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.

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 members@thesecondshift.com.

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.
https://zoom.us/m…/register/b1177a8e21fbea9966858a512be5123a

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

 

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

Happy Valentine’s Day from Us to You!

Like this pic of our founding team? You too can have a gorgeous headshot taken by the talented and hilarious Sharon Suh. As a Valentine’s Day promotion Sharon is offering 20% off team photos/ headshots with the code SECONDSHIFT.

If you are in the NYC area (she also travels) we hope you take the opportunity to have professional photos taken– it really sets you up for success because you never know when you will need one. Believe us, nobody actually looks that rested and shiny on a good day around here…. There is a major difference between your iphone camera and having someone take your picture and then re-touch it.

So treat yourself and get in touch with Sharon: Sharonsuh333@me.com! 

My Maternity Leave: A Cautionary Tale

I wish The Second Shift existed when I was going out on maternity leave.  As an admittedly type A personality, I plan everything, including the step back in my career that I took a year in advance of getting pregnant.  In my role as a sales manager, I was responsible for a national team and was on the road almost every week.  I was thrilled with my achievements and moved quickly up the corporate ladder. But I knew I wanted to start a family and this was not a schedule that would work once I had a baby.

 

So I left management, took a step back and moved to a new company as an individual contributor. I followed all of the advice I had given my direct reports over the years: I was super buttoned up with my notes, follow-ups and pipeline.  Once I got pregnant and maternity leave was imminent I became me even more diligent. Pregnancy brain be damned–my turnover documents were super thorough. As my belly was expanding I prepped all of my clients about my coverage plans. I had ALWAYS hit my goals, and I was not about to let having a baby tarnish my record.

 

The team covering my leave was an incredible but overworked account manager and a sales manager who was already tapped out with too many internal meetings. So even with all the prep work, I came back to crickets…  No meetings scheduled, a non-existent pipeline and revenue numbers below 50% for Q1. Not having a maternity leave fill-in wasn’t just a bad business decision for me, but for my company as it meant lost revenue for multiple quarters. It wasn’t the fault of my back-up team, they were already stressed about their own jobs and responsibilities. They should never have been made to cover my work– I should have had a backfill. It was a devastating and unnecessarily stressful “welcome back” for a sleep deprived and emotional new mother.

 

….If there had been a The Second Shift I likely would not have chosen to take a step back in my career path and leave my sales management role. I would have realized there were other options for my growth.

….If there had been The Second Shift I would have found the perfect member to fill in during my leave. We could have worked together to prepare ahead of my birth and she could have been there to assist me during my transition back. I would have felt supported and my team would have not resented me for the extra work they shouldered while I was gone. Work could have continued on successfully and my sales numbers would have reflected the positive effects of an unbroken workflow with no loss of momentum.

 

The Second Shift offers you options and takes the burden off parents, families, and co-workers. And I am proud to be a part of this team that supports and encourages female growth and keeps women engaged in the workforce.

Mind the Gap

There is a really interesting article in Fortune about why the pay gap persists in lucrative fields where with plentiful female talent. For example:

 

“The difference is even more pronounced for financial managers, where there’s a 35% gap. And in the legal field, the average salary for men is $140,270—a full 24% more than the $106,837 women earn.“

 

Why? We know why:

 

-sexism and discrimination

-women having children during the most demanding years to get ahead

-women taking lower paying less high-profile jobs to juggle career and family

-women negotiating poorly for themselves

 

What is interesting is seeing what is being done about it, not enough!

 

-many tech firms doing yearly salary audits and leveling up gender pay inequity

-pay equity laws in 40 states

-20 states do not allow employers to ask salary history

 

With 100 women in Congress in 2019 it will be exciting to see if more female/ family friendly legislation is passed. in the meantime, we encourage employers to learn about how The Second Shift can help you retain and attract critical, mid-career professional women to #superchargeyourwork.

 

Reach out to info@thesecondshift.com