Tailwind

Nicole Vorkapic joins Tailwind for a conversation on hiring salespeople, defining the role clearly, and building a stronger ramp plan for new reps. We talk about why the job description needs to match the actual selling motion, how hunter and account management roles require different profiles, why small business owners should prioritize proven sales ability over deep product knowledge, and how the first 90 days should be managed with clear activity expectations, coaching, and accountability.

Troy Elmore joins Tailwind for a conversation on why prospecting initiatives fail and how sales leaders can make them stick. We talk about the three pillars of successful change — “I know, I care, and I can” — and why salespeople need a clear vision, a compelling reason, personal alignment, leadership commitment, skill development, coaching, accountability, and the right systems before they will consistently move outside their comfort zone and prospect for new business.Culture Build Success Matrix:https://topsail.app/downloads/tailwind/troy-elmore-leadership-commitment.pdf

Brian McDevitt joins Tailwind for a practical conversation about turning referrals into a consistent sales behavior. He explains why “introduction” is often a better word than “referral,” how specific names and relationship silos make the ask easier, when to ask for introductions, and why referrals can become one of the highest-leverage ways to build pipeline when sellers pair behavior, attitude, and technique.

Tom Daly joins Tailwind for a practical conversation about sharpening an ideal client profile, starting with customer pain, testing whether messaging resonates, excluding poor-fit prospects faster, and using sequences, landing pages, lead magnets, and automation once the target and message are clear.

Todd Twete joins Tailwind for a practical conversation about measuring prospecting from the top of the funnel down to revenue. He explains why the old three-touch idea has given way to an eight-touch average, how multichannel outreach changes conversion, why single-channel math can become unrealistic fast, and how leaders can swim upstream from revenue goals to see whether top-of-funnel activity supports the forecast.

Steve Cashdollar joins Tailwind for a practical conversation about the prospecting mistakes that keep sellers from standing out with today's buyer: weak personalization, too-fast calls to action, avoiding the phone, ignoring multichannel combos, slow follow-up cadence, and digital profiles that do not reinforce trust. He shares how authentic curiosity, buyer-centered questions, polite persistence, and equal business stature help sellers create conversations instead of noise.

Tim Roberts joins Tailwind for a practical conversation about moving beyond features-and-benefits selling: how pain hooks and pain parables help prospects recognize familiar business problems, why pattern interrupts and original thinking create curiosity, how leadership buy-in and repeated practice make sales training stick, and why psychological safety, permission to say no, and a learning mindset help sellers navigate buyer truth with equal business stature.

Judy Taibi joins Tailwind for a practical conversation about cookbook management and no-pressure prospecting: why sellers need a repeatable system, why behavior often matters more than attitude when activity has to happen, how pre-call planning and DISC communication can improve prospecting conversations, and how curiosity, permission, tonality, pattern interrupts, debriefing, and equal business stature help sellers create trust without pressure.

David Buonfiglio joins Tailwind for a practical conversation about turning smart, technical people into effective business development reps and recognizing the sales work inside more professional roles: how a documented playbook made intern prospecting more repeatable, why the BDR profile should match the buyer and complexity of the market, how a focused AI email template can make outreach more efficient without removing human review, and why consultants, lawyers, project managers, founders, and other professionals should see sales as part of the job rather than a separate identity.

Dan McCoy joins Tailwind for a practical conversation about AI, business development, and the return to more human prospecting: where AI helps salespeople prepare and organize, why AI-generated email and LinkedIn outreach is easier to ignore, how neutralizers and warm introductions improve opportunity quality, why network-building and consistent market presence matter, and how human review, intent, and relationship-building keep AI from flattening the sales message.