Lily Shen of Transfix

    We Spoke to Lily Shen of Transfix on Being an Effective Leader During Turbulent Times

    As part of my series about the “Five Things You Need To Be A Highly Effective Leader During Turbulent Times,” I had the pleasure of interviewing Lily Shen.

    Lily Shen is the CEO & President at Transfix. Under Shen’s leadership, Transfix experienced 300% growth within her first year with the company. Transfix’s best-in-class carrier network is trusted by some of the world’s most recognized brands, including six of the top ten retailers and five of the 10 largest food and beverage brands in America. Prior to joining Transfix, Lily held senior leadership positions at renowned companies such as eBay, Wealthfront and IDEO.

    Our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

    I started my career at Goldman Sachs in the mid-90s. While I loved the rigor, drive, and intellect of the people I worked with, I began to think about career paths that would allow me to take part in building new ideas early on. In 2000, I had a once-in-a-lifetime opportunity to join eBay. This was during a time when online marketplaces such as eBay, Amazon,, and Alibaba were beginning to revolutionize how businesses and consumers purchased goods. Ebay was a Silicon Valley darling: it survived the dot-com crash, was young and profitable, and was going through an important period of innovation and growth. It was there that I developed a deep understanding of the ins and outs of online marketplaces, including the unique challenges of balancing supply and demand, building strong and loyal communities through sticky product features, and the huge opportunities that existed for eCommerce by eliminating market inefficiencies. I experienced firsthand how a strong marketplace can transform how consumers and businesses purchase goods and services — and decided to take this experience to help build other businesses. After eBay, I spent the next decade building companies such as Wealthfront as an early employee and also advising companies such as Mercari, Coupang, and WeChat. It’s been incredibly rewarding to be a part of these companies’ journeys to redefine experiences, business models, and trends in their respective industries and markets.

    I met Drew and Jonathan, the founders of Transfix, during my time at Canvas Ventures. Drew’s firsthand experience in the freight brokerage space, combined with Jonathan’s software development savvy, was inspiring to me. I recognized similar patterns of inefficiency in the logistics industry as I’d seen in other industries. Things such as fragmentation, limited access, lack of transparency, and very little use of data and technology which could unlock the ability to better connect two sides of a marketplace and provide new tools to help shippers and carriers manage their business. The strength of the founders, along with the industry’s characteristics, led me to feel confident that Transfix was going to revolutionize the logistics industry.

    None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful to who helped get you to where you are?

    Many people have truly been part of my own professional and personal journey. I’ve learned from each person who has been a part of my life and at various inflection points throughout my career. I believe it’s important to surround yourself with individuals who have different perspectives, experiences, and strengths — whether the individual is a world-class business leader, a high-potential intern, someone with grit who has worked up through the ranks, or someone who has modeled work-life balance. Keep an open mind about who you can learn from in different, and often unpredictable, ways because inspiration can come from anyone.

    Extensive research suggests that “purpose-driven businesses” are more successful in many areas. When your company started, what was its vision, what was its purpose?

    Transfix was founded to create a simpler, smarter, and more sustainable freight ecosystem. While it may appear that moving freight from point A to point B is “easy”, the reality is that it’s incredibly complex, inefficient, and manual, leading to massive waste. Over 65 billion miles are driven empty each year! These empty miles translate into a negative environmental impact, untapped opportunities and cost savings for shippers, and untapped business potential for thousands of small- to- medium-size trucking companies. Transfix connects reliable freight to capacity in the most optimized manner to increase efficiency, which is a win for shippers, carriers, consumers, and our environment. And I’m honored to lead the charge to achieve this mission.

    Thank you for all that. Let’s now turn to the main focus of our discussion. Can you share with our readers a story from your own experience about how you lead your team during uncertain or difficult times?

    I became CEO of Transfix in March and three days later, I led an immediate transition of the company’s operations and engineering team from the office to working from home due to COVID-19. During difficult times, it’s critical to lean into your people and your customers — this is when leadership matters the most. What you do (and do not do) has a direct impact on your employee experience and shapes your company culture. It’s also a critical moment to be there for your customers. They need to know that you are there for them and will continue to invest in the business and products that they rely on as a trusted partner for the long haul. At the end of the day, there will always be bumps in the road. In those moments, you need to acknowledge the tough times, but also ensure that everyone sees the opportunities that always lie ahead no matter the circumstance.

    Did you ever consider giving up? Where did you get the motivation to continue through your challenges? What sustains your drive?

    I have lived through moments where I felt close to defeat. I believe everyone has! Two things have always helped me through these periods: 1) reframing the situation to focus on the opportunity, learning, and personal growth at hand, and 2) my dedication to the people around me. Reframing can lead to new and exciting possibilities you would not have otherwise thought of, which can be energizing. Equally important to me is focusing on the people around me and how I can help them be successful. I draw tremendous strength from thinking about the impact I can have on others.

    What would you say is the most critical role of a leader during challenging times?

    It is important for leaders to lead by example at all times, but certainly the most challenging times. Leaders need to get in the trenches and get their hands dirty with their team. Working side-by-side with your team will show them that you hold yourself accountable to the same standards you hold them to, and that you see, acknowledge, and appreciate the hard work they put in. It’s also important to be human. This means having empathy for others and also sharing moments of vulnerability you are experiencing as a leader. This openness will build mutual respect, understanding, and trust. Lastly, leaders always need to ensure they provide their teams with a clear North Star. A clear vision will inspire the team to get through difficult or uncertain periods.

    When the future seems so uncertain, what is the best way to boost morale? What can a leader do to inspire, motivate and engage their team?

    The primary way leaders can inspire, motivate, and boost the morale of their team is by developing and communicating a clear vision for the future, and then working to create a deep connection between the team and that vision. A team that is driven by purpose will feel more closely connected to each other, draw greater satisfaction from work, and feel inspired by their day-to-day. I also believe that transparency of information goes a long way. Transparency will build a culture of trust, authenticity, and high performance (as people will be operating with the right information and context). Lastly, showing your team you appreciate their hard work and dedication helps employees rally through uncertainty. Periods of high stress can wear down even the most dedicated and energetic employees, so it is important to constantly acknowledge people’s efforts, sacrifices, and personal challenges.

    What is the best way to communicate difficult news to one’s team and customers?

    No matter what the news is, it must be delivered with authenticity, integrity, and respect. Sometimes leaders avoid hard conversations, but navigating these moments with grace can actually build trust. Make sure your team understands the context behind a decision. The information, thinking, and process that resulted in a thoughtful decision can help folks come to terms with the news you are delivering. I also think it’s equally important to invite dialogue and to clearly articulate the path forward. Communicating difficult news can be one of the hardest jobs as a leader. There will be ups and downs, but how you move forward is key.

    How can a leader make plans when the future is so unpredictable?

    Firstly, a leader must know when and where to take risks. While no one can predict the future, any leader worth their salt can recognize and plan for potential risks by evaluating a range of scenarios based on the information in front of them. A rapidly changing environment is often fertile ground for developing transformative strategies, and you should maintain a healthy appetite for risk to take advantage of any opportunities that may arise. Secondly, a leader must balance building short-term and long-term value. Often leaders focus just on what’s right in front of them, but you also have to think about the long term to ensure the greatest success to customers, employees, and investors. At the end of the day, companies exist to create lasting value for their constituencies, so don’t be myopic with your planning or decision-making.

    Is there a “number one principle” that can help guide a company through the ups and downs of turbulent times?

    Be biased towards action. When times are turbulent and uncertain, it’s easy to retreat, which is a common mistake. Mobilize your teams to come together even more, identify new opportunities, proactively plan, and make conscious decisions. A decision may mean new or different initiatives — or simply staying the course.

    Can you share 3 or 4 of the most common mistakes you have seen other businesses make during difficult times? What should one keep in mind to avoid that?

    During difficult times, I believe there are four keys to success:

    Investing in your people. They are the engine that drives you forward. Setting them up for success will set your company up for success.

    Making thoughtful (but quick) decisions. Don’t be afraid to make big decisions, even with imperfect information. The opportunity cost of not deciding is likely greater than the cost of making a wrong decision you can course correct for later.

    Planning ahead. Don’t get bogged down on day-to-day crisis management. Take the time to plan out and identify changes or resets where needed.

    Being transparent. Treat your employees with the respect they deserve. Provide them with the context and information they need to both execute the agenda successfully, and also feel confident about the future.

    Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

    Growth and innovation is a never-ending cycle that rotates from opportunity identification to prioritization, to measurement, to decision-making. I spend time thinking about what my team should and should not be doing. Concentrating limited resources on the few major levers that will have transformational impact on the business requires a continuous effort to remove distractions (e.g. unsuccessful or modestly successful projects) from the company agenda. Once I’ve decided on what our key bets are, I take a very data-centric approach in my day-to-day management. This ensures you’re asking the right questions and collectively making the highest impact decisions.

    Here is the primary question of our discussion. Based on your experience and success, what are the five most important things a business leader should do to lead effectively during uncertain and turbulent times? Please share a story or an example for each.

    There are five core things a leader should do to lead effectively during uncertain times:

    [Re]share your vision. A clear North Star will align and rally your organization around a common goal and help you and your team streamline decisions and prioritizations. Continuously remind your team of this vision, especially when times are tough.

    Lead by example. Be the leader you wish you had when you were starting your career, and others will follow. To me, that means focusing on not just what is achieved, but how you and your teams get there.

    Have a bias towards action. Your sense of urgency will set the tone for the broader organization. Prioritize, make impactful decisions, and iterate every single day. Don’t fear mistakes. Instead, focus on continuous learning.

    Be transparent. Transparency is empowering. It gives people important context that can help guide good decision-making across the company. When times are tough, it helps alleviate some of the uncertainty your team feels about the future and ensures they remain connected to the vision.

    Show appreciation. Make the time to meet with employees one-on-one, celebrate wins wholeheartedly, and acknowledge challenges they may be experiencing. Ultimately, businesses thrive or die because of their people, so taking care of your people is a must.

    Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

    “Failure isn’t fatal, and success isn’t final.” Just like an athlete, sometimes you will be at the top of your game, and sometimes you will live through a painful losing streak. When you are winning, stay humble and don’t take your successes for granted — and when you are losing, stay positive. You will be surprised at how far expecting future success will take you. Throughout these ups and downs, don’t forget to celebrate your small and big wins, recognize and apply learnings from any mistakes you’ve made, and thank people who have helped you along the way.

    How can our readers further follow your work?