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Episode 160: Supporting Sellers Through Monumental Change
Podcast
Episode 160: Supporting Sellers Through Monumental Change
According to Gartner, sales organizations undergo an average of four transformations every two years. Of those, only 11% manage to drive commercial success. For the go-to-market organization, and especially for the enablement function within it, that statistic says a lot. Every single one of those transformations lands on their desk, and the ask is pretty […]
18 min read
Episode 159: Outpacing the Market with Agile GTM Enablement
Podcast
Episode 159: Outpacing the Market with Agile GTM Enablement
According to LinkedIn’s Workplace Learning Report, 49% of L&D professionals say their executives are concerned that employees don’t have the right skills to execute their business strategy. And in busy, fast-paced industries, that gap is becoming a real problem. Because if the product, market, and go-to-market motion are all evolving at once, organizations are left […]
21 min read
Episode 158: Bringing a Human Touch to GTM Workflows
Podcast
Episode 158: Bringing a Human Touch to GTM Workflows
According to Gartner, 73% of B2B buyers actively avoid suppliers who send irrelevant outreach. That tells us two things. One, personalization is prolific. Many teams are trialing different plays and finding varying degrees of success. Two, personalization is a risky play. Get it wrong, and you might actually do more harm than good. So what […]
24 min read
Episode 157: Embedding GTM Enablement into Every AI Tool
Podcast
Episode 157: Embedding GTM Enablement into Every AI Tool
According to Salesforce’s State of Sales Report, sales teams use an average of 10 tools to close a deal, which then leaves 66% of reps to say that they’re overwhelmed by the sheer number of platforms they’re expected to juggle in their day-to-day. So when an enablement team goes to roll out new tools, reps […]
22 min read
Episode 155: Shaping Strategy with Deal Intelligence
Podcast
Episode 155: Shaping Strategy with Deal Intelligence
According to research by Gartner, by 2029, sales organizations with AI-driven enablement functions will achieve 40% faster sales stage velocity than those using more traditional approaches. But getting there means building the kind of workflows that tell you what actually works, which is only possible when you can see inside the conversations that selling actually […]
21 min read
Episode 154: Turning Skepticism Into Enthusiasm for a New Platform
Podcast
Episode 154: Turning Skepticism Into Enthusiasm for a New Platform
According to Salesforce, sales professionals spend up to 40% of their time searching for the information and knowledge they need to do their jobs. For go-to-market teams stretched across multiple products, multiple acquired businesses, and a sprawling tech stack, that number can feel like a conservative estimate. So how does a solo enabler cut through […]
22 min read
Episode 153: Decoding the “Build or Buy?” Question from the IT Perspective
Podcast
Episode 153: Decoding the “Build or Buy?” Question from the IT Perspective
According to Gartner, at least 30% of generative AI projects will be abandoned after proof of concept due to escalating costs, poor data quality, or unclear business value. There are a lot of factors working against them, and too often failure happens when teams are right in the middle of building. They’ve spent significant time, […]
23 min read
Episode 152: Upleveling Execution Through Practical AI Application
Podcast
Episode 152: Upleveling Execution Through Practical AI Application
According to research by IBM, just 16% of AI initiatives have achieved scale. Why? Because few organizations have the structure and data to support long-term AI investments. So, how do you build an AI-ready system? Riley Rogers: Welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends […]
23 min read
Episode 151: Designing Deal-Winning Buyer Experiences
Podcast
Episode 151: Designing Deal-Winning Buyer Experiences
According to Corporate Visions, 74% of buyers say they faced too many competing options in their last major purchase decision, and instead of selecting a vendor, they just checked out entirely, gave up, and moved on. So, how do you create a buying experience that makes those decisions feel easy? Riley Rogers: Hi, and welcome […]
28 min read
Episode 150: Enabling Sellers to Show Up as Trusted Partners in Every Deal
Podcast
Episode 150: Enabling Sellers to Show Up as Trusted Partners in Every Deal
According to research by Salesforce, 86% of business buyers are more likely to buy if companies understand their goals, and nowhere is that statistic truer than in the nonprofit sector. So, how do you ensure that your sellers are ready to show up the right way for every buyer?  Riley Rogers: Hi, and welcome to […]
28 min read
Episode 149: Transforming Strategy into Real-World Execution
Podcast
Episode 149: Transforming Strategy into Real-World Execution
According to research by Gartner, 84% of business leaders report their company’s identity must significantly change to achieve strategic objectives. But how do you know when the time is right? And more importantly, how do you ensure that change goes smoothly? Riley Rogers: Welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive […]
18 min read
Episode 148: Delivering High-Impact Enablement as a Team of One
Podcast
Episode 148: Delivering High-Impact Enablement as a Team of One
According to Highspot’s Go-To-Market Gap Report, 98% of leaders say their GTM strategy is active, but only 10% see it driving results. The reason for that? Strategy abounds. Real meaningful execution, not so much. So how do you overcome the go-to-market performance gap and bridge that growing rift between strategy and execution? RR: Hi, and […]
23 min read
Episode 147: Winning in a Distributor-led Sales Environment
Podcast
Episode 147: Winning in a Distributor-led Sales Environment
According to research from Promotional Products Association International, the promotional products industry is digitizing, and it is digitizing fast. Last year, online sales represented 25% of total industry sales, which is a 19% increase year over year. As the industry shifts, promotional product organizations like Polyconcept North America are as well. So, how do you […]
21 min read
Episode 146: Connecting Rep Behavior to Proven Business Outcomes
Podcast
Episode 146: Connecting Rep Behavior to Proven Business Outcomes
According to research by G2, organizations with a sales enablement strategy achieve, on average, a 49% higher win rate on forecasted deals. But to see these kinds of returns, you first need to get sellers, leaders, and the business itself bought into the value of enablement. So, how do you build confidence in the function’s […]
24 min read
Episode 145: Building Alignment With Intentional Infrastructure
Podcast
Episode 145: Building Alignment With Intentional Infrastructure
Research shows that sales professionals at aligned companies are more than twice as likely to exceed their goals than those misaligned companies. So, how do you build an aligned company that prepares marketing and sales teams to work together and win together? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley […]
17 min read
Episode 144: Leading Sales Through AI Transformation
Podcast
Episode 144: Leading Sales Through AI Transformation
According to research by Gartner, 70% of sellers are overwhelmed by the number of technologies required to do their work, and 72% are overwhelmed by the number of skills required for their roles. Put simply: It’s tough out there.  So, how do we create systems that make it easy for sellers to work and, more […]
22 min read
Episode 143: Measuring Marketing Performance in B2B Manufacturing
Podcast
Episode 143: Measuring Marketing Performance in B2B Manufacturing
According to research by Forrester, when brand experience and customer experience are improved together, companies can achieve up to 3.5x revenue growth. So how do you build a trusted brand all while consistently delivering high quality customer experiences?  Riley Rogers: Hi, and welcome to the Win/Win podcast. I’m your host, Riley Rogers. Join us as […]
25 min read
Episode 142: Designing Enablement for Scale in Healthcare
Podcast
Episode 142: Designing Enablement for Scale in Healthcare
According to research from the State of Sales Enablement Report 2025, businesses with well-integrated enablement tech stacks are 42% more likely to increase sales productivity. So, how do you go about building an effective, well integrated tech stack? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as […]
22 min read
Episode 141: Designing Curated Enablement Experiences
Podcast
Episode 141: Designing Curated Enablement Experiences
According to research on organizational alignment led by LSA Global highly aligned companies grow revenue 58% faster and are 72% more profitable than misaligned companies. So how can you cultivate an aligned culture ready to drive improved outcomes?  Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as […]
16 min read
Episode 140: Creating Clarity in a Complex Sales Environment
Podcast
Episode 140: Creating Clarity in a Complex Sales Environment
According to the State of Sales Enablement 2025 Report, 20% of organizations see the sales process as a key strategic priority. So how can you optimize your sales process and drive higher win rates for your team? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we […]
13 min read
Episode 139: Strengthening Agency Partnerships Through Enablement
Podcast
Episode 139: Strengthening Agency Partnerships Through Enablement
According to the State of Sales Enablement Report, 2025, 29% of companies still rely on multiple disconnected GTM tools. So how can organizations leverage a unified platform to scale sales readiness and achieve GTM success? Riley Rogers: Hi, and welcome to the Win/Win Podcast. I’m your host, Riley Rogers. Join us as we dive into […]
18 min read
Episode 138: Developing a Reliable, Repeatable Launch Process
Podcast
Episode 138: Developing a Reliable, Repeatable Launch Process
According to Forbes, sales reps spend 35.2% of their time selling and 65% of their time on literally everything else. So how can organizations cut through the noise and focus reps on the activities that matter most? Riley Rogers: Hi, and welcome to the Win-Win Podcast. I’m your host, Riley Rogers. Join us as we […]
17 min read
Episode 137: Unlocking the Value of Content Through Effective Governance
Podcast
Episode 137: Unlocking the Value of Content Through Effective Governance
According to research from Forrester, 70% of marketing content goes unused. So how can you effectively structure and govern your content to unlock its value and drive measurable business results? Riley Rogers: Hi, and welcome to the Win-Win podcast. I’m your host, Riley Rogers. Join us as we dive into changing trends in the workplace […]
13 min read
Episode 136: Bridging the Gap Between GTM Strategy and Execution
Podcast
Episode 136: Bridging the Gap Between GTM Strategy and Execution
According to the GTM Performance Gap Report, 98% of leaders say their GTM strategy is active, but only 10% see it driving results. So how can organizations bridge this gap and turn strategy into meaningful execution that drives outcomes? Riley Rogers: Hi, and welcome to the Winland Podcast. I’m your host, Riley Rogers. Join us […]
18 min read
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