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Women of the C-Suite: “What defines you at your core will inform how you show up and make decisions for the entire team,” With Anu Gupta of Jyve

Today I had the pleasure of interviewing Anu Gupta. Anu is COO of Jyve, the leading platform for in-store flexible and skilled labor. Anu has over 20 years of experience in driving P/L results across diverse retail, technology and private equity organizations. Prior to Jyve, she was Senior Vice President of Strategy Execution and Operational Excellence […]


Today I had the pleasure of interviewing Anu Gupta. Anu is COO of Jyve, the leading platform for in-store flexible and skilled labor. Anu has over 20 years of experience in driving P/L results across diverse retail, technology and private equity organizations. Prior to Jyve, she was Senior Vice President of Strategy Execution and Operational Excellence at Target. Prior to that, Anu also served as a senior executive at Hellman, and Friedman, Michaels, Safeway and HCL Technologies. She has a proven ability to drive changes, turnarounds and operational transformations; to raise and invest capital, and to build, lead and manage teams.


Can you tell us a story about what brought you to this specific career path?

I love to move things from point A to point B as a way to problem solve. I’ve spent the last 20 years working in retail, driving transformations big and small. I’m inspired by the business transformation in retail, but really it’s the diversity of customers that drew me to the work. I believe in alternate voices and points of view, and I’m lucky enough to experience that with our Jyvers.

After helping big retailers like Safeway and Target drive functional change, I was eager to take my skills to a startup I really believed in — that’s why I decided to join Jyve. It’s been fun to help their team strategize ways to meet both financial, social, and business execution needs by matching skilled individuals (our Jyvers) with tasks that need to get done.

Can you share the most interesting story that happened to you since you began leading your company?

I’ll never forget when I learned about one of our Jyvers named Shelly. She works so efficiently stocking shelves, re-ordering products and merchandising displays for Jyve that she was able to save her earnings for a bit and put it towards a car. She even got a custom license plate for her new car that reads, “I Jyve.”

But the amazing part of the story is how her passion for what she does shines through in all facets of her life. While at the auto dealership, Shelly struck up a conversation with Tammy, her sales rep. Tammy says that Shelly’s enthusiasm for Jyve was overflowing and so infectious she decided to join Jyve not long after. She left her job at the dealership knowing there was an opportunity at Jyve for her to be more passionate about her work.

It’s clear Jyve is completely transforming lives, and it’s been extremely rewarding to witness!

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Looking back at my career, it’s funny how hard I used to be on myself. As a parent and full-time executive, there were many days when I tried to “do it all,” but would end the day feeling like I could have done more for my work or for my family. Over time, I’ve learned that life and work are a continuum, and that balance is achieved moment by moment. Some days you can’t do it all, and that’s ok as long as you’re striving to give your best.

What do you think makes your company stand out? Can you share a story?

Jyve is unique from both a Jyver and customer perspective. We’re making a dramatic impact in handling the staffing issues retailers face by matching skilled talent to unmet in-store needs. Because of this, our platform is mitigating the impact of the retail industry’s high turnover rates. But what makes us really special is that we’re thinking beyond the in-store projects that need to get done — we’re also focused on the people doing the work, Jyvers.

We really want to ensure Jyvers are not locked into a single role, as we see with ride sharing and similar gig work, so we certify our Jyvers to tackle a variety of in-store tasks. Our Jyvers engage their full, diverse skill sets by getting connected to work that they’re uniquely trained for and capable of doing. Jyvers can earn more as the skill required for tasks increases, incentivizing them to complete additional certification.

What’s more, because we have relationships with both CPG brands and retailers, people fluidly find work from multiple avenues to minimize downtime between tasks, so we’re maximizing Jyver’s hours and pay.

Finally, Jyvers have mobility, which means they can grow their skills through new training, have the ability to become Jyve “Gurus” to train new Jyvers, and even grow beyond Jyving. We have former Jyvers working in our HQ full time and have also seen and encourage our customers to pull Jyvers in-house. This is highly unique in the industry and is something we’re incredibly proud of.

Are you working on any exciting new projects now? How do you think that will help people?

We’re always working on exciting projects at Jyve, and we’re excited by our traction so far. To date, we’ve done over $400M in bookings and raised $35M in funding. Currently we have 6,000 Jyvers who have completed 365,000 jobs across 1,200 cities, and the platform is only growing.

In the next few months, we’re focused on building more partnerships with top retail and CPG brands. We will continue to design our projects to change the lives of those in the Skill Economy, giving them flexible and predictable ways to make money and utilize their full skills.

What advice would you give to other female leaders to help their team to thrive?

I expect my team at Jyve to put 110% into everything they do… and I know it’s my job to model that. The world is never going to hand you anything, and those who believe it will never succeed. That’s why I believe in working hard and remaining optimistic. It’s up to you to focus on what you want to achieve and do what you can to make it happen. Although there are some things in business and in life that you won’t be able to control, you can always control the amount of effort you put in.

What advice would you give to other female leaders about the best way to manage a large team?

Stay true to yourself. What defines you at your core will inform how you show up and make decisions for the entire team. As a leader, you also need to have a consumer mindset. There are two ways to anticipate what consumers want and how to best meet those needs — you can guess, or you can build a diverse team that reflects the diversity of your consumers. Always listen courageously to your team and get comfortable being uncomfortable.

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

I learned my work ethic and values from my parents. They raised us to become emotionally strong, financially independent and self-motivated individuals, teaching us not to settle for less My parents gave me all the tools I needed to keep me going all the way, and for that, I am extremely grateful. Thank you, Ma and Pa!

How have you used your success to bring goodness to the world?

My mission is to use what we’re building at Jyve — the Skill Economy — to create social value and catalyze a whole new way of working by creating a system in which employers connect workers with the opportunity to gain new skills to further their careers. I believe people should be valued for their hard work and have the resources they need to succeed, regardless of the various factors that could be holding them back. I’d like to see this idea develop into an ecosystem that is transferable across other industries.

What are your “5 Things I Wish Someone Told Me Before I Started” and why?

1 — Always sit at the table. It can be easy sometimes to discount your own worth, but don’t forget that you’ve earned your spot at the table through your own hard work and perseverance and it’s your responsibility to use it wisely.

2 — Have an informed opinion. Never stop learning so that you can form your own attitudes and beliefs. Be open when others challenge your opinion, but also have research to back your own up.

3 — Get comfortable being uncomfortable. I believe that being uncomfortable is a sign of growth, so if you’re not uncomfortable you aren’t growing.

4 — Respect experience. Value innovation. You shouldn’t discount the things that led you to your mistakes and successes, but don’t let past experiences keep you from taking risks and trying something new.

5 — The race goes to those who persevere. In life and in business you’re going to encounter obstacles, but giving up won’t get you to the finish line.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I’d ultimately like to redefine the future of work by replacing the gig economy with the Skill Economy. I believe that technology changes how we experience humanity, so I’d like to continue to work with Jyve to create technology that enables workers to grow in their field and create a future of work that’s people-first.

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

There are two quotes that have driven my career choices. The first is “find something you care about and care deeply.” In order to be successful, you need to find your passion, which I’ve found in helping to develop the Skill Economy, and stay fiercely loyal to it. The second quote I live by is to “stay curious.” What makes the future of work so exciting is that there’s always room for innovation and change — so it’s important to stay curious in order to keep progressing.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I’d love to chat with Alexis Ohanian over a meal. Not only is he a groundbreaking entrepreneur and venture capitalist, but he’s a powerful advocate for parental leave and makes time for work and family. As a mother and executive, I understand that finding the right work/life balance is so important. Plus, it wouldn’t hurt if Serena Williams joined us.

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