Introduction: 00:00

• In this episode of The Abstract, Tyler Finn interviews Gary Spiegel, former SVP and General Counsel at Anaplan. The podcast delves into Gary's early career and highlights his achievements as a legal leader in the industry.

Gary’s start with regulatory law and shift to the business side: 01:32

• Gary had a unique career start at the Federal Reserve Bank.
• His shift from the regulatory environment to the fast-paced tech world in Silicon Valley. 

The journey from MySQL to Sun Microsystems to Oracle through multiple acquisitions: 06:58

• Shifting from a stable company like Adobe to MySQL to pursue growth opportunities like participating in an IPO.
• Essentially being part of the sales team as a lawyer at MySQL.
• Fostering unity, encouraging open discussions and collaboration within the team.
• Learning from uncertainty and business ups and downs, and being part of transformative events in companies’ history.

Supporting a company as its first GC and taking over the legal function from the CFO: 15:54

• Career progression from the role as a cloud attorney at LiveOps to first legal hire at Anaplan.
• Importance of personal connections leading to new job opportunities.
• Growing the legal function at Anaplan, from a single hire to a team of 20.
• Communicating Legal’s value in a start-up environment.

The right time to join a company as the first legal hire or GC: 22:22

• Evaluating one’s own career trajectory, goals, skills, and interests and aligning that with the company's needs and stage of growth.
• Choosing from a spectrum of roles for legal leaders, ranging from being an executive strategic advisor to a hands-on contract closer, to determine one's own fit.
• Coaching the leadership team, especially when it comes to start-ups, about what Legal’s role should look like in a company.

Behind the scenes to Anaplan's successful IPO: 27:18

• Motivation, dedication, and preparation are required to achieve a significant milestone like an IPO.
• What the prep stage looks like before planning an IPO, and where legal fits in.
• The importance of understanding the business and building strong relationships with key individuals and executives to ensure successful transactions.
• Having a project management mentality in your approach to IPO planning.

Thoma Bravo's acquisition of Anaplan and Legal’s role in ensuring success: 33:50

• Navigating take-private transactions and acquisitions, and the strategic thought that goes into it.
• Shifting focus from mass public investors to a single buyer.
• Secure the best deal for the company and investors through an accurate depiction of the company and comprehensive due diligence.
• Thinking about life after the transaction, once the previous investors are out of the picture.

Building a team of 20+ people and setting them up for success: 37:18

• Gary’s initial focus was on relieving his workload and addressing specific needs within the organization – “keeping himself sane”, as he puts it.
• When to hire flexible, multipurpose players who can react quickly to unknown scenarios vs people with specific skill sets.
• Building a strong culture around closeness, learning, and growth.
• The difference between hiring for public vs private companies.

Communicating the value of legal within the business: 43:00

• Nailing traditional legal work to build key relationships, then addressing the business's strategic needs and gaps.
• Taking on expanded roles such as compliance, HR, ESG, corporate governance, etc.
• Connecting different aspects of the organization through superpowers unique to lawyers, such as attorney-client privilege.
• Measuring the intangible aspects of Legal through relationship-building.

Leveraging legal expertise as a springboard into other roles: 49:18

• Fostering a culture of support and investing in the professional development of your team.
• Bringing your expertise into something adjacent.
• Seeking opportunities for cross-functional collaboration to align individual aspirations with corporate needs.

Strategies for managing stakeholder relationships and balancing legal support: 52:00

• Striking a balance between providing legal support vs handholding to ensure efficiency, using rules of engagement and service level agreements.
• Understanding business needs and differentiating where you need to act as a connective tissue vs take a step back.
• Being open to discussions at the executive level.

The future of in-house legal roles: 56:56

• The opportunity to extend beyond traditional legal work into strategic leadership positions through functional literacy.
• Balancing the expansion into other functions depends on individual career goals and the trust built within the organization.
• What’s next for Gary?