I’m very thoughtful about what I take on and the people who work with and for me. I make sure that I keep my non-negoitables foremost in my mind when choosing what to say yes to.

I’m very thoughtful about what I take on and the people who work with and for me. I make sure that I keep my non-negoitables foremost in my mind when choosing what to say yes to.
A note from Jenny:
The idea of normalizing the conversation about parenting in the workplace is very important. A recent personal story written in The Atlantic highlights the importance of candor about the realities of family in the workplace and the lengths people go, ineffectually, to hide one side from the other:
“Why would people do this? Why pretend kids are of “little importance”? When work and parenting seem at odds—because our culture tells us they’re at odds—mothers and fathers feel forced to demonstrate their commitment to one (the work side) by minimizing their concern for the other (the parenting side). They do not want their bosses to think they are anything other than 100 percent committed. “
Employees cannot feel afraid of what might make someone else uncomfortable– aren’t they told by leadership to “bring your whole-self to work?” I am the boss and just this morning I was fearful about revealing a personal detail at work– I realized too late that I booked a meeting with a (female) investor too close to my son’s birthday party. I thought about pretending it was a different conflict but then decided to bring my “whole-self” to the conversation. I owned up to the mistake and the reason why I had to reschedule–it felt scary but freeing to choose to make be bold and vulnerable. Ultimately, if the investor didn’t get it then I don’t want to do business with them.
At The Second Shift, we try to create a world where we don’t compartmentalize life and work. I don’t want my employees to waste time and energy trying to figure out how to make it to ballet or to a doctor appointment with an ill parent. Better they just do their job efficiently and are responsible– I do this myself and need to trust them to be grown ups and do the same.
“Put simply, mothers and fathers ought to come clean about the nature of their lives. We can’t fix problems that we pretend don’t exist; we can’t improve the lot of parents at work if we pretend we aren’t parents.”
Strong team leader, savvy marketer, and collaborative worker. I’ve run marketing teams big & small, in-house and as an external source. I understand how to get the most from teams and execute successful and clever plans. For example, as Head of Marketing for XXX, I successfully re-launched the brand with a 360 degree campaign which included a pop-up shop, PR campaign, music/celebrity partnership, event, digital campaign and more. At XXX I oversaw new club opening and market entries, as part of the marketing team – successfully doubling the business with guerrilla tactics. Today I run my own marketing consulting business where I craft and execute my client’s marketing strategies. One of my clients is a fertility start-up. I am assisting them with brand definition, pivot, marketing strategies and events – all very relevant to the role at XXX. I am based in Carroll Gardens, Brooklyn with my 18 month old. I get it! I am living your target market! Let’s connect.
This winning pitch covers the three questions every good pitch should address:
Have questions about your pitches and want guidance? You can always reach out to our customer success team at members@thesecondshift.com
Sallie Krawcheck busting myths about women and money in an article on the ways women are spoken down to when it comes to money and equity. Her message– buy the latte! Don’t let society tell you to save the latte cash and you will be rich or you have to choose if you are a Carrie (buys shoes) or a Miranda (saves money). This is a distraction from focusing on the systemic issues that keep women from gender equity.
“….as infuriating as it is to be patronized, that’s not the biggest issue. All this nonsense about lattes and shoes is shifting the attention–and thus the blame–for the underlying systemic money challenges women face, to the women themselves. The pink tax, the wage gap, the debt gap, the funding gap, the domestic work (and emotional labor) gap, and–my personal crusade–the investing gap.”
Sallie and her company Ellevest are taking power back into the hands of women with skills building, investment advice and financial tools to level the playing field. Because, she says, “As Gloria Steinem has said,– We will not solve the feminization of power until we solve the masculinity of wealth. So, ladies, buy the f***ing latte, because I’m going to need you caffeinated when we do this thing.”
Oliver Guide is a crowdsourced travel platform where user share their travel recommendations for the community. It’s founders, Cynthia Pillsbury and Courtney Leary, are two mothers who love to travel with their families and created a platform to aggregate the information and tips they got from friends. In the spirit of celebrating family and travel and our community they are hosting a sweepstakes for our members to win some of their fave travel accessories.
What is Oliver Guide?
A platform for capturing and sharing travel recommendations.
You are both busy mothers with jobs– what inspired you to create this platform?
A need. We were both traveling a lot and asking friends for recommendations on where to stay, eat and what to do as friends and friends of friends are the people we trust the most when it comes to travel. At the same time were being asked to share our travel information which meant that we were going back to old emails and doing a lot of time consuming cutting and pasting. Oliver Guide solves that– once you create a guide, you can share it with others forever. And, you can access travel recommendations from friends with ease.
Cynthia– as a Second Shift member, do you have advice for any other women thinking about standing up a new business venture but feeling overwhelmed?
Remember to have fun with it. If you don’t love it and believe in it, don’t do it. Also, take it one step at a time, remember Rome wasn’t built in a day and often times the best ideas evolve with time, trail and error (yes error!).
What are your favorite travel destinations?
Courtney: Always love France, Santa Barbara and New York, but someplace new is the best.
Cynthia: I have my stand-bys – Vail and Nantucket, but have made a promise to take my children somewhere NEW and different every year. We loved Belize and Laos. Next on the list is (hopefully) Greece for kids and Japan for adults.
Best advice/tip you’ve learned through an Oliver Guide?
Courtney: How to do Art Basel, Miami. It was something overwhelming that turned into absolute fun once I knew what to do!
Cynthia: Traveling with children is not for the faint at heart. I love to go go go, but that does not always work for so we do… a little culture, a little beach (chill time), a little culture, and so on. I also download Google maps before I get to a location and have my Oliver Guide accessible via a screen grab (if I am not able to have cellular) so I have a plan of attack on the days’ activities. |
In honor of Mother’s Day we are holding a sweepstakes with Oliver Guide!
If you sign up for their amazing travel site between May 1 and 10th you are automatically entered to win some awesome gifts:
For those who don’t know, Oliver Guide is a platform for capturing and sharing travel recommendations. The founders are mothers who love to travel with their families and wanted to crowdsource info from like-minded adventurers. One of the founders, Cynthia Pillsbury, is a veteran Second Shift member and she shares her story and travel insights here! As a Second Shift member she knows intimately how hard the juggle is and wanted to honor our community with some fun travel related gifts.
Stay tuned soon to see Jenny’s Oliver Guide post on her own families trip to the Middle East.
A new global talent trends study was released by LinkedIn and the among the biggest trends in the workforce is the move toward more flexibility. This is great news for The Second Shift and women! When we launched in 2015 flexibility was seen as something too disruptive and too progressive for many organizations to consider. Today things are rapidly changing as the need to attract and retain talent is a strategic initiative for hiring managers and studies the myriad benefits of a flexible work environment including:
“According to research by Werk, a people analytics software startup that helps companies improve their flexibility performance, the most in-demand types of flexibility are the ability to work remotely at times while keeping an assigned desk, the autonomy to step away for a few hours for personal reasons, and the freedom to shift hours (e.g., to avoid rush-hour traffic). “
So what’s a business to do if they want to become more flexible and are afraid of disrupting the status quo?
The Second Shift has thousands of women looking for just these types of work arrangements and we are happy to fill your open roles and provide a roadmap to hire and back-up your flexible employees!
A client is looking for a Head of Product Management who can spin off a new product category and lead eight teams from strategy until launch. Here is a pitch that we thought really hit the mark!
Having built and managed product teams in both small and matrixed organizations, I am keenly aware of what it takes to lead high-performing teams. I would love the opportunity to help XXX scale the XXX platform and marketplace teams to enhance and enrich a very powerful suite of design tools. On XXX Digital Products team, our UX and Interaction designers leveraged components of the IXXX, enabling our platform teams (mobile, web, connected TV, etc) to quickly launch and iterate based on market and customer feedback. My team was then able to pivot from platform work, to focus on enhancing the customer experience and leveraged our user and behavioural data to help inform the next generation of our XXX product. As a product leader, I have found success because I understand the importance of collaboration across functional teams as well as transparency when discussing critical issues and business priorities. My product experience makes me a strong fit for the project and I look forward to discussing the role with you in more detail. Thank you!
Why we like it:
If you have a question about your pitches you can book time to speak directly with our team during office hours:
The last Monday of the month 12-1pm EST. To book a time email members@thesecondshift.com.