Harvard in Tech
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Harvard in Tech

Harvard in Tech Spotlight: David Lessing, COO of Ray Dalio’s Family Office and Senior Advisor to and Former CRO of Addepar

David Lessing, COO of Ray Dalio’s Family Office

I spoke with David Lessing, new Chief Operating Officer of Ray Dalio’s family office and Senior Advisor to and former Chief Revenue Officer of Addepar.

David was a lawyer by training, having attended Harvard Law School after Harvard College. He joined McKinsey to transition from law into business, and there, he worked closely with many wealth management firms on strategic projects. He then moved into operating roles in wealth management, first at Merrill Lynch where he was Head of the Global Private Client Direct Division and later at Morgan Stanley, where he led the firm’s integration with Smith Barney and served as Chief Operating Officer of the U.S. Wealth Management Group.

Having spent most of his career at large institutions, David sought to do more entrepreneurial work, so he spent the past 7 years in the fintech world, working with startups in advisory, CEO, and most recently, CRO capacities.

David shared his advice for cultivating strong partnerships, developing deep customer understanding, and building trust.

Sell with empathy. Actively restrain yourself from diving immediately into the sales pitch. Instead, spend time in discovery, understanding the prospect and identifying where they have gaps or challenges in their work flow. Then, tailor your communication with empathy powered by this deeper understanding of each prospect’s unique situation.

Be service-oriented. Regardless of how new you actually are to the sales role or the company, make prospects feel like you are seasoned through following a structured, yet tailored process. Instead of solely focusing on the solution and technology itself, guide them along the end-to-end journey from discovery to implementation to support and beyond. Make them feel seen, heard, and taken care of each step of the way to instill greater confidence in your product and company.

Ask the right questions. Manifest your deep understanding of your client and their industry through asking thoughtful questions (a great read David recommends on this topic is this piece on 9 non obvious ways to have deeper conversations). By demonstrating your knowledge of their space and especially of the challenges they face, you empower the other party to open up, share more, and engage further.

Operate at the lowest level of detail. Every piece of your company’s presence reinforces your brand — from having the right advisors to making the right hires to having high quality proof of concepts with the right players to publishing the right thought leadership in the right publications. Especially in an industry with fintech where trust building and differentiation relative to incumbents is so important and challenging, these seemingly small details can collectively make all the difference in establishing the necessary credibility with your audience.

Take the time to understand people’s superpowers. An important part of leadership is finding people’s talents and integrating them in roles that best leverage their strengths. Many times, these talents are not obvious at first glance, but understanding them and utilizing them are crucial to the success of any leader and team.

Always know there is more to learn. One of David’s favorite quotes is from Ray Dalio: “”If you don’t look back at yourself and think, ‘Wow, how stupid I was a year ago,’ then you must not have learned much in the last year.” You don’t know as much as you think, and it is important to always keep an open mind and be driven by your curiosity.

Find people who give you feedback. Throughout his career, David has had great team members, managers, and mentors to give him feedback on his areas for growth so that he could better target his focus and experience to assemble a diverse array of skill sets which led to his later involvement in a wide range of leadership roles from advising to COO to CRO.

Take advantage of setbacks. Much of life is luck and chance. Don’t lose your humility in times of triumph but also don’t take challenges too much to heart. Just like “buying the dip” in the stock market can yield great returns, leveraging obstacles as an opportunity for growth can yield incredible career and life outcomes.

Looking ahead, David is excited to now join the Dalio Family Office as COO where he will have the opportunity to work with a strong team to continue building an enduring multigenerational institution with significant philanthropic impact on issues such as public education, environmental protection and global access to technology.

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