Episode 519 – Carole Mahoney, Darryl Praill, and Tim Hughes
Meet
Carole Mahoney
Carole Mahoney has been called the “Sales Therapist” by a Harvard Business School professor. As the founder of Unbound Growth, she coaches Harvard Business School Entrepreneurial MBA students on sales, is a top sales influencer, a Woman to Watch in Sales by Sales Hacker, and a recognized sales coach helping organizations improve prospecting and business development performance.
Darryl Praill
Darryl Praill is the Chief Revenue Officer at VanillaSoft, the industry’s most established Sales Engagement Platform. He is an award-winning marketer, Sales World Top 50 Keynote Speaker, SaaS branding expert, social media influencer, podcaster, and serial entrepreneur. Darryl has raised nearly $100 million in venture capital, taken companies public, led acquisitions and mergers, and built high-growth revenue organizations.
Tim Hughes
Tim Hughes is universally recognized as one of the world’s leading pioneers of Social Selling and has consistently been ranked among the most influential social selling experts globally. He is the Co-Founder and CEO of DLA Ignite and co-author of the bestselling books Social Selling – Techniques to Influence Buyers and Changemakers and Smarketing – How To Achieve Competitive Advantage through Blended Sales and Marketing.
Our Mission Is To Change The Negative Perception Of Sales People
Our Vision Is A World Where Selling Is A Profession To Be Proud Of
Sales prospecting and lead generation are the lifeblood of any thriving sales career—but they’re also some of the most misunderstood and mismanaged aspects of the job. Carole Mahoney, Darryl Praill, and Tim Hughes share insights that challenge traditional mindsets and equip listeners to approach prospecting with precision, empathy, and creativity.
We explore the necessity of ongoing learning, time-blocking for prospecting, and seeking support from peers. My experts also discuss the risks of overvaluing a single champion in the sales cycle and the power of humanized content to generate authentic engagement on social media.
Outline of This Episode
- [04:59] Improving email outreach strategy
- [09:15] Losing an unexpected deal
- [12:34] Effective social networking strategies
- [16:21] Finding out all about your client’s why
- [18:56] Using social media prospecting
- [20:29] Humanizing content for prospecting
Cadence Creativity & Customer-Centric Outreach
Carol Mahoney discusses her take on the essentials of prospecting. Her first commandment: never “set it and forget it” with your outreach cadences—every sequence deserves refinement. She cautions against careless copy-paste errors and the classic mistake of making outreach messages too self-focused, stressing the power of speaking to the customer’s problems and industry context.
Carol’s checklist encourages iteration, reflection, and resilience. She also shares a story of transforming a client’s cold email from company-centric to customer-driven, resulting in nearly double the response rate. Her closing advice is a real golden nugget: “keep it brief, keep it about them, and always aim for meaningful, smaller asks.”
Mastering Mindset
Darryl Praill names learning, time-blocking, and asking for help as the top habits of high-performing prospectors. He refuses to accept excuses and warns against putting all your eggs (and hopes) in one champion’s basket when navigating complex sales. Darryl addresses the overlooked art of asking for referrals and the pitfall of undervaluing yourself in conversations. He shares a one of his sales low points when overconfidence blinded him to the broader decision-making team—an experience that underscores his golden rule: map the whole account and never stop multi-threading your relationships.
Connection & the Human Touch
Tim Hughes digs into the art of creating buyer-centric social profiles and building a network that truly remembers you. His three do’s: a relevant profile, genuine network growth, and memorable, strategic content. He draws a sharp line against “social spamming”—pitching immediately after connecting on LinkedIn—and instead champions authentic relationship building.
Tim gives practical advice, from using a real, distinctive profile photo to writing a “why-driven” summary that sparks curiosity. He shares how a single, heartfelt LinkedIn post about his teammate’s personal experience generated thousands of views, C-level conversations, and closed deals.
Connect with Carole Mahoney
Connect with Darryl Praill
Connect with Tim Hughes
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