Sherrill Kaplan, VP, Head of Marketing & Sales – Zipcar

You know one of those women you admire for both her smarts & spunk? That’s Sherrill Kaplan. I first met Sherrill while we both bled pink and orange – running digital marketing & innovation for Dunkin’ – and was always impressed by her work ethic, relatability and intrapreneurial nature. Now, as Head of Marketing & Sales for Zipcar, Sherrill brings her passion for all things digital into the sharing economy. As someone who’s wired to be connected, we spoke about how she manages to turn off.

This interview was conducted in Boston & was condensed and edited for clarity.

Catching Up

Something’s missing; we didn’t SoulCycle before this interview! I heard you recently completed your 500th ride.

I know, it’s now our thing. My first class was about 5 years ago (don’t add up the bill) and I cried through the whole thing.

*For anyone who’s confused by crying @ the gym, make sense of it here.

Same here. Is SoulCycle your ‘Sherrill space?’

Yes, it’s one of the only times I can truly think – from the moment my eyes open each morning, I have anywhere from 1-4 other people in bed with me and I feel I’m always running on a hamster wheel. When I need a reset, to think through something at work, or step outside my body, it’s those 45 minutes.

It’s ironic – SoulCycle instructors tell you not to think about work during class but inevitably, you do.

It’s typically that song after arms [laughs], where they’re saying inspirational things, that your mind wanders. Each instructor finds a way to connect to every single person in that room – all they’re doing is realizing we’re all human and in this together. Whether it’s not appreciating yourself enough or needing a push to realize your potential, those are universal truths they’ve latched onto. I swear this is not a SoulCycle commercial!

A Look Back

The energy you bring to SoulCycle you also bring to work. Take us through your professional journey thus far.

Did you know my undergrad degree is in special education? Senior year, one of my advisors told me: “This career is really hard. Try something else first. You can always come back.” So I listened, grateful someone told me what to do.

I had taken a business class and enjoyed it, so that was enough for me! I went off to business school thinking I’d be a school administrator. I tend to “gut” and not over-research.

It’s good to know that about yourself. After business school, Citi  came calling – connect those dots for us.

I was recruited into Citi’s rotational, management associate program, which worked well as I was one of the only MBAs without years of business experience. I started out in NYC in back office credit card operations. We worked with huge pieces of equipment that received checks & sent statements. I was enabling the business on the back-end but became interested in a front-end marketing rotation. After a few years on the Citi marketing team, I moved into card acquisition at Amex and later, membership & loyalty where I managed the Membership Rewards gift card program.

Do you consider Amex where you began your leadership track?

Yes, Amex is where I got my first director role and I suddenly found myself regarded differently in the marketplace. I loved my time at Amex but Adam, my husband, had just landed a job in Boston and we were pregnant. He moved to Boston and I stayed – trying to figure out how I could stay with Amex and work remotely. This was 2008, and the workplace hadn’t made the shift to the remote culture we enjoy today.

Eventually Dunkin’ came calling and good thing they did.

Yes, it was a good run. When I started, I led the gift card and loyalty programs – in 2011, we were sending Dunkin’ cardholders paper coupons in the mail!  By the time I left 7 years later, I was leading digital marketing & innovation, which meant I oversaw mobile, loyalty, CRM, mobile ordering, payments and more. Looking back, technology was part of everything I did, but I never really looked at it that way.

I was recently speaking with someone in the industry who boiled it down to the fact that digital is just a channel for good marketing & storytelling. I’d never looked at it that way, and like that take. Was it an uphill battle to digitize the business?

Incredibly challenging. In the beginning, franchisees weren’t happy with the loyalty program and told me to come back to them when we had something better. It became a turning point. We had the blessing of a blank page. We hired Digitas as an agency partner and together, we built the loyalty program that exists today, DD Perks.

At Work & At Home

Quite a ride at Dunkin’. Now you’re overseeing marketing & sales for Zipcar. Where do you focus your time & how has the business been impacted by the recently IPO-ed Uber & Lyft?

Zipcar is a performance marketing engine, but in this role I’ve expanded my remit to include areas I hadn’t yet managed directly like media and brand.  We’re doing a lot of insights work right now to fully understand consumer mindsets and behaviors, which will translate to a refreshed brand expression.  It’s been fascinating.

The popularity of ride sharing has impacted the short-distance use case for Zipcar, however our members use Zipcar for a variety of reasons.  Our primary competition is not Uber or Lyft, it’s personal car ownership. So, the more mobility options people have (e.g. – ride sharing, bikes, public transport, car sharing etc.), the more likely they are to shed a personally owned car or never buy one in the first place!

Switching gears, you’re in an always-on role in a fast-paced industry. With three young girls at home, how do you set an example for them when it comes to technology?

It’s so, so hard. I had the gift of some time to reflect before starting at Zipcar. First, I realized the aforementioned hamster wheel doesn’t stop, so moving forward, it was on me to create my own boundaries. I also realized there’s so much happening in my kid’s lives during the day – their lives are lived while I’m at work.

Something amazing may happen at school at 9am and by the time I’m home at 6pm, it’s long gone from their memory. I reflected on that and remembered that often…I’d come home, rush to put them to bed, just so I could work some more. How ridiculous is that? I realized I was missing being present in their lives living like this. Part of it was self-inflicted, but I concluded no one at work is going to tell me to spend more time with my children – it was on me.

So in that time off, you vowed to be better about it.

Yes, I was very open with my new team at Zipcar about the importance of my other job – being a present mom to 3 amazing kids. They know if I’m not answering emails, it’s because I’m with my family… and I encourage them to do the same.

You have a nanny – do you receive judgment from other working moms?

I’m sure I do. But here’s another thing I’m working on… I’m trying not to care as much about people’s judgements of me. I am learning I can’t please everybody so I just try to do the best I can. On the personal front, I truly believe my kids are better kids because they’ve had 3 parents. Our nanny, Maria, is part of our family, and my kids benefit from all the things that she is that I am not.  She also recently moved in as Adam took on a new role that requires more travel. It’s a huge help but still, my life is like a game of whack-a-mole, juggling everything and putting fires out one at a time.

You’re harder on yourself than you realize. I still remember a meeting where we were trying to schedule a Friday follow-up; you were willing to make any time work, except a few hours of scheduled 1:1 time with your daughter. That stuck with me because I never heard anyone else state a boundary like that.

That makes me really happy to hear.

Speaking of scheduling 1:1 time, how do you try and teach your kids to have a healthy relationship with technology?

I probably overcompensate. They’re not allowed to watch TV or use the computer during the week. Weekends are different but I’m okay with that because there’s benefit in downtime. I could be creating a monster here in that they feel deprived, but it works for us right now. It’s funny though, they’re starting to notice how much we’re on our phones and mention it to us. So I now leave my phone behind when I help them get ready for bed so there’s not that distraction.

What I’m sensing is your identity was tied to work for a long time & now, you’re consciously trying to change that.

That’s 100% right. I didn’t realize I had fallen into that trap until I had some space, and it’s been a blessing. I’m now a better leader, wife, mother, daughter and friend because of it.

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Previous interviews:

• Just go (travel that is) – how to drop everything & backpack Latin America
• Spotlight on Amazon’s leadership principles
• Relatability, empathy, kindness: debunking “the myth of the nice girl”

Brian Moseley, Partner Sales Manager, Amazon Web Services

What’s it like to work for one of the world’s most innovative companies? Behind any high growth company is a unique culture – we sat down with Brian Moseley, a tenured sales professional in Boston’s tech scene, for his take on the famed Amazon “Leadership Principles” (also pasted below, courtesy of Amazon’s website).

In our first podcast-style interview, we cover personal favorites (“have backbone, disagree and commit”), how some of the principles contradict themselves in an effort to create productive tension and how these principles drive culture – from the narrative process and PR/FAQ to the 2 pizza rule.

Listen here. [30 min]

Bianca Olson, SVP Corporate Affairs, Houghton Mifflin Harcourt

Bianca is one of the original girl bosses in my professional life. We worked together in the PR agency world and I always admired her friendly yet authoritative demeanor and serious style from afar (not true, we sat 20 feet from each other). Being in close physical proximity meant I, bright-eyed and fresh out of undergrad, picked up on most interactions and as a result, invaluable teaching moments.

Today, Bianca is Senior Vice President, Corporate Affairs at Houghton Mifflin Harcourt, a learning company that serves 50 million students and 3 million teachers in 150 countries, and is home to  brands like Carmen San Diego* and Curious George. We caught up in downtown Boston; this interview was condensed and edited for clarity.

*As a kid, I was OBSESSED with the Carmen San Diego computer game – when Bianca mentioned it, a light bulb went off. Seems I have the trench coat-clad character to thank for seeding my passion for travel at an early age.

Catching Up

Bianca, we worked together a decade ago and while you look exactly the same, I know a lot has changed. As a new mom, how are you adapting at work?

Becoming a mom when you’re more senior in your career has its pros and cons. By this stage, you’re pretty set in your ways, and have a certain schedule and way of getting things done. It took time for my husband and I to have our son – who is almost two years old now – and like any new parent, I want to spend as much time with him as possible. Seeing him before he goes to bed means leaving the office at 5pm. I used to have that time after hours to get things done; now, I’ve adjusted by coming in early and using that as my quiet, productive time. I would say I’m able to do more in less time now, though my husband would disagree with the “less time” part!

You were always efficient. Are you more disciplined now about only working on high value needs?

I try to be strategic about where I spend my time but the small things matter. I’ve talked to some people who say now that they have kids, they’re all business at the office – no small talk so they can do their job and leave. That’s just not me – it sounds terrible! While a good percentage of the organization is remote, most of my team is here in Boston, which I love. I oversee corporate affairs, which includes internal comms, external comms, corporate social responsibility, national events and sponsorships and our history initiatives so I view all of our work as incredibly high value. I love my team and what we do, and I believe that personal relationships are part of what make us effective in our jobs. Plus, we spend too much time at work not to have fun while we’re there.

Early Influences & Leadership Style

We’re very similar, both detail-oriented. How have you learned to relinquish control as you’ve risen through the ranks?

In communications, everything we do is visible, both internally and externally. With 4,000 employees, when something isn’t perfect, we hear about it – especially in a company and culture that values the written word. Part of being able to give up control is trusting the people you work with – that means hiring people who value the same things, like great writing and a similar obsession with details. All you can do is make sure you have the right team in place and create a culture of high standards. I’ve always believed that when you hand something off internally, it should be “client-ready” – that sentiment has carried over from my agency days.

I recently read: “Great bosses change us for the better. They see more in us than we see in ourselves, and they help us learn to see it too” (read more here). Who was one of your earliest professional influences?

I absolutely think that’s critical – a good leader trusts their team and helps them take on more than they thought they could. I’ve definitely benefited from that when I think about the great, early bosses I’ve had. My first boss in the agency world really instilled a sense of accountability from day one. He coached me to understand that even as the most junior person on the team, I was responsible for very important things. I still find myself doing things today that I picked up from those days – things as small as writing “AI” in my notebook when something is an “action item” to ensure it stands out. He taught me regardless of your position within the team or organization, you have to be highly accountable.

Such accountability probably helped shape your early professional successes. As a young manager, how did you try to develop your leadership style while still learning to lead yourself? What about situations where you’ve become a boss to a peer or someone who may have more experience than you?

I think relatability, empathy and kindness – all of those things – are important leadership skills. When becoming a manager of a peer or someone with more tenure, it helps to view yourself as a coach vs. a “manager.” A coach wants to make people feel supported in their work and empower them to do their best. When people view you as a supporter and a partner, age or experience is less of an issue.

Was there ever a point where you sat down and pointedly asked yourself: “what is my leadership style?”

Actually, yes. About 6 years ago, my manager at the time said to me: “you’re at the stage in your career where you need to think about what type of leader you want to be.” Until that point, I had focused on working hard, doing my best, being a good person and treating others with kindness and respect, and found if I did those things, I could be successful. But as you progress, sometimes those things aren’t enough and you need to be more intentional. I took a step back and looked at others who I thought were great leaders and who I wanted to emulate. And just as helpful, I thought about what I didn’t want to emulate. Sometimes you encounter people with a style you know is not the way you want to lead. In those cases, I tell myself “take a mental note right now & make sure you’re not doing that.” Those are valuable moments.

Intention is key so you can actively vs. passively become a certain type of leader. I recently attended a leadership seminar with the philosophy that there’s no set of inherent traits that inherently make a leader; if there were, people would see they’re missing certain characteristics and automatically screen themselves out as a good leader. So, the concept was that leadership is not determined by a set of qualities, but rather being an authentic listener. How would you respond to this?

I think that authentic listening is a leadership quality in itself, and there are certain traits that accompany it. Authentic listeners are present, they care and are genuinely interested. Those are all important qualities. But listening can’t stand alone; there has to be another side – things like decisiveness and the ability to put forth a vision, for instance.

Leaders must lead. I’ll never forget a time I was struggling at the office. A manager pulled me aside and stated he could tell something was going on that was impacting my work. He knew the quality of my work was of the utmost importance to me and no questions asked, told me to take a few days off to reset. He was kind, caring & direct.

That’s amazing. Great leaders care about their teams as people. We use Gallup for employee engagement benchmarking and they have a very prescriptive, twelve question methodology. Q10 asks: “do you have a best friend at work?”. It’s the first year the question’s been asked and everyone is talking about it. It made its way onto the list because after years of conducting the poll, Gallup saw that it was a critical factor in workplace engagement. It’s not necessarily about having a ‘best friend,’ but instead what lies beneath that – a certain level of closeness with people you work with. According to Gallup, at the end of the day, the best predictor of employee engagement is the people you work with.

Evolution

There’s clearly a thread of kindness and inclusiveness throughout our discussion. You must’ve learned these traits at a young age and then carried them into the workplace. On a personal level, who’s impacted you the most?

My mom is the most empathetic person I know, so I grew up learning to look at things from others’ perspectives. That’s been critical at work. Today, my husband continues to teach me things, like how important it is to stop talking sometimes, to say less. Have you seen those little cards at Paper Source? They’re intended as jokes to give out at cocktail parties, and some say “stop talking.” I bought them for Matt to give to me. He communicates very well with fewer words.

Ha! The older I get, I’m more and more impressed by people who are concise and crystal clear.

Yes! He’ll often say “I’m already sold, you don’t need to keep proving your point!” I think that’s a valuable lesson to carry over into my professional life and I try to remember it. You need to know when to stop selling.

This goes back to authentic listening. Many of us listen to react, be it to agree or disagree or to comment. Earlier you mentioned your approach to managing people at different levels. Conventional wisdom tells us as a leader, you can’t have all “A” players. How do you maximize “B” and “C” players’ contributions?

Interesting. Another question on the Gallup survey, Q3, asks whether people have the opportunity to do their best work every day. It’s about making sure the right people are in the right roles – identifying what people are motivated by and best at to help gauge where they’ll be most effective and most engaged. At the end of the day, people want their work to have an impact. HMH is in a double bottom line business so our work has a positive impact on society – that drives passion and meaning for a lot of people, but as a leader you also need to help make sure people are in roles where they can apply their talents. On the flip side, sometimes you need to acknowledge when the right role for someone may not be on your team or even within the company, and while it can be hard, you have to be honest about that.

It’s about getting someone to do their best work. Okay last question, and shifting gears a bit. You’ve always been very authentically you. How do you ensure your personal style doesn’t overshadow substance?

Individuality has worked for me. Of course knowing your audience is key – you need to be able to read the room – but if your personality plays to what you’re doing, it’s often welcome. I’m recalling a local event where some folks had a negative reaction to a speaker who was a senior-level female executive in the Boston business community because she didn’t come across as overly serious. I had the opposite reaction because I appreciated how genuine she was. She wasn’t trying to be too corporate or overly polished and she got to where she was because of that, or possibly despite that. To me, that’s refreshing and deserves respect.

Personality is what differentiates us.

Yes, and starting out in a predominantly female environment on the agency side, I don’t think I ever felt like I had to suppress my personality. It was never a male / female thing, but more about being in a supportive environment that values creativity. This reminds me of a book HMH published last year called “The Myth of the Nice Girl,” by Fran Hauser. Her premise is that women don’t have to sacrifice their values or hide their authentic selves to be successful. I’ve always challenged the notion that warmth and kindness are characteristics women should avoid; in fact, I think they’re what makes us such effective leaders. It’s like the Maya Angelou quote: “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”  For me, that’s what great leadership is about.

More on kindness & leadership?

• How Purposeful Kindness Can Make You A Better Leader

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