Sessions
NAWBO Chicago is thrilled to provide the attendees of Women Mean Business®: NAWBO Chicago’s Regional Entrepreneurial Conference & 42nd Annual Fundraiser high quality educational sessions throughout the day. Please see below for a list (alphabetical order by presenting company or organization) of sessions and their descriptions.
Women And Wealth: The Strength Of Women Investors: 9:00 – 10:00 am, Kent Room
Sponsored By: Tryline Private Wealth of the Princeton Group
Speaker: Jeffrey Simon
Women investors are increasingly taking on important roles in managing their family’s finances. We will address the unique challenges and strengths faced by women as they look for opportunities to improve their financial health and become more empowered. We will cover how you can build, manage, protect and enjoy your wealth with confidence.
15 Tips To Help Your Business Thrive
Sponsored By: Tryline Private Wealth of the Princeton Group
Speaker: Jackie Pilossoph
Fresh off the release of her latest book, Who Let the Dogs Out, Jackie Pilossoph cleverly compares the people we meet in the business world to dog breeds. Get ready for lots of laughter, along with the inspiration she hopes will help your business continue to thrive.
Sales Tax and Small Business – Why Should I Care?: 9:00 – 10:00 am, York Room
Sponsored By: Yetter Tax
Speaker: Diane Yetter
If you’re selling anything—whether it’s clothing, food, consulting services, digital subscriptions or handmade crafts—you might be considered a “retailer” in the eyes of state tax authorities. And that could mean you’re on the hook for collecting sales tax—not just in your home state, but possibly across the U.S., and even internationally. Why is this happening? As states face reduced federal funding, they’re relying more and more on sales tax. That means expanding who has to collect it and what kinds of products and services are taxable. Since the 2018 U.S. Supreme Court decision in South Dakota v. Wayfair, the rules around sales tax have completely shifted. Now, you can be required to collect tax even without a physical presence in a state—thanks to what’s called economic nexus. And on top of that, many states are now taxing digital goods and services, too. Whether you sell through your own site, on Amazon or Etsy, or offer services and digital content, you could be impacted. Join national sales tax expert Diane Yetter of Yetter Tax to break down what all this means in plain English. You’ll walk away with practical tips to help you understand your obligations and stay compliant—without getting overwhelmed.
Learning Objectives:
- Learn how to determine when you need to register to collect sales tax
- Understand the differences between physical nexus and economic nexus
- Discover situations where you may not need to register, even if you have nexus
- Get clarity on what goods, services and digital products might be taxable
- Know the difference between direct selling vs selling through marketplaces like Amazon, Etsy or eBay
Scaling With Intention: Lessons From Growing A 7-Figure Firm: 9:00 – 10:00 am, Hunt Room
Sponsored By: Justworks
Speakers: Sophia Pietrkowski and Jaime Staley
(L-R: Sophia Pietrkowski and Jaime Staley)
What does it really take to build a thriving business that aligns with your values, your lifestyle and your long-term vision? In this session, Sophia Pietrkowski, Account Executive with Justworks, and Jaime Staley, co-founder of Willow Virtual CFO, will participate in a fireside chat offering lessons learned from growing a fully virtual, 7-figure financial services firm — with transparency, intention and a whole lot of learning along the way. But this isn’t just about one firm’s journey. It’s about equipping you with insights you can use — whether you’re in the early stages of business or actively scaling. From mindset shifts to team building, pricing strategies to systems that support sustainable growth, you’ll walk away with practical takeaways and inspiration to grow your business on your terms. This session is ideal for women entrepreneurs who want to scale without sacrificing purpose, presence or people in the process.
Getting to the Next Level: Women Breaking Barriers and Building Legacies: 10:30 – 11:30 am, Kent Room
Sponsored By: BBV Wealth Management Group of Merrill Lynch
Speakers: Karen Coley, CEO of SBC Waste Solutions Inc., Cathe Evans-Williams, Managing Attorney at the Evans Williams Law Group, LLC and moderated by Gladys Castillo, Small Business Performance Manager at Bank of America.
(L-R: Karen Coley, Cathe Evans-Williams and Gladys Castillo)
This dynamic panel brings together trailblazing women who’ve shattered glass ceilings, redefined success on their own terms, and turned challenges into steppingstones. These women business owners will share real stories of ambition, resilience, and the power of self-belief. And how a strong relationship with your advisor and banker can unlock growth, reduce stress, and create lasting financial success. Whether you are launching your own venture or navigating change during these times, this conversation will equip you with the insights, tools, and inspiration to get to your next level.
Crafting Your Company’s Financial Narrative: 10:30 – 11:30 am, York Room
Sponsored By: Bisi Blvd
Speaker: Noelle Curtis
Every business tells a story—make sure yours is one of clarity and growth. This hands-on workshop helps entrepreneurs craft their unique financial narrative using essential metrics, break-even analysis, and forecasting tools. Learn how to set goals, track what matters and speak confidently about your numbers to funders, partners or your team. You’ll leave with a refined financial story and strategies to drive business success. Bisi Blvd tools will be introduced to support your ongoing financial management.
The LemonAd Effect: Refreshing Your Brand to Stand Out and Succeed: 10:30 – 11:30 am, Hunt Room
Sponsored By: Verizon Digital Ready
Speakers: Vanessa and Calvin Jackson
(L-R: Vanessa Jackson and Calvin Jackson)
This workshop is designed to revitalize your brand’s identity and market presence. Drawing inspiration from The LemonAd Stand’s innovative approach to creative marketing, this session will equip you with practical strategies to enhance your brand’s appeal and distinguish it from competitors. Learn how to infuse creativity into your marketing efforts, effectively communicate your unique value proposition, and foster a strong connection with your target audience. Elevate your brand and ensure lasting success in today’s competitive landscape.
Key takeaways:
1. Defining Your Differentiators
2. Building Your Brand Identity
3. Implementing & Evolving Your Brand
Spotlight On Success: Insights To Grow Your Business: 11:45 am – 1:30 pm, Grand Ballroom
A Panel Featuring the 2025 NAWBO Chicago Award Winners
Join the entire NAWBO Chicago community for one of the most inspiring sessions of the conference — “Spotlight On Success: Insights To Grow Your Business,” where we shine a spotlight on extraordinary women business owners who are not only making waves in their industries but also giving back in meaningful ways through their involvement with NAWBO Chicago.
The panel discussion during the lunch portion of Women Mean Business® will feature the 2025 award winners: Anabel Lopez for Member of the Year, Jessica Freiburg for Women Business Owner of the Year, Brooke Foley for the Visionary Award, Laurette Rondenet for the Visionary Award and Qiana Turner for Young Entrepreneur of the Year.
These trailblazers will share their journeys, lessons learned and the values that drive both their business success and their commitment to lifting others. From overcoming challenges to creating lasting impact, this panel is a celebration of leadership, service and the power of women supporting women. Don’t miss this powerful conversation with some of the most dynamic voices in our community!
Key HR Compliance Issues Every Employer Needs to Know: 2:00 – 3:00 pm, Kent Room
Sponsored By: Miller Cooper & Co., Ltd
Speakers: Angela Adams and Sue Winkler
(L-R: Angela Adams and Sue Winkler)
Good HR is just good business. Especially with the many challenges employers face with the people-side of their business, and new regulations that seem to surface each year. Keeping up and protecting your business has become more complicated than ever. Join Sue Winkler, Director of Client HR Services, and Angela Adams, HR Consulting Manager, from Miller Cooper & Co., as they review critical compliance issues and best practices that you should be aware of.
Topics and key takeaways include:
- Understanding key compliance issues:
-Worker and employee classification
-FLSA and Wage and Hour requirements
-Paid leave obligations
-Pay transparency impact
-Employee files and documentation best practices - Common blind spots to uncover
- Tips to overcome the pain points
Even if you have just one employee, this is a session you do not want to miss.
Drop Some H.E.A.T.: How to Make a Big Impact With Your Marketing on a Small Budget: 2:00 – 3:00 pm, York Room
Sponsored By: Supporting Strategies | Northern Chicago & Supporting Strategies | Chicago Southland
Speaker: Alan Stern
Drop Some H.E.A.T. is Alan Stern’s signature keynote designed to help salespeople and business owners stay top of mind in a fun, authentic and cost-free way. Using the H.E.A.T. Method – Humor, Education, Adding Value and Trust – Alan provides a simple framework for building a personal brand that allows people to naturally warm up to you over time.
This engaging presentation highlights a key truth: before people buy from a brand, they buy from a person who represents a brand. Alan demonstrates how to create memorable connections by delivering value, showing personality and earning trust on a shoestring budget. Attendees will walk away with practical strategies to amplify their presence, strengthen relationships and position themselves as relatable and reliable leaders in their fields.
Bold Voice, Big Impact: How To Be An Advocate For Your Business: 2:00 – 3:00 pm, Hunt Room
Sponsored By: Athena Law Group
Speakers: NAWBO Chicago Advocacy Committee Co-Chairs Diana Leza Sheehan and Stephanie Posey
(L-R: Diana Leza Sheehan and Stephanie Posey)
In a time when women’s voices are being challenged, your business cannot afford for yours to be silent. Join the NAWBO Chicago Advocacy Committee for this high-impact, one-hour session created for female founders who are ready to stand up, speak out and lead with purpose. You’ll learn how to confidently advocate for your business — whether it’s claiming your value, shaping local policy or telling your story in powerful ways. This is more than a workshop; it’s a call to action. Now is the time to raise your voice—not just for your business, but for the future of NAWBO women in entrepreneurship.
From Manual to Magical: Unlocking AI for Everyday Business Operations: 3:15 – 4:15 pm, Kent Room
Sponsored By: Cumberland Irving
Speaker: Danielle Green
Discover how AI can be a game-changer for your small business. In this interactive session, we’ll dive into practical ways business owners can harness the power of artificial intelligence to boost efficiency, cut costs and elevate the customer experience. From automating repetitive tasks to enhancing team communication and optimizing inventory, you’ll learn how AI can simplify your operations and give you a competitive edge in today’s fast-paced market. Whether you’re just starting to explore AI or looking to expand your toolkit, this workshop will provide real-world insights you can apply immediately.
Dare to Delegate And Grow Your Company: 3:15 – 4:15 pm, York Room
Sponsored By: BridgePoint Technologies
Speaker: Sue Harrawood
“Can I give this to someone else to do?” / “I double booked again. My calendar is a mess.” / “Where is that important email from my client? My inbox is a disaster.” / “I’m working so hard. How come I don’t have money for things I want to do?” / “I forgot to send the invoices out again. I am so tired of no cashflow. Should I hire a bookkeeper?” / “When do people find the time to send out a newsletter AND post on social media? Maybe they have someone do it for them. How much does that cost?” / “I can probably do it better myself and besides, I don’t have the time to train someone.”
Sound familiar? How many times have you had one or more of these conversations in your mind as your business grows? Y-O-U are not alone. Delegation is the key to success of growing businesses. Whether the right fit for your company is a full-time or part-time employee or a Virtual Assistant, there are great future team members out there for you. Join us as we brainstorm and drill down on what you can delegate, what level of experience you need, which kind of team member is the right fit for you (FT/PT employee, Virtual Assistant contractor), how much time it takes to find and train, and more.
Taming The Crazy: An Optimized Approach To Perimenopause And Menopause For Successful Women: 3:15 – 4:15 pm, Hunt Room
Sponsored By: Old National Bank
Speaker: Dr. Dominika M. Hertsberg, DC, ECS, DipACLM
As a lifestyle medicine provider, Harvard trained nutrition expert, entrepreneur, and a late blooming mother, Dr. Hertsberg helps women feel, look, and perform better at every stage of their lives. In this presentation and discussion, she will share her optimized approach to managing the physical, emotional, and professional challenges during the transitional phases of perimenopause and menopause. Dr. Hertsberg will discuss practical tips for enhancing energy, mitigating symptoms of estrogen deprivation, and maintaining productivity at home and at work. She will highlight how her expertise in biooptimization, nutrition, and tech-assisted fitness can empower attendees to embrace this transformative period. Attendees will have the opportunity to ask questions and exchange stories with Dr. Hertsberg.
