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!


Pitch Perfect: Presentation

Here is what we love about this pitch:

  • she directly responds to the post itself
  • is clear about her relevant experience
  • argues for what she brings to the client and why she is right for the job
  • she states her rate upfront
  • it is clear and succinct!


Hello! I’m a Creative Director who has made ooodles of Google decks, and I’m super comfortable with the Radical Transparency model. I’m the ideal combo of designer/copywriter to support your project because I will finesse the flow, content, copywriting, and design for IMPACT. I also have a lot of experience with CPG clients. Please check out my portfolio xxxx. I can offer a flat rate if desired, but I’d need to know more about the project scope. Otherwise, hourly is $75. Thank you!


If you have a question about your pitches you can book time to speak directly with our team during office hours:

In person at Luminary the first Thursday of every month  9-10am EST and online the last Monday of the month 12-1pm EST. To book a time email

Featured Member– Lisa Jerles

There are so many different ways to measure success. Women know this better than anyone, and Lisa Jerles downright epitomizes it. A commercial litigator with a truly impressive track record, she left her firm to find meaning on her own terms, prioritizing growth and connectedness, positivity and joy over the thrill—and rancor—of legal combat. We can’t wait to see what she does on this next step of her professional journey—because it’s the journey that matters most. 
Tell us your work story: Who are you and what do you do? 
I was a commercial litigator for ten years with a specialty in business development and strategic planning. I am looking to make a change away from the combative nature of litigation and am currently consulting, using my skills to help businesses improve and grow.
What is your proudest professional accomplishment?
I won a major hearing for a small business to enforce a non-compete agreement between my client and a former employee. Former counsel had lost, but I renewed the motion and won the case. It was a proud moment because the client had very limited resources and I took the case as a favor for a mutual friend. It was very rewarding to provide high-quality legal work for a client who would ordinarily not be able to afford someone who could advocate effectively on their behalf.
What is the hardest challenge you’ve faced, work-wise? 
Leaving my firm. I am very good at what I do and my former partners contact me regularly to gauge my interest in returning. But I got tired of the hostility of litigation. Although I am good at it, it brings negativity into my life that does not comport with my “second shift” as a mom.
If you could change one thing about how your given field operates, particularly with regards to women, what would it be, and why?
The legal profession is riddled with sexism. For example, I was told by a client I got paid too much because I was wearing expensive shoes. But the real problem lies with the younger lawyers—men whose wives stay home and they can’t fathom the juggling that comes with being a six-figure earner and the primary parent. I have been so lucky to be at a firm owned by men whose wives had very successful careers so they pioneered flextime and telecommuting. But, overall, as an industry law has a long way to go.
What advice do you have for other women looking to make a career change but are afraid or lack confidence? How is it on the other side?
I can’t answer this. I don’t feel like I’m on the other side yet.

We All Shine Together!


I recently learned a new term that I love, Shine Theory, coined by Ann Friedman and Aminatou Sow, their basic premise is “I don’t shine if you don’t shine”– meaning women are more powerful if we collaborate and support each other rather than competing and undermining ourselves. What’s interesting to me is how much has changed since they created this theory in 2013.


When Gina and I started The Second Shift in 2014 we could never have predicted the front row seat we would have to witness the social and political changes that would give birth to a new wave of feminism. In the past few years we have seen the rise of #metoo movement exposing the ways women are held back by unfair power dynamics in the workplace. To take matters into our own hands, women are founding businesses at a rate of nearly 2000 a day in the US. Yes, we still account for only 2% of Venture Capital investment, but we’ve gone around the system and created our own venture capital firms and investment avenues to nurture and support female founders.


Consider Wingable_able Partners, a boutique venture capital fund with an emphasis on supporting female founders, partnered with The Wing to create an investment accelerator providing both funding and mentorship. Partner Lisa Blau says, “ A great deal of success—for better or worse—lies in your network. Men have worked this to their advantage for years. We’re bringing that type of network effect to a group that has been overlooked and left out of the network far too long: women. It’s instinctual for women to collaborate so this partnership with The Wing to support talented women was a natural fit.”


Today there is a women’s affinity group, co-working space, networking breakfast for even the most specific interest or community. If you’re entrepreneurial you can join The Riveter, political join The Wing, mid-career leveling up look into Chief, founder join Female Founders Collective, creative sign up with Heymama. As Katya Libin, Heymama co-founder says, “collaboration is the new competition.” This new feminist moment is about finding or creating your own space and seeking comfort with women who make you feel strong and powerful — but not at the expense of anyone else. There is a “more is better” attitude that is a remarkable change from old-fashioned trope about women’s cliques and competitiveness. I should know– I float between them all doing career building and speaking events across the country– and what I have seen is a level of collaboration and cooperation that proves that Shine Theory works.  


For those who say we are operating outside the system and will never crack the glass ceiling of the male-dominated corporate world– I say look at successful female-founded businesses, like iFundWomen, nurtured and funded by female-founded investors to help provide capital and skills for other women founders. Instead of focusing on the glacial pace of change and stagnant statistics… why not focus on the points of light where women are shining and making real progress. It’s a remarkable moment to bear witness to and an exciting time to be in the women’s empowerment business.


Ladies– let’s #shinetogether!


Meet our Featured Member Carolyn Montrose Dub

We are so excited to share our interview with this month’s featured member, Carolyn Montrose Dub. In case you missed her debut television appearance with Jenny on the Today Show you can watch it here!
She is kind enough to offer her hard-earned wisdom and wonderful advice, it exemplifies the kind of generosity and pay-it-forward ethos that can and will inspire real change in the workforce. And we urge you to read her advice on navigating a career change very closely; it’s a veritable GPS.
Tell us your work story: Who are you and what do you do?
My name is Carolyn Montrose Dub and I’m a mom, marketer, volunteer, and runner. After a 14-year corporate marketing career, I became a mom and ventured out on my own, taking on consulting gigs and conducting sales and marketing workshops for teams.
What is your proudest professional accomplishment?
Had you asked me five years ago, I would’ve said winning some award. Today, my proudest professional accomplishment is leading a well-rounded life that includes family, creative marketing projects, volunteer work, and endurance training. I feel balanced, not burned out, and I thoroughly enjoy the work I do.
What is the hardest challenge you’ve faced, work-wise?
The hardest professional challenge I’ve faced is the identity crisis I had after my daughter was born and I left my corporate job. For years, my identity hung on professional accomplishments. When that piece went away, I asked myself daily, Who am I? A mom? A marketer? A leader? I didn’t have the confidence at first to manage both. It took a long time, and a lot of trial and error, to figure out that I could enjoy motherhood and a career.
If you could change one thing about how your given field operates, particularly with regards to women, what would it be, and why?
The perception that a career break means a career is forever broken has to change. We have to work with companies to transform career breaks into breakthroughs for women. How? Better programming and tools that help women prepare for a break, prosper while taking one, and integrate better, if and when they decide to return to full-time work. Training programs, digital tools, grassroots community events for moms and women thinking about starting a family…I could go on all day.
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?
Step 1: Listen. Set up coffee dates with women who’ve chosen different paths. Come prepared with questions, even the hard ones, and listen. Learning breeds confidence.
Step 2: Study your LinkedIn profile and resume. If you are taking a break, think about the things you didn’t have the opportunity to do while working full-time. Examples: networking more, taking a class, pursuing a project that’ll fill a hole in your resume, exploring a new hobby. Choose three of those things and get excited about pursuing them on your own timeline.
Step 3: Brainstorm easy ways to stay on top of your industry. Podcasts, curating news into a social feed, and keeping in touch with former colleagues are easy ways to remain connected and relevant.
Step 4: If you have a partner or spouse, work with them to make sure you can pull it off financially. Understand that you may have to cut back and set those expectations up front. Adding financial stress to the fatigue motherhood guarantees will set you back.
Most importantly, believe that you can do it. When you start doubting yourself, seek support from loved ones.
What continues to draw you to your chosen field and what do you hope to accomplish in the years ahead?
Creativity draws me back to marketing. I’d like to continue to grow my business and show my daughter that creating a life full of color and variety is possible whether you’re a mother or not.
What is the best piece of professional advice you’ve ever received?
People treat you the way you train them to.
Who has been your biggest cheerleader // supporter // mentor? (We love to spread the love here at The Second Shift!)
Early in my career, I worked for a media executive named Laura Schroff. Laura is now a New York Times bestselling author of An Invisible Thread (@lauraaninvisiblethread). She is one of the kindest people I know. She believed in me, opened doors that led to promotions even though she’d be inconvenienced losing an assistant, fought for my tuition reimbursement when I was working full time and in grad school at Columbia, and taught me a lot about media and life. I’m forever grateful for working with her.
How do negotiate the balance between life and work when you are the one setting the boundaries?
It’s about setting expectations more than boundaries. If I go for a run from noon to 1:30PM, I have to be comfortable with opening my laptop from 8-9:30PM to make a deadline the next day.
If you could tell your younger self one thing about what this professional journey would be like, what would you tell her?
Fear does not prevent death, it prevents life (no idea who said this but I love it). Looking back, there are many things I wish I pursued but didn’t because I was scared. Once I realized that I survived every failure I had along the way, I understood that failing is learning and a necessary part of the journey.
How do you make work work for you?
This goes back to setting expectations and creating tenets to live and work by. Mine are: nothing will ever be perfect (mom or not), flexibility doesn’t equal coasting, and every personal and professional opportunity is a gift.
If you are interested in being a Featured Member please fill out this survey

Pitch Perfect: Airline Industry Market Research Project


A Second Shift member is a bigwig in the marketing dept of a major national airline and she was looking for help with a research project. She knew exactly where to come for the expertise she needed– to The Second Shift!  Love when the eco-system works!


Here is the pitch that won the job.


I am a strategic marketing and management consultant with 20+ years of experience working with mid-size and Fortune 500 companies. I also have experience in the publishing industry, having partnered with Meredith Custom Publishing on a custom corporate magazine targeting medical professionals and consumers. My goal is to uncover unique insights and areas of opportunity, while capturing and documenting the industry offerings from a wide variety of perspectives, i.e. content, frequency, visuals, audience, distribution, channels, topics, etc. Each of my analyses includes both executive and detailed findings, as well as specific recommendations that are actionable and relevant.  Thank you for the opportunity and I hope we will talk soon!


If you have a question about your pitches you can book time to speak directly with our team during office hours:

In person at Luminary the first Thursday of every month  9-10am EST and online the last Monday of the month 12-1pm EST. To book a time email