When Gui Costin sat down with Steve Benson on the Outside Sales Talk podcast, he delivered a masterclass in what it actually takes to build a high-performing, multigenerational sales organization - and keep it running. As the founder and CEO of Dakota, a firm that has helped clients raise over $40 billion in the investment services industry, Gui brings the kind of hard-won leadership wisdom that only comes from decades of building, breaking, and rebuilding sales culture from the ground up. What makes Gui Costin sales insights so compelling is that they cut against the grain of conventional sales…
AI SUMMARY • Summarize this article and recommended tools: ChatGPT ▶ Claude ▶ Grok ▶ Stop me if you've heard this one before… your best rep's pitch meeting went over, so now they’re late to their next meeting and stuck in traffic, watching a $50,000 deal slip away. Why? They planned their route the way they navigate to brunch - by casually using their phone’s default routing app. Here's the uncomfortable truth: most field sales teams bleed money via bad routing. How? They treat optimized routes with multiple stops like an inconsequential option, not a competitive advantage. Sales route…
Every industry and persona is different, but understanding how to sell to doctors takes particular nuance. When your target market - doctors, nurse practitioners, and PAs - put patient care first, success hinges on blending medical expertise with current digital realities: Like telehealth use in over 40% of visits and AI being adopted by healthcare orgs at 2.2x the rate of the rest of the economy. This guide, drawn from interviews with a primary care physician (who sees at least five reps a week!), a pharma specialist, an orthopedic device pro, and an animal health sales rep, distills timeless…
Wolf Cola, a regional beverage company, has been performing consistent and fair sales territory alignment for years - a lead comes in, that lead goes to Rep A. The next time a lead comes in, it is given to Rep B. The next lead goes to Rep C, and so on and so forth in a round-robin leads distribution process, safely logged in the related spreadsheet. Frank’s Fluids, a rival beverage company, also feel that they have a good handle on sales territory planning - they have four sales reps, each covering one of the four quadrants of the…
In yet another powerhouse interview, CEO Steve Benson hosts sales leadership veteran Alice Kemper, who reveals her "secret three actions" for sales managers aiming to hit quotas without the burnout. Drawing from 36 years of trailblazing - from teaching to managing dozens of reps at American Greetings - Kemper shares battle-tested tactics on coaching, analytics, and motivation. In this article, we've taken Kemper’s interview and boiled down her wisdom into five actionable insights, blending the core trio with ride-along extras and sales psychology gems, so you can implement them tomorrow. Afterwards, if you’d like to listen to the full…
When Gui Costin sat down with Steve Benson on the Outside Sales Talk podcast, he delivered a masterclass in what it actually takes to build a high-performing, multigenerational sales organization - and keep it running. As the founder and CEO of Dakota, a firm that has helped clients raise over $40 billion in the investment services industry, Gui brings the kind of hard-won leadership wisdom that only comes from decades of building, breaking, and rebuilding sales culture from the ground up. What makes Gui Costin sales insights so compelling is that they cut against the grain of conventional sales…
AI SUMMARY • Summarize this article and recommended tools: ChatGPT ▶ Claude ▶ Grok ▶ Stop me if you've heard this one before… your best rep's pitch meeting went over, so now they’re late to their next meeting and stuck in traffic, watching a $50,000 deal slip away. Why? They planned their route the way they navigate to brunch - by casually using their phone’s default routing app. Here's the uncomfortable truth: most field sales teams bleed money via bad routing. How? They treat optimized routes with multiple stops like an inconsequential option, not a competitive advantage. Sales route…
Every industry and persona is different, but understanding how to sell to doctors takes particular nuance. When your target market - doctors, nurse practitioners, and PAs - put patient care first, success hinges on blending medical expertise with current digital realities: Like telehealth use in over 40% of visits and AI being adopted by healthcare orgs at 2.2x the rate of the rest of the economy. This guide, drawn from interviews with a primary care physician (who sees at least five reps a week!), a pharma specialist, an orthopedic device pro, and an animal health sales rep, distills timeless…
Wolf Cola, a regional beverage company, has been performing consistent and fair sales territory alignment for years - a lead comes in, that lead goes to Rep A. The next time a lead comes in, it is given to Rep B. The next lead goes to Rep C, and so on and so forth in a round-robin leads distribution process, safely logged in the related spreadsheet. Frank’s Fluids, a rival beverage company, also feel that they have a good handle on sales territory planning - they have four sales reps, each covering one of the four quadrants of the…
In yet another powerhouse interview, CEO Steve Benson hosts sales leadership veteran Alice Kemper, who reveals her "secret three actions" for sales managers aiming to hit quotas without the burnout. Drawing from 36 years of trailblazing - from teaching to managing dozens of reps at American Greetings - Kemper shares battle-tested tactics on coaching, analytics, and motivation. In this article, we've taken Kemper’s interview and boiled down her wisdom into five actionable insights, blending the core trio with ride-along extras and sales psychology gems, so you can implement them tomorrow. Afterwards, if you’d like to listen to the full…
