Tailwind

Lowell Price joins Tailwind for a conversation on strategic account prospecting and why the SDR playbook does not work the same way for complex enterprise accounts. We talk about the difference between volume-based outreach and account-based selling, why strategic AEs need to treat each target account as a “market of one,” how to select the right accounts, build multi-threaded relationships, use persona-based messaging, watch for compelling events, and why leaders need to support strategic sellers with strong ICP clarity, differentiated value propositions, coaching, tools, and account-level research habits.

Kenneth Gumbiner joins Tailwind for a conversation on value proposition, founder-led sales, and building a real sales operating system for small and midsize businesses. We talk about why many companies struggle because they cannot clearly explain the problem they solve, how value proposition connects to ICP, persona, messaging, profit, and process, why founders need to work on the business instead of staying trapped in day-to-day sales, and how the right playbook, CRM, reporting, client feedback, referrals, cold outreach, and buyer-intent signals help companies create consistent growth before they are forced to react to a lost client or missed quarter.

Roderick Jefferson joins Tailwind for a conversation on leadership, emotional intelligence, and how AI fits into the modern sales organization. We talk about the three-legged stool of IQ, EQ, and AI, why AI can provide content but still needs human context, how leaders can use AI as a business partner instead of just a research or writing tool, and why emotional intelligence, servant leadership, self-awareness, governance, and the ability to say “I don’t know” matter even more as technology moves faster.For more from Roderick, please visit:Stroke of Success Book: https://www.roderickjefferson.com/stroke-of-successSales 3.0 Book Link: https://roderickjefferson.com/bookSales 3.0 Companion Workbook: https://roderickjefferson.com/companion-workbook-sales-enablement-3-0Keynote Speaker Highlight Reel: https://bit.ly/3zRVNJaSocial Media Channels: https://linktr.ee/roderickjeffersonYouTube: https://www.youtube.com/@roderickjeffersonassociatesFree eBooks:Onboarding & EverboardingHarnessing Collective IntelligencePodcast Playlist (Spotify): http://bit.ly/4mHhSOv

Brent Phillips joins Tailwind for a conversation on networking, referrals, and why relationship-building is still one of the strongest business development channels. We talk about how networking creates trust transfer for fractional and small-business services, why corporate leaders should use networking as a low-cost way to learn and bring fresh ideas back into the business, how to get started even if networking feels uncomfortable, and why curiosity, generosity, clear positioning, consistent follow-up, and small referral partner groups can turn networking into a real growth engine.

Michael Wills joins Tailwind for a conversation on founder-led sales, sales infrastructure, and why prospecting breaks down when leadership has not clearly defined the strategy. We talk about the “go with God and come back with money” approach that leaves reps guessing, why ICP definition is a leadership responsibility, how founders can recognize when they have hit the founder-led sales ceiling, and why strong sales organizations need strategy, structure, process, tools, people, clear incentives, weekly operating rhythms, roleplay, and KPIs that measure progress toward the right kind of revenue.

Joe joins Tailwind for a conversation on cold calling, prospecting mindset, and how to keep the prospect’s guard from going up the second they answer the phone. We talk about why bad prospecting does not prove prospecting is dead, how to combine calls, voicemail, email, and LinkedIn into a real system, why the goal of a prospecting call is not to sell but to uncover a problem and book a meeting, and how pattern interrupts, curiosity, tonality, third-party stories, and a no-pressure next step can make cold calls feel more human and more effective.

Lisa Mulyk joins Tailwind for a conversation on AI, sales fundamentals, and how leaders should adopt new tools without losing judgment, human connection, or common sense. We talk about why AI should be treated as a tool rather than a replacement, how overreliance can weaken basic skills, where AI can create real efficiency in research and preparation, why companies need clear AI policies and governance, and why the fundamentals of communication, critical thinking, soft skills, and change management matter even more as the technology moves quickly.

Doug Dvorak joins Tailwind for a conversation on AI, professional selling, and how sales teams can use new technology without losing the human side of the work. We talk about how AI is changing sales operations, research, coaching, and revenue efficiency, why leaders should start by exploring the AI tools already inside their CRM and marketing platforms, how to keep sellers focused on high-value conversations, and why salespeople should treat AI as the next layer of professional literacy rather than something to fear.AI and the Future of Professional Salese-Book: https://topsail.app/downloads/tailwind/doug-dvorak-ai-future-professional-selling.pdfAudio Book: https://firebasestorage.googleapis.com/v0/b/topsailrevenue.firebasestorage.app/o/tailwind%2Fdoug-dvorak-ai-future-professional-selling-audiobook.mp3?alt=media&token=fdba51f7-b030-4532-9b70-85805e2cf155

Phil Whitebloom joins Tailwind for a conversation on objection handling and why objections should be treated as clues instead of roadblocks. We talk about how objections often reveal something important that was missed earlier in discovery, why sellers should acknowledge, question, validate, and then respond instead of getting defensive, how to identify red herrings, and why asking better follow-up questions can protect margin, uncover the real issue, and keep the conversation moving forward.

Glenn Nixon joins Tailwind for a conversation on ICP discipline, ICP degradation, and why not all revenue is created equal. We talk about how growing sales teams need to translate the ideal customer profile into clear operational filters, why leaders have to explain the “why” behind those boundaries, how saying yes to near-fit opportunities can erode margin and focus, and why sales leaders need to reinforce ICP through questions, CRM fields, scorecards, compensation, coaching, and accountability.