Jessica Winder built a career out of learning exactly how corporate America works, then decided to teach other people how to work it too.

She is Chief People Officer at her Winder Law Firm, a career coach, and mom of four, including two sets of twins born seventeen months apart. After building an entire household team to make her career and her family both possible—from a live-in house manager to a set of core work hours she and her husband both protect—she started talking openly on LinkedIn about what she saw behind the curtain of HR. That honesty turned into a podcast, a speaking career, and a client list full of women trying to get promoted, come back from maternity leave, or figure out if they want to come back at all.

Jessica shares why she believes the 40 hour work week was never built for people with families, and why she thinks having it all really just means paying other people to help you get it. She also explains what she tells women before they go on maternity leave, how she decides which coaching clients are actually the right fit for her, and why she tells everyone to get the title before they ever think about getting the raise.

Jump into the conversation:

(00:00) Meet Jessica Winder

(04:45) On having two sets of twins in seventeen months

(07:26) The team behind the scenes at home

(12:12) How much she and her husband actually work

(16:47) Her two maternity leaves and what she would tell other moms

(23:40) From ranting on LinkedIn to building a media business

(26:23) Why the 40 hour workweek was never built for parents

(28:39) Inside her podcast, Make It Make Sense

(32:40) Coaching moms through the decision to go back to work

(35:44) How to know if your career coach actually knows what they are doing

(41:00) Why you should get the title before you get the raise

(43:57) Save of the week

Connect with Mallory Lee: https://www.linkedin.com/in/mallorylee/

Connect with Shannon Curran: https://www.linkedin.com/in/shannon-sweeny-curran/

Connect with Jessica Winder: https://www.linkedin.com/in/jessicadwinder/

Check out Winder Law Firm: https://www.linkedin.com/company/winder-law-firm/

Produced in partnership with Share Your Genius

www.shareyourgenius.com

Heather Bell spent years in tech sales as the only woman in leadership, and now works in MarTech at Vector after building her career at OpenTable. After years of watching gender shape who got access to relationships and opportunities on sales teams, she began rethinking what she actually needed from a job to stay in the industry long term. Her search for the right fit included being the only woman in leadership at a security tech company, hiding that she was a mom during interviews, and leaving a role once she realized her sponsor could not take her to the after hours meetings where relationships and opportunities actually got built.

Heather shares why she finally stopped trying to be the torch bearer for every woman in the room, and what she looks for now so she's never the only woman or the only working parent in leadership again. She also explains why remote work became less about convenience and more about equity, how she uses the same skills from sales leadership to advocate for her son at school, and why something as small as a company's swag closet can reveal whether its values are real.

Jump into the conversation:

(00:00) Meet Heather Bell
(01:27) Working in tech sales at Vector and OpenTable
(05:13) On being the only woman in leadership
(07:01) The day she left a company that couldn't sponsor her
(07:46) How to find a workplace built differently
(13:39) Choosing remote work for the childhood she wanted
(14:55) Ruling out companies over the commute
(19:22) Being open about motherhood in interviews
(21:02) Why Heather refuses to carry the torch alone
(33:49) Advocating for her son like a sales leader
(36:34) How to build a community with other moms
(39:10) Save of the week

Connect with Mallory Lee: https://www.linkedin.com/in/mallorylee/

Connect with Shannon Curran: https://www.linkedin.com/in/shannon-sweeny-curran/

Connect with Heather Bell: https://www.linkedin.com/in/heatherbell-sales/

Check out Vector: https://vector.co

Produced in partnership with Share Your Genius

www.shareyourgenius.com

What are the baby and kid products that actually make motherhood easier, and which ones are just expensive things you thought you needed?

Mallory Lee and Shannon Curran swap their favorite parenting saves, from baby medicine baskets and stretchy pajamas to carriers, strollers, wagons, monitors, and the surprisingly valuable gift of an Uber Eats card. They share the products they kept reaching for, the purchases they would skip now, and the lessons they wish they had known before building a registry that cost thousands of dollars.

Throughout the conversation, they compare notes on baby gear, hand me downs, sleep struggles, kid technology, screen time, family calendars, and the everyday systems that help working moms keep things moving.

If you're a working mom, new parent, or simply trying to figure out what is actually worth buying for your family, this episode is a candid look at the favorite saves that earned their place in the house.

Jump into the conversation:

(00:00) Intro

(03:08) Building the perfect baby medicine basket

(04:58) The baby pajamas that actually last

(08:00) The traveling bassinet everyone shared

(11:44) The baby gear that becomes essential

(16:27) Finding what actually works for sleep

(19:43) Which strollers are really worth it

(25:22) The baby carrier worth every cent

(32:57) Raising kids with less screen time

(37:03) Family systems that make parenting easier

Connect with Mallory Lee: https://www.linkedin.com/in/mallorylee/

Connect with Shannon Curran: https://www.linkedin.com/in/shannon-sweeny-curran/

Produced in partnership with Share Your Genius

www.shareyourgenius.com