Conversations with Women in Sales is a top podcast hosted by Lori Richardson. Every episode features a woman in sales who is doing incredible work, or an interview with a male ally, or conversation on a related topic. For the past 100+ episodes, guests share practical advice for advancing one's sales career. The podcast is dedicated to the memory of Barbara Giamanco, who founded CWWIS in 2018. Each episode features topics like: leadership, career management, dealing with imposter syndrome,…
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I met Jill when she was two years into her sales role at Hubspot. She visited the Women Sales Pros annual event at Simmons College in Boston and she was there representing Hubspot since no one else from Hubspot would stop by. Jill said, "uh, I'll come by" - and am I glad she did. It was the start of a great friendship that has lasted almost as long as she's been at Hubspot - we met 14 years ago.…
Need a dose of energy and enthusasm? Feeling down? Listen to and watch Women Sales Pros friend and ally, Dan Tyre, who joins the Conversations with Women in Sales podcast to talk about the most important aspects of becoming successful in sales or sales leadership - mindset and attitude. Dan champions mindset and his big goal now that he's been so successful in business is "Do More Good For the…
Tamar is the founder of eCore Services, a company she's bootstrapped and is celebrating six years in business with a team of 150 remote workers around the world. I've gotten to know Tamar this year, as she sponsored the #Salesdecadesproject as well as generously sponoring other women in sales and in business organizations. We talked about: Tamar shares her path from nonprofit work to becoming a…
Joanne Black is a 2026 Sales Decades Project Honoree. #SalesDecadesProject She celebrates 30 years running "No More Cold Calling" consulting, training, and coaching business. Joanne is open to connecting on LinkedIn - just make sure you customize the "ask" - say you heard about her on this podcast. Founder, No More Cold Calling Sales leaders often think they have a pipeline problem. More often,…
Maria Boulden got a degree in Chemical Engineering because she learned that a Chemical Engineer would be the highest paying engineering job possible. She was a rising star at Drexel University and landed a co-op role at DuPont while still in college. Since most of the sales roles were held by engineers back in the late 1990's / early 2000's it wasn't that hard of a transition when she landed her…
Lynn Hidy has been helping inside sales teams and sales leaders for years. Her new book, " Mastering Inside Sales Leadership: Your Get-It-Done Leadership Success Guide" is available January 8th. Lynn and I sat down to talk about sales leadership and career pathing in sales. More about Lynn: https://www.linkedin.com/in/lynnhidy/ Learn about her new book here:…
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…
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…
Hear some of our favorite takeaways from the following Conversations with Women in Sales guests: Jen Waltz Ayana Gardner Amber Hayes Ashley Wilson Kelly Hippler Cynthia Cross Erica Ettore Tracy Young Laura Lakhwara Dr. Jane Sojka Kayla Burke You can catch the FULL episodes of any of these snippets on iTunes or on Youtube - start by going to https://womensalespros.com/podcast/ We're on Youtube…
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…
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…
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…
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…
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…
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…
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 the past—are much less loyal to…
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…
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 -…
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…
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…
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…
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…
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:…
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…
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…
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 -…
Our goal at Women Sales Pros is to help support women in existing B2B sales roles to thrive, to get into leadership if they want to, and to recognize the companies and allies doing great things. This is a short episode with host Lori Richardson to cheer on 2025 and share resources like these ones: Find podcasts, women in sales organizations, and more here at Women Sales Pros -…
Ayana Gardner was recently named as one of "300 Women Making an Impact in B2B SaaS" so it is great that she kick off our first episode of 2025. Ayana is a ZCX Channel Leader at Zoom. We are also starting 2025 with our Q1 sponsor, RapidScale. Ayana has been in sales for a number of years and loves her current position which involves working with Zoom channel partners - a huge opportunity in B2B…
I always laugh about how so many women do wait to be tapped on the shoulder by a leader in the company to move into a different role - this did happen to Tania who began her career in her 20's in marketing. Tania now is a successful author, former corporate enterprise seller, and now runs Mindful Quadrant. We had a great conversation covering a lot of ground. Tania is working on a new version of…
When Elitsa and I spoke, we had many stories about competent women in sales and leadership roles who wait to get the "tap" on the shoulder to be promoted. Our male counterparts TELL their boss that they expect to be promoted many times and they initiate introductions with some of their C-level leaders, heads of other teams in their company and proudly state their accomplishments. Are we too shiy…
April Marks leveraged the communication skills she got in college to help her launch into a sales career - first as a BDR, then right into an Enterprise Sales role. She is currently at Pangea. My current role enables customers to leverage processes integrating API-based security services and strategically managing enterprise accounts, currently at Pangea. I am driven by the mission to streamline…
Kaivona Parker works with companies and individuals to help get more underserved folks into tech sales and support and champion them to success. We talked about the notion of people saying to bring your "whole self" to work, but in reality we can't all do that. Kaivona wants to help build up those in sales to help them grow and flourish. She trains, coaches, and is an all around sales enablement…
The book Ask Like an Auctioneer has a mission: to help 1 Million women ask for more and get it. But it's not just for women. It's for you if you want to: Get the raise of your life Land that partnership that can change everything Expand your influence in your domain Secure that whale of a client Refuse to lowball yourself Use asking as a success strategy I was thrilled to interview Dia because as…
Anna rose from inside sales support to a sales role at Oracle, to startup PlanGrid, then Autodesk (acquired PlanGrid) and now at TigerEye as VP of Sales. How did she do it? Anna is very conversational and I really enjoyed hearing her tips in doing well in sales and also what she has to say about AI. Listen to what she has to say about being a "lone wolf" and why you don't want to be that. Follow…
Do you know what you want in your career? Many of us know we don't like where we are at or our role, but we don't know what we DO want. Jaime Diglio's new book, "Moneyball Leadership" is not just for leaders - it is a quick read for anyone wanting to get out of the "war room" as Jaime puts it, and into the "win room". Mindset is so important in business - especially sales and sales leadership.…
My guest today is Sarah Gross, VP of Global Enablement at RingCentral. Sarah and I go way back, and most recently she became a new mom which has given her new perspectives about women and work. Sarah is also a top sales enablement professional who helps design process and support for sales teams like the ones at RingCentral. When Sarah and I first met, she was with Gartner, and has also worked at…
Brilliant business author Tamsen Webster has just released her newest book, Say What They Can't Unhear: The 9 Principles of Lasting Change. Tamsen describes the new book: The book is a compact and actionable guide that will get leaders (and others!) thinking differently about where change comes from and how to initiate it. By introducing and exploring nine "persuasion proverbs," I highlight the…
Her parents were Somali refugees who ended up in the U.K. As a child, Misky Sharif learned to be careful around the drugs and crime in her low income neighborhood. She rose above it, while learning as she grew up. How many kids would dodge all of the negative and find something positive in that? Listen as Misky explains how. Misky overcame obstacles and currently is in FinTech as an Account…
Now more than ever, we are seeing the importance of how sales fits in pre-sale and after the sale, and how sales needs enablement like the examples Deirdre offers are what helps grow . Learning, practicing, executing and coaching is the repeatable cadence Lori and Deirdre talk about creating "work life harmony" and the value of keeping in touch with those you've enjoyed working with previously. We…
Xactly is a tech platform for assisting companies with compensation and forecasting with the sales team, and has been around since 2005. They started sharing research about men in sales roles versus women in 2014 or so - quite some time ago, and just released their 2024 research results which includes the following: ● Representation disparities: The gender ratio in sales is alarming. Women are…
Gretchen launched Unbound and Unbothered, a career coaching business for women in tech in 2021. She helps high achievers who are stuck, stifled or at a crossroads ditch the stress and overwork to have a life and a job without burning out. Since she and I both got into tech in the "early days" (me earlier than her) we had a great conversation - I reference the title because we both worked for at…
"A billion dollar quota is like a 100K quota - you have to be comfortable talking about money with others" - one of the topics guest Marva Bailer and I bond on in our conversation shared today. I'm thrilled that our sponsor, Skillibrium, brings on advisors like Marva so that we can have real discussions around how to be successful. Marva was in sales before she learned how to drive - she and I…
Ashley Philipps is the author of the new book, The Teacher's Guide to Changing Careers . Being a former teacher myself, I am always up for hearing about others who left the admirable profession of teaching due to the lack of pay, and who got into sales roles. Ashley's book showcases other careers, but she did go into B2B sales and we talk about that on this episode. You will also hear my tip for…
I have known Michelle Benfer over the years and it was great to catch up with her in her role as SVP Sales, Business Line Owner at BILL. [Bill is (according to their website) the intelligent way to create and pay bills, send invoices, manage expenses, control budgets, and access the credit your business needs to grow—all on one platform.] Michelle is a sales leader and in our conversation we…
What is it like when two data focused people get together and talk? It does get a bit nerdy, but that's what I like about Sara, who lives in Stockholm, Sweden. Sara has been doing nearly all roles - from individual contributor - like SDR, BDR, AE and all the way up to VP and CRO. Now she is running two companies, "Break the Box" and "Skills." Like many of us who came from little money, Sara was…
We have had sales leader Gabrielle (GB) Blackwell on before (episode 85) and happy to have her back discussing some of her recent posting about toxic boss behavior in the sales workplace. GB and I were talking about more women than usual leaving B2B sales - something I am posting more about now as well. GB shares her story about some really unhealthy situations she's found herself in previously -…
How can you be in intergrity and hide part of your story? That was one of the big takeaways from my conversation with Jaime Konzelman, sales leader at tech company Rackspace. Jaime wrote a memoir called, "Dealmaker" that chronicles her life from college into exotic dancing and on into a stellar B2B sales career. Jaime has done big deals - hundreds of millions of dollars worth, at companies like…
When Meredith graduated from college, she taught English as a second language in Spain. She had graduated in 2011 and from Spain saw and heard that her friends back in the San Francisco Bay / Silicon Valley area were all getting tech jobs. Friends encourged her to hurry back and get on with a big tech company. Using her background as an NCAA varsity field hockey athlete, she walked into a sales…
If you have ever wanted bigger deals to build or to work on, you need to know our guest this episode, Dr. Barbara Weaver Smith. Having known Barbara for the last 10 or so years, I don't know why she hasn't been on the show sooner - and today she is talking about a new service she's launched utilizing generative AI, "Barbara AI" and the launch of her online Whale Hunters Institute. Barbara runs The…
It started for both Cherilynn and me by selling Girl Scout cookies. Like me, she LOVED selling cookies, and it seems to be one of the commonalities in our sales careers. Cherilynn Castleman wants to empower 1 million women for C-suite success by 2030! She is a force to be reckoned with - listen to our conversation and how we both want everyone to know how selling is really helping others. Learn…
