Tailwind

John Buckner joins Tailwind for a practical conversation about prospecting, persistence, and why great work alone is not enough to grow a business: how owners need to keep surveying for new customers, why prospecting is really a process of choosing promising territory, how sellers can reframe rejection as yield, and why the people who keep digging are the ones most likely to find gold.

Tim Goering joins Tailwind for a practical conversation about AI, trust, and why human communication still matters in sales: how sellers can use AI as a tool without replacing real connection, why credibility, reliability, intimacy, and low self-orientation build trust, how phrases like "I understand" and "we help" can break equal business stature, and why expectation-setting, curiosity, practice, and real application turn sales concepts into better conversations.

Josh Shirley joins Tailwind for a practical conversation about building sales teams that treat business development as a core revenue engine: why BDR and SDR roles should not be treated like junior varsity sales work, how hunting and closing require different skills, why strong prospectors need a real path to growth, how closing-only cultures can stall when the market gets quiet, and why leaders should reward controllable prospecting behavior before the meeting ever gets booked.

Hamish Knox joins Tailwind for a practical conversation about building trust and consistency in sales: why rapport is different from relationship-building, how pattern interrupts make cold outreach feel more human, how going for the no and post-selling reduce ghosting, why older database leads are useful low-risk practice, and why leaders have to stay involved when a team is learning a new sales language.

Scott Bailey joins Tailwind for a practical conversation about sales process and Sandler behavior change: why winging it creates think-it-overs and ghosting, how going for the no produces clearer next steps, how post-selling can confirm commitments before they disappear, why old leads are a smart place to practice new techniques, and why leadership has to be involved if a sales team is going to change behavior.

Paul Doucet joins Tailwind for a practical conversation about cold calling as a modern pattern interrupt: why unexpected phone calls can still create real conversations, how disarming honesty removes pretense from outreach, how to decide who belongs in a cold call block, why the goal of the call is to book the next conversation, and how sellers can stay resilient through the nos without convincing themselves the phone does not work.

James Alberson joins Tailwind for a practical conversation about phone prospecting: why newer sellers often hide behind email, how mindset, behavior, and technique shape cold call success, why disarming honesty can release pressure at the start of a call, how live conversations build rapport faster than email chains, and why sellers should build multiple prospecting channels instead of relying on one outreach motion.

Dan Stalp joins Tailwind for a practical conversation about sales cookbooks and KPI tracking: why activity data should empower sellers instead of micromanage them, how simple hash marks can start the habit before CRM is perfect, how efficiency scores help teams reverse-engineer daily prospecting, and why consistent behavior matters when sales outcomes are naturally clumpy.

Robin Singh is President at Sandler Mississauga, where he helps sales teams use no-pressure prospecting, clearer cold call structure, and communication-style awareness to create better first conversations.

Matt Nettleton joins Tailwind for a practical conversation about outbound in an inbound world: why waiting for leads is not a sales strategy, how sellers can work backward from revenue goals into leading behaviors, why prospecting validates ICP and messaging, how teams should test voicemail and cold call approaches, and why person-to-person trust matters more as AI makes selling more efficient.