do both roles—she learned how to do them well.Listen as Rachel shares how she was able to find balance between two very different executive positions, know whether expanding into a people role is right for you, establish a game-changing comprehensive parental leave plan, craft culture within a company and executive team, and more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-51Topics:Introduction: 0:00Taking on the chief people officer role while serving as general counsel at Fetch: 2:25The difference between CPOs and CHROs: 5:25Encountering pushback from the executive team on HR policies: 9:01Crafting culture within an executive team: 12:35Establishing a comprehensive parental leave plan: 14:53Approaching the hiring process as a CPO: 19:38Comparing in-office policies against remote work: 24:40Dealing with emotionally charged issues in the CPO/CHRO role: 30:57Recommendations to GCs who want to take on multiple executive roles: 36:34Considering the right candidate for dual GC and CPO roles: 42:39Book recommendations: 46:37What you wish you’d known as a young lawyer: 50:19Connect with us:Rachel Olchowka - https://www.linkedin.com/in/rachel-olchowka/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading contract lifecycle management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you help CEOs transition out of the business? How do you project calm in a time of crisis? Can you draw on the experience of beating cancer twice as you navigate the challenges of executive leadership?  Dan Haley, General Counsel and Corporate Secretary at Guild, has led a career spanning the world of local Massachusetts politics, leading legal at companies like Sprinklr, and Athenahealth, enduring cancer treatments while holding high-stress leadership positions, and becoming known as legal’s most “zen” GC.  Listen as Dan shares how he developed his calming professional philosophy, why he wears t-shirts to work, and how he instills and nurtures a sense of confidence in his staff during trying times.  Read detailed summary:  https://www.spotdraft.com/podcast/episode-50   Topics: Introduction: 0:00 Balancing cancer treatment with a high-stress job: 9:21 Building a reputation as a zen lawyer: 12:23Maintaining a positive attitude and setting a tone as a GC role: 18:05Managing CEO transitions in a time of crisis: 23:16 Enduring a hostile takeover from Elliott Management at Athenahealth: 27:31 Facilitating the CEO transition at Athenahealth: 32:52 Facilitating the CEO transition at Guild: 37:22 Book recommendations: 46:14 What you wish you’d known as a young lawyer: 50:13  Connect with us:  Dan Haley - https://www.linkedin.com/in/danhaley1972/  Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft  SpotDraft is a leading Contract Lifecycle Management platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How is AI going to change the practice of law? How is one of the most forward looking law firms adapting? And will the billable hour go away?  Joe Green, Chief Innovation Officer at Gunderson Dettmer and Cofounder & Director of the Open Cap Table Coalition, steered a law career starting at major Wall Street firm Simpson Thacher towards the worlds of tech and product management, with stop-offs in academia and legal publishing along the way. Ultimately, he found that his legal mindset guided him in his technical work, and his understanding of business and innovation strengthened his legal abilities.  Listen as Joe discusses strategies to shift your careers towards your passion through pro bono work, stepping into board advisory roles, parsing the influx of investment into legal tech, and whether the billable hour will really go away in our lifetime.  Read detailed summary:  https://www.spotdraft.com/podcast/episode-49   Topics: Introduction: 0:00Moving into a tech advisor role at Gunderson Dettmer after a career start at Simpson Thacher: 2:11Moving away from the standard legal path at Thompson Reuters: 5:38Taking on side hustles that pull you towards tech and product: 8:43Founding the Open Cap Table Coalition: 11:59Rejoining Gunderson Dettmer and moving into the CIO role: 18:04Challenging the billable hour model: 20:56Leading and launching innovative projects: 30:06Shifting from a legal to a technical mindset: 33:44Discussing the influx of investment into legal tech: 37:20Predicting the future of legal services: 41:06Book Recommendations: 43:41What you wish you’d known as a young lawyer: 45:40 Connect with us: Joe Green - https://www.linkedin.com/in/joegreen1/  Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft   SpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you build a legal and business career from a passion for aviation? What is the transition like from the GC role to that of CEO? And what is it like to run an airline?  Ben Klein, CEO and First Officer at Aero, was able to combine his dedication to legal work with his lifelong love of flying. Starting off at big law firms like Davis Polk & Wardwell, he successfully transitioned into aviation law after founding his own firm, then took on GC roles at autonomous helicopter start-up Skyryse and Aero, an airline offering a private-jet-like experience.   Listen as Ben discusses instilling confidence in investors during a CEO transition, counseling his airline through the coronavirus pandemic, and leveraging his experience in the cockpit to make his company the best it can be.  Read detailed summary:  https://www.spotdraft.com/podcast/episode-48   Topics: Introduction: 0:00  Transitioning from corporate law to aviation law: 6:01Founding an aviation-focused law firm: 9:38Learning to manage an executive team as a first-time GC at Skyryse: 11:47Counseling an airline through the coronavirus pandemic: 14:57Taking on a GC and First Officer role at Aero: 16:09Leveraging your experience in the cockpit to lead as CEO: 23:59Instilling confidence in investors as you transition from GC to CEO: 25:47Inspiring teamwork in c-suite reports and hiring for your replacement GC: 30:58Book Recommendations: 35:30What you wish you’d known as a young lawyer: 38:49Connect with us: Ben Klein - https://www.linkedin.com/in/ben-klein-01b8736/  Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft  SpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How do you build trust with investors who tap you for the CEO role? How do you prepare yourself to lead companies through some of their toughest moments, including bankruptcy, and guide other companies through their transformations as a board member?Chelsea Grayson, managing partner of corporate restructuring at Pivot > and former CEO and board member of brands like American Apparel, True Religion, and Spark Networks, has steered many ships through rough waters, including post-chapter 11 turnarounds, corporate wind-downs, and firing CEOs for cause. She has transitioned from board member to operator and back again, and is currently sharing her expertise on the boards of Xponential Fitness and Beyond Meat.Listen as Chelsea discusses her legendary journey from law firm partner to GC, CEO, Board Member, and now managing partner of an all-star corporate restructuring company, and offers tips to lawyers who are looking to find a board seat.Read detailed summary:  https://www.spotdraft.com/podcast/episode-46Topics:Introduction: 0:00Rising to partner at Jones Day and Loeb & Loeb, two big LA-based law firms: 3:00Transition to in-house legal (and a CEO role) at American Apparel: 9:35Tips for building relationships with investors: 15:11Managing CEO transitions: 18:34Joining boards and positioning yourself as a good board member: 26:30Becoming CEO of True Religion Jeans during a turnaround: 34:19Sitting on the board of Sugarf ina after a bankruptcy turnaround: 37:45Stepping into a tech CEO role at Spark Networks: 42:00Founding Pivot >, a corporate restructuring company: 47:39Book recommendations: 55:08What you wish you’d known as a young lawyer: 58:10Connect with us:Chelsea Grayson: https://www.linkedin.com/in/chelseagrayson24/Tyler Finn: https://www.linkedin.com/in/tylerhfinnSpotDraft: https://www.linkedin.com/company/spotdraftSpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

Read detailed summary:  https://www.spotdraft.com/podcast/episode-46Topics: Introduction: 0:00Deanna Papedis on adopting a strategic mindset and keeping your eye on the big picture: 1:05Hardeep Singh on congratulating yourself when you reach a career milestone: 2:10Vineet Shahani on dealing with career lows and leaning on your communication skills: 3:50Nguyễn Vu on establishing strong relationships with people who can move the needle on your career: 6:09Sagi Eliyahu on knowing when the world is ready for your idea: 8:49Connect with us: Deanna Papedis - https://www.linkedin.com/in/deanna-papedis/ Hardeep Singh - https://www.linkedin.com/in/hardeep-singh-863b1617/ Vineet Shahani - https://www.linkedin.com/in/vineetshahani Nguyen Vu - https://www.linkedin.com/in/nguyentvu/  Sagi Eliyahu - https://www.linkedin.com/in/eliyahusagi/  Tyler Finn - https://www.linkedin.com/in/tylerhfinn SpotDraft - https://www.linkedin.com/company/spotdraft  SpotDraft is a leading CLM platform that solves your end-to-end contract management issues.  Visit https://www.spotdraft.com to learn more.

What does a former GC-turned-executive recruiter wish she'd known about creating a personal brand, working with search firms, and negotiating the offer? How do executive recruiters help take careers where they need to go—not just to the next level? And when is the right time to start building a meaningful relationship with executive recruiters?Joelle Khoury, consultant at Egon Zehnder, built a towering career as an in-house counsel at private equity giants like Saban Capital Group and Fifth Wall and at law firms including Cooley LLP and Gibson, Dunn & Crutcher LLP. But when the time came to make a change, she pivoted from leading to legal to helping other lawyers find the career paths that best suit their interests.Listen as Joelle shares insider tips on how to reach out to executive recruiters, navigate the interview and offer processes, the wrong way to approach a negotiation, and when to reassess whether the profession you’ve chosen is still the right one for you.Read detailed summary: https://www.spotdraft.com/podcast/episode-45Topics:Introduction: 0:00Building a legal career at Gibson, Dunn & Crutcher and Cooley LLP: 3:09Comparing Saban Capital Group with Fifth Wall: 5:55Advice to lawyers raising capital for the first time: 8:16Leaving Fifth Wall and reassessing your career plan: 9:55Taking time off before joining Egon Zehnder: 11:22Transitioning from a legal career to executive recruiting at Egon Zehnder: 16:07Advice to executives looking to executive recruiters for new opportunities: 21:43Tips for nailing the interview process: 26:10Tips for negotiating after receiving an offer: 29:40Lessons you learned as a recruiter that you wish you’d known as a GC: 33:33What you wish you’d known as a young lawyer: 35:27Connect with us:Joelle Khoury - https://www.linkedin.com/in/joelle-khoury-21959814Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

How can training to be a professional opera singer translate into the legal operations profession? How do you build a career in legal ops without any formal training? And what role should technology play–if any–in a strong legal ops program?Cory Clines, Legal Operations Manager at Campari Group, was able to transfer valuable lessons from his life as a conservatory-trained opera singer into his fifteen-year-long career in legal ops, like the importance of collaboration and the need for a shared vision among teams. In his current role and at former companies like Advance Publications and Lloyd’s, Cory was able to leverage his love of technology into managerial roles that revolutionized legal processes with efficiency-maximizing software.Listen as Cory discusses how to develop strong relationships with tech vendors, building legal ops teams from scratch, earning the trust of your GC, the best ways to run an RFP, and more.Read detailed summary:  https://www.spotdraft.com/podcast/episode-44Topics:Introduction: 0:00Training as an opera singer: 4:01Considering skill transfer from opera to legal operations: 12:12Moving forward by earning the trust of your GC: 14:46Deciding to leverage technology in legal ops: 16:34Running RFPs from an in-house perspective: 18:59Identifying new opportunities to advance your legal ops career: 22:05Advice to legal ops professionals who feel pigeonholed in one aspect of the role: 24:27Considering how curiosity affects your work: 27:23Questioning the need for tech expertise as a legal operations manager: 28:47Looking back at tech implementations that went wrong: 31:20Building a legal ops team from scratch at Campari: 38:14Using tech to drive legal ops process: 41:15Book recommendations: 46:01What you wish you had known when you started in legal ops: 47:58Connect with us:Cory Clines - https://www.linkedin.com/in/corywilliamclines/Tyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.

If you're a foreign-trained lawyer who wants to move to the U.S., how do you find a job? Why should companies look to foreign-trained lawyers in an increasingly globalized world? And how should you navigate moments of big career transitions?Flavia Naves, former general counsel at Circle, relocated to the United States after studying law in her native country of Brazil, and went on to become an authority on law and regulation related to crypto, fintech, digital payments, and much more. In addition to her long lost of leading legal roles, she is also a board member, of counsel at Kunz and Hathaway, and commissioner of the State of Wyoming’s Stable Token Commission.Listen as Flavia shares the challenges she faced as a foreign-trained lawyer, why she advocates for mentorship and specialized training, what it’s like facing unexpected career transitions, and how she came to realize that her biggest differences are her biggest strengths.Read detailed summary:  https://www.spotdraft.com/podcast/episode-43Topics:Introduction: 0:00Moving to the United States after growing up and studying law in Brazil: 2:44Entering the legal job market as a foreign-trained attorney: 3:51Seeking mentorship from other foreign-trained lawyers: 8:18Why companies should consider more foreign-trained attorneys: 11:23Considering LLMs: 14:36Navigating moments of career transition: 18:24Deciding to leave your GC role at Circle: 20:36Life after Circle: 25:38Book recommendations: 31:15What you wish you’d known as a young lawyer: 32:42Connect with us:Flavia Naves - https://www.linkedin.com/in/fnavesTyler Finn - https://www.linkedin.com/in/tylerhfinnSpotDraft - https://www.linkedin.com/company/spotdraftSpotDraft is a leading CLM platform that solves your end-to-end contract management issues. Visit https://www.spotdraft.com to learn more.