Podcast artwork thumbnail for Win Win Podcast

Win Win Podcast

Riley Rogers

Booking Overview

A business interview show focused on workplace trends, sales enablement, and go-to-market practices, typically featuring working professionals who share firsthand experience from their organizations. Credible pitches include sales enablement and GTM leaders with practical expertise in seller training, buyer engagement, tool adoption, or applying AI to sales workflows; booking difficulty is low, as guests are experienced practitioners rather than high-profile public figures.

Metrics

Episodes: 156

Frequency: Weekly

Rating: 4.9/5.0

Estimated listeners: 100 - 1,000

Listener location: USA

YouTube: 1.4k subscribers

Page updated: Oct 28, 2026 · How we check this data

Contact Information

Publicly listed emails

community@highspot.com

Looking for the right person? Join Podseeker to find direct host and producer contacts and manage your podcast outreach.

Host

Riley Rogers - Host of a show exploring workplace trends and practical approaches to navigating them successfully.

Booking Intelligence

Booking Requirements

low
Typical Credentials:  
Experienced practitioners or leaders in sales enablement, go-to-market, sales, or related business functions who can share practical examples from their organization.
Required Achievements:  
Leadership or specialist experience in sales enablement or go-to-market functions, Hands-on work improving sales training, buyer engagement, or tool adoption, Practical experience navigating business or technology change

Recent Guest Discussions

Rebecca Sharbono - Supporting Sellers Through Organizational Change And Enabling Go-to-market Teams Amid Rapid Ai-driven Transformation.

Julia Townsend - Building Agile Go-to-market Enablement And Developing Skills As Products And Markets Evolve.

Tommy Dauphin - Personalization, Buyer Engagement, And Ways To Earn Attention In Modern Sales Outreach.

Molly Donlon - Personalization, Buyer Engagement, And Ways To Earn Attention In Modern Sales Outreach.

Ryan Costello - Embedding Enablement Into Sales Tools And Improving Tool Adoption For Go-to-market Teams.

Recent Topics

Business, Sales, Sales Enablement, Go To Market Strategy, Artificial Intelligence

Episodes

Here's the recent few episodes on
Win Win Podcast
:

Episode 160: Supporting Sellers Through Monumental Change

September 18, 2026

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 much always the same: move quickly, keep the field informed, and make sure what they’re armed with is 100% accurate. So how do you bu...

Episode 159: Outpacing the Market with Agile GTM Enablement

September 10, 2026

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 asking the same question: what does it actually look like to build an enablement and a go-to-market model that...

Episode 158: Bringing a Human Touch to GTM Workflows

September 04, 2026

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 does it actually look like to show up in a way that earns a buyer’s attention? Riley Rogers: Welcome to the Win/Win Podcast. I’m your host, ...

Frequently asked questions

Here's some frequently asked questions for
Win Win Podcast
:

How do I get in touch with Win Win Podcast?

Win Win Podcast is hosted by Riley Rogers. Its publicly listed email is community@highspot.com. For guest bookings, the host or producer is usually the best person to reach. Podseeker helps you find direct host and producer contacts and pitch from your own inbox.

What is the email for Win Win Podcast?

The publicly listed email for Win Win Podcast: community@highspot.com.

How many listeners does Win Win Podcast have?

Podseeker estimates Win Win Podcast reaches 100 to 1,000 listeners per episode. Only the publisher has exact numbers.

Who is an ideal guest for Win Win Podcast?

Win Win Podcast typically books working professionals with real expertise. Typical guest background: Experienced practitioners or leaders in sales enablement, go-to-market, sales, or related business functions who can share practical examples from their organization. Common among recent guests: Leadership or specialist experience in sales enablement or go-to-market functions; Hands-on work improving sales training, buyer engagement, or tool adoption; Practical experience navigating business or technology change. Recent guests include Rebecca Sharbono, Julia Townsend, and Tommy Dauphin.

How hard is it to get booked on Win Win Podcast?

Low. A guest with relevant expertise and a clear angle for its audience has a realistic chance.

What topics does Win Win Podcast cover?

Recent episodes cover Business, Sales, Sales Enablement, Go To Market Strategy, and Artificial Intelligence. Pitch an idea tied to one of these topics and mention a recent episode.

How does Podseeker get this information?

From public sources and our own research: podcast websites, social profiles, podcast feeds, and our data team. Podcast feeds and episodes are checked daily, and details like contacts, recent guests, and booking difficulty are refreshed regularly.

I host Win Win Podcast. How do I correct this page?

If something here is out of date, ask us to correct it through Podseeker's contact form at podseeker.co/contact. Our research team reviews every request and updates the listing.

Publicly listed emails

community@highspot.com

Looking for the right person? Join Podseeker to find direct host and producer contacts and manage your podcast outreach.

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