Meet Allison Amadia, a seasoned executive with over three decades of leadership and successful management in the technology space. Her expertise spans financial services, technology, e-commerce, and payments, making her a trusted advisor for both public and private technology companies. With a multifaceted skill set, Allison provides invaluable insights to technology companies and their executives and boards, on business strategy, operational efficiencies, security, regulatory compliance, executive compensation, commercial matters, and more. 

Allison’s career path has been significantly shaped by her appreciation for the dynamic and innovative nature of the tech industry. Drawn to its rapid changes and constant evolution, she found the disruptive potential of technology particularly appealing. Her journey into the world of FinTech, spanning nearly a decade, was driven by her recognition of its capacity to revolutionize innovation in the current era. Allison is deeply committed to empowering consumers to take charge of their financial lives, and this philosophy resonates strongly with Titan’s mission: to bring financial literacy to the everyday investor and access to investment options that would otherwise be unavailable in an engaging and delightful way. This commitment is evident in the recent launch of Titan’s innovative product, Smart Cash¹, which simplifies cash-like investment opportunities for maximum anticipated after-tax returns. 

With a rich background in the tech and FinTech realms, Allison approaches her work with a focus on business strategy and a deep consideration for consumer needs. She operates as a thoughtful investigator, delving beyond the “how” to uncover the “why” and the “so what.” This approach extends to her teams, cultivating an understanding of business goals and client viewpoints. This comprehensive perspective guides her legal counsel, ensuring the well-being and education of her business partners and clients. Despite the fast-paced nature of her work, Allison has always prioritized the mentorship and professional growth of her team. The relationships she has developed with the people she counsels and mentors has been a highlight that has significantly enriched her professional path.  

Here we present highlights from the interview that showcases Allison Amadia’s remarkable journey and extensive experience in the tech sector  

How do you balance providing legal guidance with fostering innovation and growth within these companies? 

It is always a balance, to be sure. But it is a bit like a puzzle; once you solve it, it is very gratifying. One of the reasons I left law firm life was because I wanted to get closer to the companies I represented and understand the business context. By embracing business goals, lawyers and compliance professionals can not only provide better counsel that fosters innovation and growth, but they can also provide business input that accomplishes the same. Start-ups are all about owner mentality, where everyone thinks and acts like an owner of the business. Legal and compliance professionals are no different and should do the same. But there is a line that mustn’t be crossed. One could argue that this is an ethical or moral line. No matter what you call it, it also makes smart business sense, so I don’t see the two at odds. In other words, doing the right thing by your client, or doing the legal or regulatory thing, shouldn’t be viewed as at odds with innovation. There are countless examples of businesses who viewed following rules and innovation as a zero-sum game, and they aren’t around today because of it. I prefer to think of it as sustainable innovation out of a profound respect for rules and regulatory structures that are fundamentally in place to protect against overreaching. 

Can you describe a complex business strategy or operational challenge you’ve assisted a technology company with, showcasing your creative problem-solving approach and its outcomes? 

Frankly, every day presents complexity and operational challenges that require thoughtfulness and a strategic perspective. Over my career, there have been widely known industry challenges like Y2K (for those that may remember) or, more recently, the collapse of SVB.  But there are always lesser-known, more company-specific strategic or operational challenges that need to be tackled head-on. While I can’t describe any one of these specifically for obvious reasons, my approach to these quagmires is often the same: assemble the right team; figure out what you know and what you don’t know (what is the threat or opportunity); figure out how to get the information you don’t know so you are operating from a position of full information; understand the big picture (what is the outcome that is desired and the consequences of not achieving it); figure out what the other side wants (or their perspective); and finally work as a team to drive the best possible outcome for both sides. If there is “creativity” that is part of this exercise, it is really a steadfast belief that “no” is an answer of last resort. One of the reasons I chose not to be a litigator is that I believe that smart, strategic business lawyers are more often looking for a win-win for all parties involved. That doesn’t mean compromising—just more appreciation for the needs and interests of a regulator, vendor, client, or other counterparty. 

How do you approach integrating DE&I principles into legal and compliance strategies, and what impact have you observed as a result? 

I have managed HR for several of my companies in addition to managing legal and compliance. I have also had the opportunity to co-chair a DE&I committee for a company as an executive lead. These experiences have helped me develop my view on the importance of DE&I at any company. 

DE&I, from a legal and compliance standpoint, are table stakes. I think most companies today try to hire, manage, and exit employees in a legal and compliant manner. I certainly only work for those that do. 

But DE&I is really a business strategy—a labor, recruitment, and retention strategy, to be specific. Beyond legalities, hiring a diverse set of talent and retaining that diversity has been proven to lead to happier, more loyal employees who work harder and make better decisions, enabling their DE&I-rich companies to have better outcomes.

So how does one build a strong DE&I culture? I think it has to be grass-roots work, but it starts with creating a space where employees feel like they have a voice and are heard. And that voice then creates a flywheel that attracts individuals to the organization who also value DE&I.  

How do you cultivate strong business partnerships while maintaining a focus on ethics and integrity, especially in industries as dynamic as technology and finance? 

I believe strong business partnerships are even stronger with a focus on ethics and integrity, not weakened by them. In today’s complex, interwoven business environment, a company is only as strong as its partners. Companies rely on their partners as an integral part of their compliance program, and likewise, their partners rely on them for the same. Any weak link in the chain is risky for all related entities and, more importantly, for their customers. Take Titan’s business, for example. We rely on our custodian to safeguard our clients’ funds for most of our strategies. If they do not act ethically and with integrity, that failure reflects directly on us.   

I have also learned that in contract negotiations with partners, hiding the ball leads to a bad partnership that eventually falls apart. The interests of the parties truly need to be aligned for business partnerships to be successful. Another business reason to act ethically and with integrity in business partnerships. TL;DR: Cultivating ethics and integrity in and with business partnerships is just good business, leaving aside the ethical reasons for doing it.   

Being named one of the Top 25 Women Leaders in Financial Technology and a finalist for General Counsel of the Year are notable achievements. How do these recognitions inspire you to continue your impactful work in the legal and compliance realm? 

To be honest, I’m not inspired by recognition by institutions or industry peers. I’m inspired by people. At Titan, I get to work with a company filled with super smart whiz kids who are highly motivated to democratize investing to help their generation make smarter, more impactful investment decisions. These colleagues motivate me. The founders of Titan, Joe, Clay, and Max, likewise motivate me. They are truly inspiring by their vision, knowledge, and genuine desire to turn an old, stodgy industry on its head for the betterment of their generation. And finally, my team at Titan inspires me. They are so interested in learning and supporting the company’s needs. They humble me every day by expressing their appreciation for my management style and mentorship. No award can do that! 

What strategies do you employ to continuously stay at the forefront of legal and compliance developments within the ever-evolving landscape of technology, e-commerce, and financial services? 

I do a lot of reading. I am also fortunate to be a member of the Women’s General Counsel Network, where I get regular updates on issues and challenges facing my peers.  I also have a fantastic network that I have developed over the years. Finally, I make sure I am surrounded by strong outside counsel like Lowenstein Sandler, our corporate counsel, in the areas where we need to know the ever-evolving landscape as it evolves in real time. 

Balancing a strong work ethic with personal well-being can be demanding. How do you manage to maintain this balance, and what advice would you offer to fellow professionals striving to achieve the same equilibrium? 

For me, this question epitomizes my greatest work challenge: work-life balance. I find balance challenging because I truly love my work and find it immensely fulfilling. So, like a good book, I find work hard to put down. As much as this has been a career-long struggle for me, I have learned that continuously working on work-life balance is a struggle worth fighting. Not without compromise and setbacks, but with absolutely no regrets, I have thrived in my career while raising two amazing kids with the love and support of my husband, also a career executive. I am an avid exerciser—mostly tennis but also biking, hiking, and the occasional regrettable run that I didn’t properly train for. 

My advice is nothing great comes easy.  If you also struggle with balance, keep up the good fight!  And believe that you can do it all.  Because you can – but not if you don’t believe it.  Surround yourself with a strong support system.  In all of our 23 years of marriage to date, my husband and I were fortunate to have parents around and willing to help out as needed with kids and dog sitting, enabling us to recharge from time to time. And we are fortunate to have really good kids who have made parenting look easier than it is – but that’s just luck. I have always had amazing managers who understand that family and health are right up there with work and are not secondary. If that doesn’t describe your manager, then get a new job. Life truly is too short. 

Your journey and contributions as a Chief Legal and Compliance Officer are truly inspiring. Looking ahead, what legacy or impact do you aim to leave within the realms of legal leadership, technology, and financial services? 

I’m not ready to write this chapter. Meaning I am not ready to think about my legacy as, hopefully, I still have more years ahead to continue to make an impact. However, one hallmark of my life’s work thus far is that I have met, worked with, and befriended many amazing colleagues along the journey and am still in close contact with most of them today. That’s not always easy for a general counsel and chief compliance officer to accomplish, just due to the role itself. My belief is that approaching work as part of life and truly getting to know the people you work with on a personal level brings greater satisfaction to you and those around you. I’m not sure that makes a legacy, but perhaps it is a valuable lesson. 

And then there’s mentorship. I am immensely grateful for my opportunity to mentor many amazing individuals over the decades. For those who have worked for me, they know my unwavering commitment to supporting their development at every opportunity. I take mentorship seriously. It is ingrained in my persona and well seeded from my experience as a professor or visiting lecturer for several years at Santa Clara Law School. There is nothing more satisfying than seeing that light bulb “turn on” for a student or employee and knowing that I played a part in helping them learn something new or approach a challenge differently. Mentoring and teaching others is not an extra in the way I approach my job; it is my job. And, if I had to guess, it will likely be my legacy. 

¹ Smart Cash strives for tax optimization. Please note that after-tax yields are calculations, and actual outcomes may vary. This content is provided for informational purposes only and should not be considered as investment or tax advice. All investments involve risks. View risks and disclosures at titan.com/smart-cash-disclosures. 

The views and opinions expressed in this article are those of Ms. Amadia, and do not necessarily reflect those of Titan Global Capital Management, Inc. (“Titan”). A portion of the costs of production for this article was subsidized by Titan.   

Please visit: https://www.titan.com/legal