The #1 resource for top players in Tech Startup Sales. Hosted by Jesse Woodbury, an expert in early-stage startup selling, Sales Players features weekly, actionable ideas for reps, founders, and operators by exploring the mindset, skills, and tools high performers use to generate pipeline, close deals, and build wealth in Tech Sales.
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The podcast that helps sales reps and sales leaders emerge on purpose.
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Women Leaders on the Move - HerCsuite® Radio
Natalie Benamou, Host and HerCsuite® Founder, C-suite leader
Join Host Natalie Benamou, Founder of HerCsuite®, as she interviews women leaders who share business strategies for executives. Listen to the business podcast designed for executive women navigating board opportunities, growing businesses, and making meaningful career pivots. Featuring engaging conversations and actionable insights, each episode offers strategies to help women thrive professionally while embracing topics that matter most—including women's health, wellness, and personal growt ...
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Don't Miss Your Chance to Thrive in '25 with Erin Gallagher, Founder, Ella and The Hype Women's Movement
30:59
30:59
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30:59If you’ve been waiting for the right moment to step into what’s next—you just found it. Host Natalie Benamou is joined by Erin Gallagher, founder of Ella and the Hype Women Movement, who shares why Thrive in 2025 Women's Conference is unlike any event. Erin isn’t just delivering the keynote—she’s staying, engaging, and co-creating an immersive expe…
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What I Learned (the Hard Way) as a Founding AE
20:27
20:27
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20:27Jesse shares the unfiltered story of his time as the founding AE at a seed-stage startup. From landing the role on a mountain bike trail to building sales ops from scratch, it's a raw look at what early-stage startup life is really like. SPONSORS: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.co…
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Dream Bigger: Why Now Is the Time to Go All In, with Natalie Benamou, Founder, HerCsuite®
14:45
14:45
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14:45When was the last time you had an idea—but something stopped you? Maybe it was doubt, timing, or the belief that someone else was already doing it. Take a listen as Host Natalie Benamou, Founder of HerCsuite®, encourages you to reclaim your vision and imagine what’s possible—especially if you're in the second half of your career. This episode was i…
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This Is Exactly How I Approach Cold Calls Every Day
9:39
9:39
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9:39Jesse breaks down the exact cold call routine he uses daily to drive pipeline. SPONSORS: • ZoomInfo (The GTM Intelligence Platform) - Link for SP extended trial offer: https://try.zoominfo.com/sp EPISODE LINKS: • Want to get better at cold calls? Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNE…
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Jesse reminds sellers why understanding the product matters, especially when selling to IT buyers. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: •…
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Lessons Learned: Pivot Any Problem Into a Solution with Natalie Benamou, Founder, HerCsuite®
17:10
17:10
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17:10Have you ever thought something was too good to be true—but moved forward anyway? Ignoring your instincts happens to all of us—and what you do next matters most. Host Natalie Benamou shares real-world lessons from navigating major business challenges and how she turned setbacks into powerful solutions. As a lifelong problem solver, Natalie reveals …
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A Week in My Life: Tech Sales, Family, Fitness & Side Projects
17:48
17:48
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17:48Jesse shares a real-life look at how he juggles tech sales, content creation, fitness, and family life each week. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNEC…
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Why You're Still an SDR (and What to Do About It)
20:14
20:14
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20:14Jesse shares real strategies for SDRs looking to break into AE roles, drawing from his own journey from SDR > SDR Leader > Enterprise AE. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-…
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[Top Podcast Replay] 4 C-suite Strategies to Amplify Your Success with Dr. Ronicka Briscoe, Founder, Winning on the Road LLC
27:01
27:01
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27:01[Top Podcast Replay] What makes a great leader and how can you advance career while staying true to your values? In this insightful conversation, Dr. Ronicka Briscoe shares the strategies and mindset shifts that have helped her and women she interviewed step into high-impact leadership roles. Join Host Natalie Benamou as she talks with Dr. Briscoe,…
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Why You Should Hold Off on Going Fully Remote in Your Career
6:30
6:30
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6:30Jesse gives his take on why you should consider spending the first few years of your career in an office. SPONSORS: • Pre-Order Commission Impossible! - https://www.salesplayers.co/products/ci EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://ww…
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Why Now Is the Perfect Time to Launch Your Portfolio Career with Natalie Benamou, Founder, HerCsuite®
16:40
16:40
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16:40If you’ve been thinking, “I want more flexibility, but I still need financial security,” this episode is for you. Across every conversation with women leaders right now, one topic keeps coming up: portfolio careers. Whether you’re still in your corporate role, recently retired, or navigating a pivot, the idea of creating multiple income streams has…
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Comp Negotiation Fundamentals for Tech Sales
10:27
10:27
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10:27Jesse shares his basic process for negotiating compensation as a tech seller. SPONSORS: • Pre-Order Commission Impossible! - https://www.salesplayers.co/products/ci EPISODE LINKS: • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jessewoodbury/1-1-coaching-overview CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/in/jessewoodb…
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Key Mindset Shifts for Long-Term Success in Tech Sales
16:47
16:47
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16:47Jesse talks about mindset shifts sellers can embrace for long-term success. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Pre-Order Commission Impossible! - https://www.salesplayers.co/products/ci • Book FREE 1:1 Coaching Intro with Jesse: https://calendly.com/jes…
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Practical Advice for Starting a 7-Figure Business with Kym Insana Founder and CEO, AlwaysOn Digital
25:45
25:45
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25:45What if flexibility at work wasn’t a luxury—but the very thing that made your business successful? In this episode, host Natalie Benamou, Founder of HerCsuite®, talks with Kym Insana, a CEO who didn’t just build a 7-figure company—she built it around her life. After stepping away from a corporate career to raise her family, Kym knew she still wante…
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Why CEOs Need Grit — And How to Develop It with Aviva Leebow Wolmer, CEO Empower Leadership, LLC
20:25
20:25
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20:25Being a CEO requires more than just strategy and experience—it takes grit. The kind that gets you through uncertainty, setbacks, loneliness at the top, and the pressure to always have the answers. Take a listen to this conversation with Host Natalie Benamou and Aviva Leebow Wolmer, executive coach, Vistage Chair, and CEO of Empower Leadership LLC, …
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Jesse shares ideas for how you can become a more fierce competitor in your deals. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Mutual Action Plan: https://docs.google.com/pres…
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Using AI to Build The "R" in your CRM with Rachit Kataria of Centralize
49:08
49:08
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49:08Rachit Kataria is the Co-Founder & CEO of Centralize (https://www.usecentralize.com/) an all-in-one deal collaboration platform for enterprise revenue teams backed by Y Combinator. In this episode, Rachit shares his career story, the origins of Centralize, and the AI opportunity for Enterprise Sales. SPONSORS: • Surfe (LinkedIn Prospecting Streamli…
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AI Tools and Financial Strategies Every Entrepreneur Needs to Grow with Carlyn Bushman, CEO, CMB Brands, LLC
25:09
25:09
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25:09Are you always be launching or ready to always be learning? In this energizing episode of Women Leaders on the Move, host Natalie Benamou sits down with powerhouse entrepreneur and educator Carlyn Bushman to unpack what every service-based business owner needs to know right now. From using AI to build custom SOPs and track strategy KPIs to navigati…
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Dealing with Uncertain Times as a Tech Seller (& I Need YOUR Feedback)
16:16
16:16
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16:16Jesse shares how he is planning to navigate the uncertain times ahead and asks for feedback on what direction to take the show. Please reach out on Slack, InMail, or email [email protected] to share: #1 What keeps you coming back to the show? #2 What topics would you like to hear more about? For a few of you, I'll pay you for your time giving m…
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Here's How I Engage the Execs at My Top Accounts
10:16
10:16
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10:16Jesse shares the 10k play for developing a PoV when reaching out to executives at public companies. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Book FREE 1:1 Coaching Intro w…
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Your Next Board Seat is Closer Than You Think: Here's How You Get it with Natalie Benamou, Founder HerCsuite®
20:28
20:28
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20:28Do you know what the number one myth about landing a board position is? It’s the belief that you need to be in the C-suite to qualify. The truth is, you don’t need to be in the C-suite to land a corporate board. But here’s the catch: Many women struggle to navigate the board readiness process. The good news is, you’re not alone, and there’s a clear…
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Why It's Important to Find Your Niche in Tech Sales
15:54
15:54
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15:54Jesse shares thoughts on the current state of the market and some insights on the importance of finding a niche or specialization in your tech sales career. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/sal…
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Leading Innovation: How to Drive Change at Every Level with Robyn Bolton, Founder and Chief Navigator, Mile Zero
25:54
25:54
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25:54Innovation can feel like a leap into the unknown—especially when everything around us already feels uncertain. In this conversation, host Natalie Benamou talks with Robyn Bolton, Founder and Chief Navigator of Mile Zero and author of Unlocking Innovation. Robyn shares practical insights that make innovation feel more possible—and more urgent—than e…
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Improving Your Close Rate & Driving Predictability in Your Pipeline & Deals
25:34
25:34
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25:34Jesse shares a checklist of ideas for de-risking your deals to increase your close rate and drive more predictability in your pipeline and deals. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers E…
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How to Pick a Winning Startup as a Seller
29:52
29:52
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29:52Jesse shares some ideas for choosing a winning startup by drawing from his own experience working in early startups as a seller. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • B…
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Changing the Future of Women’s Heart Care with Dr. Simin Lee, Founder and CEO, Systole Health
29:15
29:15
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29:15Women’s heart health is often overlooked —but Dr. Simin Lee, board-certified cardiologist and CEO of Systole Health, is on a mission to change that. In this powerful episode of Women Leaders on the Move, host Natalie Benamou talks with Dr. Lee about the urgent need for better cardiac care for women, the power of group medical visits, and how she’s …
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Elevate Your Success By Focusing on Being with Megan Van Buiten, Co-Founder, People Conduit
23:38
23:38
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23:38What happens when we shift from always “doing” to simply “being” our authentic selves? Host Natalie Benamou sits down with her coach Megan Van Buiten, Co-Founder and Head of Mindset, Performance, and Leadership at People Conduit. Together, they explore how stepping away from the constant action of doing and instead focusing on being creates a power…
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How to Ace Sales Interviews & Be the Top Candidate
27:35
27:35
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27:35Jesse shares insights on the current state of tech sales hiring with ideas for how to ace your next interview. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/salesplayers EPISODE LINKS: • Book FREE 1:1 Coach…
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Get Unstuck and Thrive in 2025-We Believe in You with Jen Pestikas and Natalie Benamou
24:40
24:40
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24:40What if your next big career breakthrough wasn’t just a dream but a decision? In this episode, Natalie Benamou and Jen Pestikas take you behind the scenes of Thrive in 2025, a groundbreaking women’s leadership conference designed to help you move from feeling stuck to truly unstoppable. Unlike traditional events that leave you inspired but without …
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Lessons from the Startup Trenches with Amanda Crooks of BlinkMetrics
48:24
48:24
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48:24Amanda Crooks is the Founding Director of BlinkMetrics. In this episode, she joins Jesse to share lessons from selling software in a bootstrapped startup. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Promo link: https://www.surfe.com/?kfl_ln=jesse-woodbury • Fathom (#1 AI Notetaker) - SP Promo link: https://fathom.partnerlinks.io/sales…
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Break Free from Regret and Create Your Best Future LeeAnn Marie Webster, Speaker and Coach, Webster Enterprises
21:47
21:47
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21:47Every leader carries the weight of decisions past, but what if you could release those regrets and move forward empowered? In this transformative episode of Women Leaders on the Move, host Natalie Benamou welcomes LeeAnn Marie Webster, attorney, keynote speaker, and creator of the Regret Release Method. Discover how LeeAnn’s personal tragedy shaped…
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Finding Calm from Chaos using this 3C Formula with Natalie Benamou, Founder, HerCsuite®
19:46
19:46
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19:46Lately, life has felt like a whirlwind—so much change, so much uncertainty. You’re not imagining it. Women everywhere are feeling it too. But here’s the good news: You don’t have to navigate this alone. This episode is about shifting energy, finding your center, and reminding yourself that you have the power to feel grounded, supported, and uplifte…
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7 Tips for Getting the Most Out of Your Meeting Recording Tool
22:53
22:53
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22:53Jesse shares some tips for getting the most out of your sales meeting recordings tool (Gong, Chorus etc.) SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Discount link: https://www.surfe.com/?kfl_ln=jesse-woodbury EPISODE LINKS: • Get Fathom: Get Fathom: https://fathom.partnerlinks.io/salesplayers CONNECT WITH JESSE: • LinkedIn: https://w…
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Winning an Electric Car as a Sales Spiff and Other Crazy Career Stories with Chris Dankowski
55:18
55:18
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55:18Chris Dankowski is a Sales Strategy Consultant and Coach to Sellers and Founders in tech. Based in Austin, Texas, Chris has previously sold at top companies like: Evernote, Outreach and HubSpot. In this episode, Chris shares insights on managing your tech sales career. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Discount link: https:/…
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How to Prepare for Life’s Final Chapter with Cyndy Wulfsberg
34:38
34:38
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34:38At some point, we all face life’s final chapter—whether for a loved one or ourselves. It’s not easy to think about, but every leader will go through the transition. How are you ensuring peace of mind for the people you care about? In this episode of Women Leaders on the Move, host Natalie Benamou sits down with Cyndy Wulfsberg, author of Ghost or G…
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Why Your Buyers Don't Take You Seriously + Show Update & Re-Intro
32:13
32:13
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32:13Jesse shares an update on the future of Sales Players, re-introduces his background and shares an important mindset shift that will help your buyers take you more seriously. SPONSORS: • Surfe (LinkedIn Prospecting Streamlined) - SP Discount link: https://www.surfe.com/?kfl_ln=jesse-woodbury CONNECT WITH JESSE: • LinkedIn: https://www.linkedin.com/i…
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Leading with Purpose-Transform Your Business Into 'A Force For Good' with Coco Sellman
29:02
29:02
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29:02What does it take to build a business that thrives while also making a positive impact? In this episode of Women Leaders on the Move, host Natalie Benamou sits down with Coco Sellman, Founder and CEO of A Force For Good, entrepreneur, author, and advocate for purpose-driven businesses. They dive into the strategies that help leaders create sustaina…
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The Secret to Leadership Success: Prioritizing Your Well-Being with Irina Fursman
31:03
31:03
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31:03Are you prioritizing your health as a key asset in your leadership journey? This week on Women Leaders on the Move, host Natalie Benamou is joined by Irina Fursman, CEO and Executive Health Coach at Odysseys into Wellbeing, to explore how women leaders can transform their health into a strategic advantage. Chronic stress and overlooked health conce…
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Unlocking Limitless Leadership: Authenticity & Success with Natalie Benamou
21:12
21:12
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21:12Welcome to the 200th episode of Women Leaders on the Move. Today we are celebrating a milestone that is about so much more than numbers. This episode is about honoring you, our listeners, and the incredible journey we’ve shared. It’s about stepping into your light, being unapologetically you, and redefining what it means to be relevant as women in …
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Outcome of 7-Figure Deal: Increase in Customer Stock Price - Pod Swap with How the Deal Was Done
32:00
32:00
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32:00*Pod Swap - Jesse's interview on the How the Deal Was Done podcast: Jesse Woodbury shares his journey of converting a small proof of concept into a seven-figure deal with a B2C Home Services Company. A deal so impactful it raised the buying company’s share price. This deal is a perfect example of the power of internal champions and genuine customer…
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How Mara Smith Built a Women-Owned Tequila Brand from Scratch
22:23
22:23
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22:23Discover the ingredients of building a women-owned spirits brand in this episode of Women Leaders on the Move. Host Natalie Benamou sits down with Mara Smith, Founder and CEO of Inspiro Tequila, LLC, to discuss her extraordinary journey from corporate lawyer to visionary entrepreneur. Mara shares her story of redefining the spirits industry with an…
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From Burnout to Success: Leadership Lessons with Daisy Auger-Dominguez
28:20
28:20
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28:20How can leaders move from burnout to thriving while fostering collaboration and inspiring their teams? In this episode of Women Leaders on the Move, host Natalie Benamou speaks with Daisy Auger-Dominguez, author of Burnt Out to Lit Up: How to Reignite the Joy of Leading People. Together, they explore how leaders can recognize burnout, build trust, …
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Building Your Professional Network Via Slack with Kaela Altman of Salesforce, Salesblazers
48:26
48:26
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48:26Kaela Altman is the Community Manager for the Salesforce, Salesblazers sales networking community. Based in New York, she brings 15+ years of building, managing, and growing communities for enterprise tech. She joins the Sales Players to share details about growing and managing the Salesblazers Slack community. SPONSORS: • Leadfeeder (Turn Page Vie…
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How Color Psychology Can Transform Your Goals with Heather Eck
24:03
24:03
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24:03What if the colors around you could shape your energy, boost your creativity, and help you achieve your goals? Join us in this vibrant episode of "Women Leaders on the Move," where host Natalie Benamou talks with multimedia abstract artist Heather Eck about the transformative power of color. Heather shares her inspiring journey from a thriving corp…
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How to Build Generational Wealth: Smart Financial Strategies with Ruby "SunShine" Taylor
21:56
21:56
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21:56In this heartfelt and empowering interview host Natalie Benamou welcomes Ruby "SunShine" Taylor, the visionary founder of Financial Joy School, to discuss the profound impact of building generational wealth. Ruby’s journey, shaped by resilience and fueled by purpose, began after a traumatic brain injury and transformed into a mission to close the w…
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Becoming a Subject Matter Expert in Sales with Morgan J. Ingram
43:57
43:57
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43:57Morgan J. Ingram is the Founder & CEO of AMP Creative. Morgan is a force to be reckoned with in the B2B Sales Community. He initially gained traction as the creator and host of The SDR Chronicles and has since gone on to build an amazing career as a subject matter expert, keynote speaker and advisor. He joins the Sales Players to share how sellers …
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Why Women Leaders Must Lean In Now More Than Ever with Natalie Benamou, HerCsuite®
18:15
18:15
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18:15We are at the cusp of women stepping into our power. It all starts with the belief that we are living our most vibrant lives. Listen to host Natalie Benamou share her personal experience of leaning in and realizing that now more than ever women need to be comfortable being our authentic selves. Natalie shares her personal experience of self-doubt w…
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How to Use AI to Hit Your Goal in 2025 with Dustin Beaudoin of ChatAE
37:37
37:37
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37:37Dustin Beaudoin is the Founder of ChatAE, a copilot built for pre- and post-call tasks. Built to prep for calls, write recap emails, and plan next steps while coaching you to become an elite seller. Dustin joins SP to share ideas for leveraging AI in your sales process. SPONSORS: • Leadfeeder (Turn Page Views into Pipeline) - https://dash.partnerst…
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Redefining Success: How to Live and Lead with Purpose with Natalie Robinson
30:59
30:59
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30:59What happens when you align your purpose with your leadership values? Listen in to host Natalie Benamou as she talks with Natalie Robinson, an accomplished healthcare leader turned entrepreneur. Natalie Robinson shares her transformative journey from a high-powered career in the biotech and pharmaceutical industries to relocating her family to Tusc…
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How to Validate and Launch Your Next Big Idea with Elaina Zuke
23:15
23:15
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23:15Join host Natalie Benamou as she welcomes the remarkable Elaina Zuker, CEO of Elaina Zuker Associates, in an enlightening episode of "Mastering Influence." Elaina, an influence expert with over 20 years of experience, shares her journey from selling encyclopedias in Montreal to becoming a leading ad executive in New York. Discover how to assess new…
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