Invest the Time in People: Interview with Alibaba's John Caplan

John Caplan_Headshot.jpg

I recently went one on one with John Caplan. John is the President of North America & Europe for Alibaba.com and previously served as Global CMO. John was the founder and CEO of OpenSky, which was acquired by Alibaba and was the CEO of Ford Models.

Adam: Thanks again for taking the time to share your advice. First things first, though, I am sure readers would love to learn more about you. How did you get here? What experiences, failures, setbacks or challenges have been most instrumental to your growth?

John: The things that I care the most about are my family and helping businesses scale. I’ve spent my professional life building companies like Starbucks Coffee, Arizona Iced Tea, About.com and OpenSky. I’ve also been building the vision and operating plan for transforming Alibaba.com into the world’s most dynamic B2B marketplace. For context, we do tens of billions of GMV and are one of the fastest growing revenue business at Alibaba Group, with more than 50% YoY revenue increase. 

Our mission at Alibaba.com (and really my personal / professional life mission) is helping small businesses entrepreneurs, marginalized business builders and companies who have 500 or fewer employees. We are providing them with the tools, technology, information and opportunity to grow a profitable, sustainable and meaningful businesses. 

Through our global B2B ecommerce platform, we’re making it easy for small businesses globally to do business with one another.

I come from a family of entrepreneurs, and in the 1900s my grandfather and his siblings started a jewelry business, Oscar Heyman & Brothers, that is still thriving today. As I was growing up, I learned about having a customer-first mindset, being a team player, and having the grit and resilience to succeed.

Before joining Alibaba.com as the President of North America and Europe and Global CMO, I started OpenSky, an ecommerce platform that used technology to unlock the growth opportunity of small businesses. Before OpenSky, I was the CEO at Ford Models, one of the largest and most successful global fashion talent firms, with operations in 50 countries and across every aspect of the talent industry. I also previously served as the CMO and President of About.com and helped pioneer the engagement of content on the Internet.

Throughout my career, I’ve always made sure that I center myself on what’s important, both professionally and personally, but I also think the following each morning, “How can I earn the trust of our team, customers, and partners?” Having clarity on my priorities allows each day to be more productive and enables me to learn something new that can help our customers. 

Adam: In your experience, what are the key steps to growing and scaling your business?

John: The key areas to growing and scaling our business have been staying true to our values and our mission while being nimble about the how we build our tools to support our customers. The allocation of capital and time are establishing data-driven ways to achieve this. Otherwise, it’s just a lot individuals sharing opinions. To scale, data, customer understanding, creativity, courage and luck are required. 

Since the Covid-19 pandemic, we saw nearly two decades of change take place as businesses realized getting digital is no longer a nice-to-have, but a must-have to bridge from surviving to thriving in the next era of business.

Adam: What is your best advice on building, leading and managing teams?

John: Hire smart, creative and hungry people.

Give them every ounce of your loyalty and energy and ask them to solve the needs of customers. 

Trust them completely. At Alibaba.com we like to say, “trust makes everything simple” and this is certainly a great way to build – if you have trust, everything else flows from there. 

At OpenSky, we would have ice cream parties to celebrate our failures and tequila shots for successes. Everyone makes mistakes. And everyone can get on base. The most important thing is to get the right group of people together - laugh at yourself, have fun, enjoy the adventure and never ever give up. 

I’ve found that hiring thrill seeking entrepreneurs enjoy the chaos and focus on customers. 

Leaders must also care about the people they work with, as being a strong and reliable manager is about leading with empathy and being aware of your impact on your team members’ success. Managers should meet weekly or bi-weekly with their employees to discuss progress, goals and any issues that arise. It’s important for leaders to guide their team in the discussion by asking, “What are your obstacles? What are the objectives and key results (OKRs)? What help do you need?” If leaders are asking these questions, it’s just as important to be listening to the answers to take the necessary steps to help employees achieve both their goals and the company’s goals. 

Adam: What are three things everyone should understand about marketing?

John:

  1. Marketing is fun!

  2. Great brands have a point of view.

  3. Loved brands care and act to benefit their communities and live their values (for example, Airbnb is brilliantly housing 20k Afghanistan immigrants).

Adam: What are three things people who work in marketing should understand?

John: Content, community and commerce are all now inextricable linked together.  

A marketer/CEO is conducting an orchestra – pulling the customer, the functional business areas, the team, the ecosystem of partners and competitors – all of these feed into the content, community and ultimately the P&l. The team at Assembly (Helium10) have done this in an impressive way, with 500k small-and-medium-sized businesses (SMBs) coming together to use tools and the community to create self-sustaining businesses.

Adam: In your experience, what are the defining qualities of an effective leader? How can leaders and aspiring leaders take their leadership skills to the next level?

John: The defining qualities of an effective leader include the ability to listen, to change, to adapt when necessary and to hold the line. This judgement is the role of leadership.

Leaders have the responsibility to create a work environment that is supportive, challenging and transparent.

What truly drives passion and hard work from employees is trust and teamwork, and in turn, creates enthusiasm to help a business and its customers succeed. 

Adam: What are your three best tips applicable to entrepreneurs, executives and civic leaders?

John: Entrepreneurs and leaders must focus on building a team who are diverse, creative and who have the grit to make an impact. Once the team is in place, ensure that you are constantly tracking and measuring OKRs. I’ve learned that if something cannot be tracked, then you shouldn’t do it.

Also, as an everyday practice and mentality, customers come first. No matter the industry you’re in, it’s crucial to listen to the wants and needs of your customer, and if they say something isn’t working, trust them and don’t be afraid to pivot.

Adam: What are the best lessons you have learned from your corporate board work? What advice do you have for fellow board directors and for those who aspire to serve on corporate boards?

John: I love the board work that I do. It’s exciting – the companies are run by brilliant teams and most all I find it helpful to learn how other leaders are tackling all the changes in the economy. 

From my experience, I’ve learned how powerful it is to have a Board that has an appetite to get things done. This in turn will inspire others, as I, personally, work best when I’m surrounded by a team who is just as motivated and dedicated.

Adam: What is the single best piece of advice you have ever received?

John: The best advice I’ve ever received is to not stop believing. This goes with my favorite quote, “If the sun and moon should doubt, they’d go out.” This quote furthers the idea that you must have faith in a mission or goal, but at the same time, you must put in the hard work to achieve it.

Another quote I like is, “Learn the rules like a pro, so you can break them like an artist.” Picasso said that and I think it applies to the idea that great masters stand on the shoulders of the giants that came before – the more you can understand their thinking, the more likely you can create inspiring work today. 

Adam: Is there anything else you would like to share? 

John: To be a good leader, invest the time in people. We live in a more digital world than ever before, but it’s important leaders and managers take the time to show empathy to their employees and help them grow in their careers. That’s what differentiates an average leader from the rest.


Adam Mendler is the CEO of The Veloz Group, where he co-founded and oversees ventures across a wide variety of industries. Adam is also the creator and host of the business and leadership podcast Thirty Minute Mentors, where he goes one on one with America's most successful people - Fortune 500 CEOs, founders of household name companies, Hall of Fame and Olympic gold medal winning athletes, political and military leaders - for intimate half-hour conversations each week. Adam has written extensively on leadership, management, entrepreneurship, marketing and sales, having authored over 70 articles published in major media outlets including Forbes, Inc. and HuffPost, and has conducted more than 500 one on one interviews with America’s top leaders through his collective media projects. A top leadership speaker, Adam draws upon his insights building and leading businesses and interviewing hundreds of America's top leaders as a top keynote speaker to businesses, universities and non-profit organizations.

Follow Adam on Instagram and Twitter at @adammendler and listen and subscribe to Thirty Minute Mentors on your favorite podcasting app.

Adam Mendler