Conversations with Women in Sales

Episode 212 here, with a great sales leader named Shay Keeler, VP of Sales at Common Room.

Shay spent 4-1/2 years at Outreach, starting as an Account Exec and getting promotions throughout her stay there. Now she is at Common Room as VP of Sales. We talked about her meteoric rise in various organizations - what it takes to get a promotion into a new role or one you've never done before, and how selling is different in the age of AI...

Jaime Diglio and I have a lot in common when it comes to our beliefs for success in sales. 

Mindset is where it's at - first and formost. Jaime created a program that takes you from your "WAR" room in your head into you "WIN" room. 

She agrees that the most important first sales conversation is the one you have with yourself. 

Are you down and need a boost? Listen to this episode and we'll cover tips and ideas to help you get into ...

It is an amazing new book: "Women and Power: Your Guidebook to Risk, Resilience, and Confidence" by U of Cincinnati sales and marketing professor Dr. Jane Sojka released in August, 2025.  It's all about ways women can rise within a B2B sales career - and it happens to be good for men, too - and really anyone who wants to be more successful with their ideas, goals, and plans. 

There are four parts to the book: 

Part 1: Self-Limiting...

Kelley and I had a great conversation about her sales career - some of the highlights below: 

As a seasoned Chief Revenue Officer with over 20 years of global commercial leadership experience, Kelley specializes in driving sustainable revenue growth and transforming sales organizations.

She is a strategic, data-driven, people-first leader committed to achieving challenging goals through thoughtful planning, relentless execution, an...

I had such a wonderful conversation with Channel Sales Leader and Mentor Jen Waltz. 

As Chief Information Security Officer of Imagenative, Jen is: 

FOUNDER and CISO. Empowering Your Business to Scale, Secure and Succeed.

She helps with:
Cybersecurity and Emerging Technologies: Help partners build, deliver, and manage cutting-edge cybersecurity solutions.

Enterprise IT & Digital Transformation: Adopt next-gen technology solutions b...

Listen to Ashley Wilson, Co-Founder of Momentum and the great conversation that happened.  We talked about her career journey from sales and marketing to co-founder status.

We also talked about the adoption of AI and how things are changing. For years, in sales we had trouble with the data that lives in conversations on sales calls and in written form has long been left out of crucial follow up by reps. 

AI is here to help sellers ...

Nhungly Dang and I had a great conversation around what four careers her parents expected her to do, and how she found her way into business and ultimately leading SDR and BDR teams to great success. Now she leads PipeVisionIQ as a consultant after more than 12 years building front line sales teams. 

Nhungly has developed SDR workflows that are data-driven, technology-driven and adaptable to any organization's environment.

✅ She h...

Laura Lakhwara leads GTM teams and customers in transformative strategies that empower businesses to streamline operations and scale efficiently with AI, automation, robotics, and data-driven insights.

She has an incredible background from working at IBM, a first-ever partnership with IBM and Apple, and other companies like UI Path and Softbank Robotics. 

We had a great conversation - her expertise spans market entry strategies, en...

I had a great conversation with co-author of the new book, "The Activator Advantage"'s Karen Freeman. Here is some information about the book from DCM Insights: 

There is a growing problem in the professional services industry that is often acknowledged but rarely discussed openly: clients—even long-standing ones for whom firms have delivered unquestioned value in t...

Tracy Young has been on our radar for some time, having co-founded PlanGrid (acquired by Autodesk) and now co-founder of TigerEye - a GTM modern analytics platform. As a successful co-founder, Tracy has a natural sales background combined with her engineer background - a powerful combination. 

On the TigerEye website, the company's core values are: Wholehearted, Humility, Kaizen, Trust, and Simplicity. Tracy discusses how she leads...

Erica has helped build a global team at Workiva where everyone has a "me vs. me" mentality - working to improve ourlseves, not a competitive "me versus you" attitude. How can you get better? How can you deliver the best to your clients and internal consitutents. 

Erica was named "Manager of the Year" and she says it is because of her incredible team. 

We talked about holding people accountable - such an important issue for leaders ...

Amber Hayes is currently Director of Sales at a Toronto company called Voices, which is the #1 marketplace for voice-over. We had a great conversation about how you need to pivot and embrace change within your company so that it doesn't outgrow you. 

She started at Voices as a Project Administrator, and listen to the episode to learn more about her move to sales, and now sales leadership. Amber is in her 11th year at Voices - unusu...

The time has come where we hit 200 episodes and it was a pleasure to have on good friend and "Sales Energizer" Alice Heiman. Alice also hosts a great podcast called Sales Talk for CEOs. 

We need to keep talking about more women in sales and sales leadership since we still have huge opportunities for more women in sales and sales leadership. 

Alice and Lori talk about the last ten years of effort to help create inclusive B2B sales t...

Cynthia Cross was all set for a career in accounting when she went to college. A wise professor suggested she would not like that major and encouraged her to do something else where she could utilize her social skills and outgoing personality more. Upon graduation she moved to Wichita, Kansas and met a sales manager who encouraged her to get into a sales role. 

Cynthia says the throughline in her entire career has been who she know...

Katie McDonald was in sales previously. Now she coaches women in self-care because of so many of us who have gotten burned out or just put ourselves last. Hear some of Katie's suggestions for your crazy busy life. She talks about "ME management" 

It's all about self-care strategies because the fact is most of us are running on fumes and we're borrowing future energy to get through today. Katie wants to disrupt that. Wh...

Sarah Kiley has had a sales caree where she's risen through the ranks.  She's built a reputation for aligning people, processes, and technology to deliver measurable outcomes. Whether it's launching new products, driving cross-functional collaboration, or spearheading strategic initiatives, she has focused on creating value for customers, partners, and stakeholders alike.

More about Sarah: https://www.linkedin.com/in/sarahkiley/

Samantha Craig wanted to be a teacher. She got through school but then had a hard time finding a job. She knew she loved to travel so she wondered if she could travel somewhere and teach. 

Sam ended up teaching for a year in South Korea. 

She came back to her home state of Massachusetts and realized she wanted to teach somewhere else so set off for Washington, DC. 

At some point Sam considered a job "until she got her teaching job"...

Kayla Burke is an Enterprise Sales Specialist at Microsoft and Founder of "The Tech Level" helping others to get a tech sales role. 

When Kayla graduated from college she became a business analyst but found that it didn't bring her much joy in her job. A random person told her about sales hiring going on at IBM and she ended up becoming a Business Development Manager - and has loved technology sales ever since. 

In addition to bein...

I first met Andrea Sittig-Rolf in the early 2000's - we had both recently launched our B2B sales consulting businesses and she was about to get her first of several books published.  Fast forward to now, and she has a 22 year track record of success in helping thousands of sellers and hundreds of companies with the "top of funnel" prospecting part of professional selling. 

More about Andrea: 

2021 - 2024 CRN Woman of the Channel. T...