The Secret Lives of Working Parents

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.”


Pitch Perfect: 3 Questions Every Good Pitch Has to Cover!


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:

  • Why are you uniquely qualified for the role based on your past experience?
  • What are you going to bring to the client that makes you the perfect person for the role?
  • How do you think about the role/ project and what makes you excited to take it on?

Have questions about your pitches and want guidance? You can always reach out to our customer success team at

Featured Member: Leslie Grandy

Time and again, we’ve watched our members parlay a vast and varied array of skills into entirely new careers. Their continued ability to reinvent themselves and seize new opportunities for professional—and personal—growth is nothing short of astonishing, even to us—and this is what we do! Leslie Grandy exemplifies this kind of magic, which is why we chose her for this month’s featured member. Her interview is compelling to us not only because of her accomplishments, which are impressive, indeed, but also for its wise and clear articulation of how to follow in her footsteps, and walking right out of one brilliant career trajectory into another.
Tell us your work story : Who are you and what do you do?
I am a seasoned digital transformation leader with over 15 years experience, and I am especially adept in building high performing global teams that convert physical businesses into savvy digital enterprises. I have over 18 years of executive experience in large public companies like Apple, T-Mobile, Discovery Networks and most recently at Best Buy, where as part of the Renew Blue transformation, I co-founded and grew the company’s first remote technology office to over 125 people and scaled my overall team to 265 people on two continents. While I enjoy working within established enterprises to launch new products or lines of business, I am equally passionate about the opportunity to develop and scale small businesses.
What is the hardest challenge you’ve faced, work-wise?
The hardest challenge I’ve faced was opening up a technology office for a 35 year old Minnesota-based brick-and-mortar retailer in Seattle, the birthplace of Amazon. Attracting qualified talent, building a Seattle-friendly, diverse culture as part of an old school Fortune 100 midwestern business two time zones away challenged all of my leadership skills. I had to understand what rules I could break to make the office competitive and successful, while also having to stay within the corporate lines for operational support. As a woman leader of engineers, designers and product managers, I had to show both empathy and backbone to stand up for what we needed to do our jobs in the world where we were out of sight, and I couldn’t let us fall off the radar. Sometimes it felt as if I had to change everything from the way our internal network needed to enable my remote team to accomplish their work, to how we were perceived as a stodgy old retailer in this high tech community we were sourcing from. And I had to do that while enabling us to achieve – and actually exceed – an aggressive revenue forecast each year.
If you could change one thing about how your given field operates, particularly with regards to women, what would it be and why?
Diversity in hiring takes effort. I believe there are many times where my colleagues do not operate with a growth mindset, but rather tend to operate with confirmation bias about their potential women colleagues. The tendency to do this results in their hiring more of the same, and looking for reasons not to take a flyer on a woman who can do the job but perhaps in a different way, even if it could be just as useful or better than their male counterpart’s performance. The fear and the discomfort of working in a new way can prevent people for being open to what different style or perspective a woman may bring to the situation.
What advice do you have for other women looking to make a career change but who are afraid or lack confidence? How is it on the other side?
I worked for 13 years in the TV/Film industry before switching into technology product management, after pursuing my MBA. I started over from the bottom in tech as an intern, and I was ready to be scrappy, with a strong work ethic and and openness to learn. What I knew about my strengths I leaned heavily into during the internship – showing my problem solving skills, trustworthiness, integrity and commitment. Those became the pillars I built my new career on. What I didn’t know about my job, I set about learning and showed my willingness to take coaching and feedback to fit into the corporate environment that was completely antithetical to my on-set film industry experience. My advice is this: know what your strongest soft skills are, and how they are applicable to your new career. Find out what you don’t yet know about your new career, and make a visible effort to develop yourself in those ways, whether it’s taking a coding class or going to meet-ups. Be willing to start over without ego, and show your potential to learn and grow. (I did a talk at CodeFellows recently on this topic called “Using your Career Strengths to Start Over”. )
Do you have any advice on how to craft a winning pitch?
To make a pitch resonate with a potential client, I always use specific, measurable examples of what I have done previously to illustrate my understanding of and experience in the domain. I believe data always helps someone make a better decision. I also feel it’s important to tailor a pitch to the business and brand in order to show you’ve done your homework and are clear on why you can add value to their team.
What is the best piece of professional advice you’ve ever received? 
Bring solutions, not problems. You own the problem when you identify a solution, and you are more likely to fix it when focused in this way, than you are if you choose to waste time placing blame.
How do you negotiate the balance between life and work when you’re the one setting the boundaries?
It’s always helpful to love your work to make this balance viable. My family knows that when I am happy at work, I am happy at home, and vice versa. So they are a huge part of supporting me in both places. I manage the boundaries fluidly, looking at circumstances discretely to assess the need for unusual working hours, travel and presence. I weigh those requirements against my capacity to succeed with what else my life might demand from me and my family. At different points in time, my reaction to those requirements has been varied. And, I suspect it will continue to be as well.
If you could tell your younger self one thing about what this professional journey would be like, what would you tell her? 
Don’t over plan. Technology – and life – bring new opportunities in unexpected places and it’s important to be open to the possibility that something awaits you that you couldn’t have imagined previously.
How do you make work work for you?
Work works for me best when it is challenging me not merely to use my expertise but to also learn and grow. I think without the chance to learn and grow in my work, it becomes merely a job, and could then be just as well be any job. My life’s work has to include improving and growing myself, and in that process I am better equipped to improve the lives of others, whether they be team members or customers.
Want to be a Featured Member? Fill out this questionnaire and you will be submitted for consideration!

Sallie Says: Just Buy the Latte!

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 Founders Q and A

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.

Mother’s Day Sweepstakes

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.



Flexibility Study Results Are In and It’s Good News For Women!

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:

  • increased gender diversity
  • increased talent retention
  • increased innovation
  • increased productivity

“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?

  • HR needs to partner with other depts to ensure the right work environment and collaboration/ productivity tools are in place.
  • Set defined policies, make sure employees know their options and set clear parameters.
  • Train leaders to manage a remote workforce.
  • Be adaptable to the needs of employees and re-evaluate your policies to ensure they are meeting your employees needs over time.

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!


Pitch Perfect: Head of Product Management


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:


  • She responds directly to the job posting
  • She is clear about her relevant experience and provides examples
  • She shares the secret to her success in similar roles
  • The pitch demonstrates that she understands the big picture and would be a good fit for the opportunity
  • The pitch is clear and to the point
  • She has specific experience with product platform that the job requires.


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

Featured Member: Alexis Jenkins

Often, the savviest career strategies we give our members come directly from other members. Alexis Jenkins is a perfect case in point. The generosity of her insights into how to navigate everything from securing a pitch to negotiating the tricky balance of work and friendship speak volumes.  A self-described problem-solver who truly enjoys helping people and companies, Alexis is a member we’re very proud to feature since she shines a bright light on the importance of personal and professional integrity being the core of every endeavor—which we couldn’t value more here at The Second Shift.
Tell us your work story : Who are you and what do you do?
I’m Alexis Jenkins, and I’m in the business of helping companies scale and define themselves. I’ve worked in Silicon Valley and Silicon Alley. I’ve worked with very small companies and huge companies. I’ve worked  in fashion, SaaS, e-commerce, and non-profit. The thru-line? I genuinely enjoy helping and solving problems.
What is your proudest professional accomplishment?
Creating a company culture and core values for HoneyBook that are still in effect today. I helped set the whole tone of our work environment!
What is the hardest challenge you’ve faced, work-wise?
The hardest challenge I’ve faced was balancing work and friendship with my former co-founder when things got rocky. In the past, our work relationship was fantastic. Once we decided to go into business together—long distance, no less—things started to shift. I made an internal decision before joining this co-venture that if I felt our friendship beginning to suffer at any point, I would walk away from the company in the hope of salvaging the friendship. When that time came, it was shocking and disappointing. My self-esteem and self-worth took a significant beating because I felt like a failure to our company. Now, looking back, I’m happy that our friendship is strong, and that I was able to rebuild my confidence.
If you could change one thing about how your given field operates, particularly with regards to women, what would it be and why?
I hope women continue to be transparent when it comes to their salaries. I’ve learned some of the best lessons about asking for a raise, negotiating a salary and equity, and advocating for equal pay by speaking to my squad, who work in the same field. For me, having financial stability gives me the motivation to put in 200 % every single workday. There’s no better feeling than lying  down at the end of each night and knowing you’ve earned every cent of your paycheck.
What advice do you have for other women looking to make a career change but who are afraid or lack confidence? How is it on the other side?
Start small. Work on something each day that helps you down this new path: create a new email; purchase the URL for your company; write down your goals. Every day needs a task that helps you see yourself in this new career. In the past, I have felt paralyzed and sometimes too proud to ask for help. I’ve learned that my circle of colleagues, friends, and family are there for a time of transition but no one can read your mind. Just talk. Now that I’m on the other side, I feel hopeful and grateful that I didn’t give up on my dream.
Do you have any advice on how to craft a winning pitch?
Have someone read over the project listing and your pitch to make sure you’ve covered everything. Remember to add clear examples of you doing a specific task they require.
What continues to draw you to your chosen field and what do you hope to accomplish in the years ahead?
When I see a mess or hear of a problem, I love cleaning it up and creating a solution. I hope to establish a reputation where I become the go-to person for startups and major brands to resolve big problems they may be facing.
What is the best piece of professional advice you’ve ever received? 
Manifest the life you want! Write it down, meditate, visualize, and work towards creating the professional existence you envision!
Who has been your biggest cheerleader / supporter / mentor?
Shadiah Sigala has been one of my biggest champions. I can call, text, or mail a letter and she will respond, giving me guidance and encouragement. You can follow her on Instagram : @shadiahs
How do you negotiate the balance between life and work when you are the one setting the boundaries?
I don’t apologize any more. As a new mom, at first, I felt like I had to hide that I had just had a baby, that it would make me look undedicated to a role. Now I’ve realized that my family is a part of my professional life because I respect time. Wasting time is no longer an option, so being unapologetic about my needs and asking direct questions to employers allows me to use everyone’s time more wisely. Also, I’ve learned to be more patient and picky about the roles I apply for or the projects I take on. I used to fearlessly enter roles because I just had me to worry about and my lifestyle was different. Now, with a kid, I’ve learned that I can’t say yes to everything if it means taking away copious amounts of time from him.
If you could tell your younger self one thing about what this professional journey would be like, what would you tell her?
What you think you want doesn’t even begin to be your reality—and that’s okay. Buckle up, continue to work extremely hard, and you’ll see it’s for the best.
How do you make work work for you?
By doing things that fit with what I need today and tomorrow. In the past, I used to work based on a 2-year, 5-year, and 10-year-plan. GIRL, BYE! I didn’t know my life would be like this a year ago! So, I work in the present, and I’ve found it’s so much more fun this way
Want to be a Featured Member? Fill out this questionnaire and you will be sumbmitted for consideration!

IFund Women x The Second Shift

We know that there are many Second Shift members who have start-up businesses they are looking to grow or dream of one day starting their own business but don’t know how. If that sounds familiar then mark you calendars:

April 25th at 1pmEST we are hosting a webinar with IFundWomen for Second Shift members interested in entrepreneurship and learning how to grow and fund their own businesses.


iFundWomen is the only crowdfunding ecosystem designed specifically for early-stage, female entrepreneurs, providing a platform for women-led businesses to access capital through rewards-based crowdfunding, expert coaching, professional creative production, a collaborative entrepreneur community, and access to industry connections critical to launching and growing businesses.


Join the iFundWomen Coaching Team on April 25th at 1:00 PM EST for this virtual crowdfunding deep-dive, where you will learn:

1. What exactly rewards-based crowdfunding is
2. If you, and your product or service are right for crowdfunding
3. How to plan a successful campaign through the iFundWomen Method, including pitch honing, network mapping, a rewards strategy & a marketing strategy


Register here and you will receive instruction on how join the zoom chat.…/register/b1177a8e21fbea9966858a512be5123a

So excited for this collaboration and this opportunity for our members!