3 takeaways from our conversation with SNL Producer Lindsay Shookus

Jenna Vassallo

Jan 15, 2025

Lindsay Shookus is an Emmy-winning producer well known for her 20-year career at Saturday Night Live.

Starting as a 22-year-old assistant and rising to senior producer, Lindsay played a pivotal role in booking celebrity hosts, scouting new comedic talent and shaping the show’s cultural legacy.

During her time at SNL, Lindsay became a mother—just as she stepped into a leadership role—and continued to climb the ranks. Balancing the demands of a high-stake role and new motherhood, she proved that ambition and adaptability could coexist.

After two decades with the network, Lindsay transitioned from live TV to build a diverse portfolio that includes public speaking, producing documentaries, and founding Women Work F*cking Hard, a community dedicated to uplifting and supporting women.

We spoke to Lindsay to kick off season two of The False Tradeoff, where she shares how she juggled motherhood and a high-pressure career—and why she ultimately took the leap into the unknown after two decades at one of TV’s most legendary institutions.

Here are three takeaways from the conversation:

The False Tradeoff episode 33 with Lindsay Shookus

Episode 33

The False Tradeoff

Lindsay Shookus on 20 years with SNL, motherhood & reinventing yourself

Listen to the episode

1. Success happens when you show up and say yes

Lindsay’s career trajectory was built on her relentless drive and willingness to take on any task. Starting as an assistant, she became what she calls a “job collector,” volunteering for the tasks no one else wanted—like showing up at 6 a.m. shoots or managing behind-the-scenes logistics.

“It was a little bit of luck and a lot of drive,” she reflected on her early days. Her willingness to step up earned her trust, visibility and eventually a leadership role. Lindsay’s journey is a reminder that saying yes to even the smallest opportunities can lead to incredible growth.

2. Motherhood cracks you open in the best way

For Lindsay, becoming a mother was a transformative moment—personally and professionally. Stepping into her dream leadership role while preparing for motherhood, “felt like two dreams coming true at once, but it was also terrifying,” she shared.

Motherhood forced her to let go of perfectionism and embrace vulnerability. “I started letting people in more, admitting when I wasn’t having the best day,” she explained. This openness deepened her relationships and made her a more relatable leader—a powerful reminder of the strength in showing our human side.

3. Identity beyond a dream job

After 20 years at SNL, leaving the show felt like stepping off a cliff for Lindsay. She grew up on the show and it was part of her identity. But taking that leap opened the door to a fulfilling, multifaceted career.

Now Lindsay embraces the uncertainty of what comes next: “When you go where there’s light and heat, the world opens up in ways you never imagined.” Her story reminds us that our identity isn’t tied to a title or company—it’s rooted in the values and passions we carry forward.

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To celebrate all we’ve accomplished, our team shared what they’re most proud of since joining the team:

I'm most proud of how much we have done to improve the single hardest moment for women's careers (going on parental leave) ... one that is often shrouded in insecurity and fear. We've been able to help advocate for so many women (and men!) in a way that is empowering and truly life-changing.

Allison Whalen, CEO & Founder

What am I most proud of? Growth! Growing a category of support that didn't exist before Parentaly. Growing from a one-woman bootstrapped operation to a global team of 25+ employees and coaches. Growing our overall impact for working parents, with companies investing in our parental leave programming to support employees all over the world. And growing as humans: new babies, new friends, new life experiences... all while tackling new and exciting work challenges together.

Rich Burke, Head of Growth

When I reflect on what I am personally most proud of during my time here, it's working alongside a team where we constantly evolve and optimize everything that we do in order to deliver the best possible experience for the folks going through our programs. It sounds cheesy, but there are processes that my team and I used to do 100% manually that are now completely automated and systems in place that have become second nature to how we operate. Working with such thoughtful, smart, and creative people is incredible.

Sara Ophoff, Senior Program Manager

I’m most proud about doing work that makes parents feel confident and empowered about their careers during a time that can be overwhelming and challenging – not only for our clients and users who go through Parentaly’s programs, but also with our advocacy work on LinkedIn, through our podcast and other big campaigns that make a difference. It’s been pretty rewarding to build a brand people know and love because what we’re doing resonates with so many employees’ experiences in the workforce.

Jenna Vassallo, Head of Brand & Marketing

I am so proud of the way we've approached growth with such care and intentionality - with every adjustment we've made to our offerings, we've never lost sight of our goal to provide the most supportive and valuable experience for our users. I love looking back on the early stages of conversations and building that have led us to the experience we offer today. Personally, I am extremely proud of the work I've done to scale and automate our backend!

Rachel Andes, Program Associate

I am most proud of the work we do every single day to make a positive impact on working parents! Everyday I get to work with an amazing group of people…we work hard but we also have fun.

‍Sarah Gruber, Client Partner

I'm proud of scaling an employee experience that consistently delivers positive outcomes for new parents and their organizations. Our north star has always been the user, and we never sacrifice our high quality bar!

Mansi Kothari, VP of Product & Experience

I feel a sense of pride that I get to work behind the scenes supporting everyone. I’m proud to see all of the collaboration between the team and how Parentaly positively impacts employees.

Leo Manalo, Executive Assistant

I'm most proud of going through the Parentaly program myself! I'm so proud to work for and promote this company in a time where parental leave and supportive policies are at the forefront of a national conversation. But beyond this, I'm most proud to call myself a participant.

Emmy Carragher, Enterprise Partnerships

I’m really proud of the work I did to expand our coaching bench globally at Parentaly. It was so rewarding, not to mention insightful, to connect with talented coaches from around the globe. This expansion not only enriched our coaching offerings but also strengthened our commitment to making a meaningful impact on families all over the world.

‍Nicole Hagemann-Bex, Senior Coaching Operations Manager

I have tremendous pride in the knowledge that what I am doing will change the career landscape for new parents, particularly mothers. This will make it more likely that my daughter can have a career AND a family without worrying about the unintentional negative impact of taking parental leave. Nothing makes me prouder than that.

Mindy Himmel-Brown, Strategic Partnerships

In my short time at Parentaly, I'm proudest of the work we're doing with our clients' ERG groups to elevate the stories and advice of actual working parents. It's such an impactful way to spread the word about Parentaly as an essential resource for all people growing their families, and the managers who support them!

Alex Diskin, Enterprise Account Manager

I'm most proud about using LinkedIn to connect with others. I was recently able to share a helpful return to work doc with 50+ new people looking to make a difference at their company. Was pretty cool that people from Chewy, McDonald's, Honda, Cisco, AWS, Walmart and more want to integrate just a piece of what we have to offer. Also...I'm so proud of the way I feel as an employee at Parentaly. For the first time in my career my personal interests align with my professional interests and I've never felt more motivated.

Jenny Hurwitz, Strategic Partnerships

I'm really proud of being able to help the Experience team by handling the supportive functions so they can focus on the bigger picture. It feels great to know that I’m making things easier for them and contributing to the team’s success.

James Mango, Executive Assistant

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