Closing Time: quick insights from sales & marketing experts

Insightly
  • 5.0 (3)
  • MARKETING
  • UPDATED WEEKLY
Closing Time: quick insights from sales & marketing experts

Closing Time is a weekly podcast with insider tips and insights for go-to-market leaders. In each episode, you’ll meet a luminary in the sales, marketing, or customer success field and get actionable tips and tactics to elevate your game. Each 15-minute episode will go deep on skills to close deals, see the latest on marketing tech, or check out trends to elevate the customer experience.

  1. Why “Connect-to-Market” is the New “Go-to-Market” -- with Casey Cheshire

    1 HR. AGO

    Why “Connect-to-Market” is the New “Go-to-Market” -- with Casey Cheshire

    Are you truly connected to your customers? Too many marketers think they know their buyers—but can you name seven of your customers by first and last name? If not, you might be suffering from disconnected marketing. In this episode of Closing Time, host Val Riley sits down with Casey Cheshire, Chief Evangelist at Ringmaster Conversational Marketing, to discuss why go-to-market needs to become connect-to-market. Casey points to three areas where you should be making better connections with your audiences: Partnerships, Community, and Podcasting. Stop assuming what your customers want. Instead, connect with them and ask. Learn how in this episode. Watch the episode on YouTube.   Want expert advice delivered monthly to your inbox? Subscribe to the Closing Time newsletter to never miss an episode: https://bit.ly/3C5aZUw   Connect With:  • Casey Cheshire: LinkedIn // Ringmaster   • Val Riley: LinkedIn  • Insightly: Website // Facebook // Twitter // LinkedIn // YouTube

    14 min
  2. Stop the Excuses! How to Master Outbound Sales in 2025 -- with Troy Munson

    FEB 24

    Stop the Excuses! How to Master Outbound Sales in 2025 -- with Troy Munson

    It’s cold season—cold calling, that is. And while we’re at it, let’s toss in cold emails too. If you’re a sales rep waiting around for inbound leads to magically appear, you’re leaving money on the table. It's time to prioritize cold outreach in 2025. “But no one answers the phone anymore!”—hogwash! Meet Troy Munson, CEO of Dimmo and proud cold-caller. In this episode of Closing Time, he breaks down how cold calling actually works in a post-pandemic, remote-first world—if you’ve got the right tools and mindset. Plus, he shares cold email and social selling strategies to help you cut through the noise and book more meetings. Watch the episode on YouTube.   Want expert advice delivered monthly to your inbox? Subscribe to the Closing Time newsletter to never miss an episode: https://bit.ly/3C5aZUw   Connect With:  • Troy Munson: LinkedIn // Dimmo  • Geoff Coutts: LinkedIn  • Insightly: Website // Facebook // Twitter // LinkedIn // YouTube

    15 min
  3. How to Hire a Fractional CMO (And What to Expect) -- with Andrew Dod

    FEB 17

    How to Hire a Fractional CMO (And What to Expect) -- with Andrew Dod

    Hiring a Chief Marketing Officer (CMO) is a big commitment—especially for growing companies that may not have the budget for a full-time executive. That’s where fractional CMOs come in. A fractional CMO provides high-level marketing leadership without the full-time price tag. But how do you find the right fit for your business? Andrew Dod, an experienced SaaS marketing leader and fractional CMO, shares what companies should consider before making this hire. Watch the episode on YouTube.   Want expert advice delivered monthly to your inbox? Subscribe to the Closing Time newsletter to never miss an episode: https://bit.ly/3C5aZUw   Connect With:  • Andrew Dod: LinkedIn // qmarq  • Val Riley: LinkedIn  • Insightly: Website // Facebook // Twitter // LinkedIn // YouTube

    14 min
  4. How to Manage Your Sales Pipeline Like a President’s Club Seller -- with 30mpc's Nick Cegelski

    FEB 3

    How to Manage Your Sales Pipeline Like a President’s Club Seller -- with 30mpc's Nick Cegelski

    A messy pipeline doesn’t just frustrate your sales leader—it kills deals. When sellers don’t have a clear picture of where each opportunity stands, they waste time chasing the wrong prospects, struggle to forecast accurately, and ultimately lose revenue. So why isn’t pipeline hygiene every team’s top priority? Because it takes time, discipline, and a little help from our friends at 30 Minutes to President's Club. In this episode of Closing Time, Insightly SVP Geoff Coutts welcomes Nick Cegelski, Founder of 30mpc, to share actionable strategies to manage your sales pipeline like a president's club seller. Nick provides practical (daily) tips to help your sales org stay on top of pipeline hygiene—and win more deals because of it. Download your copy of the Insightly x 30mpc guide: https://www.insightly.com/30mpc/   Watch the episode on YouTube.   Want expert advice delivered monthly to your inbox? Subscribe to the Closing Time newsletter to never miss an episode: https://bit.ly/3C5aZUw   Connect With:  • Nick Cegelski: LinkedIn // 30 Minutes to President's Club  • Geoff Coutts: LinkedIn  • Insightly: Website // Facebook // Twitter // LinkedIn // YouTube

    20 min
  5. How (And When) to Hire a Marketing Agency vs. In-house -- with Brianna Doe

    JAN 27

    How (And When) to Hire a Marketing Agency vs. In-house -- with Brianna Doe

    Hiring your first marketing agency? Get prepared now. In this episode of Closing Time, we break down everything you need to know before making the leap—like when it’s the right time to bring on outside help, how to choose between full-service or boutique agencies, and the key questions you should ask during the selection process. What’s the tipping point for outsourcing? How can you ensure the agency’s communication style aligns with your team? And most importantly, how will you measure their impact? Get all the answers (and more) with expert advice from Brianna Doe, founder of Verbatim and host of the Stop the Scroll podcast. Watch the episode on YouTube.   Want expert advice delivered monthly to your inbox? Subscribe to the Closing Time newsletter to never miss an episode: https://bit.ly/3C5aZUw   Connect With:  • Brianna Doe: LinkedIn // Verbatim agency  • Val Riley: LinkedIn  • Insightly: Website // Facebook // Twitter // LinkedIn // YouTube

    15 min
  6. Discounting Dangers: How to Keep Deals Moving Without Discounting in B2B Sales

    JAN 20

    Discounting Dangers: How to Keep Deals Moving Without Discounting in B2B Sales

    Discounting in B2B sales is one of the quickest ways to erode trust and credibility—so why does it happen so often? In this episode of Closing Time, John Barrows, CEO of JB Sales Training and author of I Want to Be in Sales When I Grow Up, breaks down why proactive discounts often do more harm than good, how they devalue your offering, and why they signal to buyers that your pricing isn’t credible. John also shares actionable strategies for keeping deals moving without relying on discounts, from leveraging creativity and flexibility to building value during discovery. Plus, he unpacks how to handle the infamous “procurement wildcard” and what every rep needs to know about their company’s pricing strategy to close deals confidently. Watch the episode on YouTube.   Want expert advice delivered monthly to your inbox? Subscribe to the Closing Time newsletter to never miss an episode: https://bit.ly/3C5aZUw   Connect With:  • John Barrows: Instagram // LinkedIn // John's Sales Training & Resources  • Val Riley: LinkedIn  • Insightly: Website // Facebook // Twitter // LinkedIn // YouTube

    24 min
  7. Lights, Camera, Sell: Finding Success with Video Prospecting in 2025 (Plus Tips From Improv Comedy) -- with Chris Bogue

    JAN 13

    Lights, Camera, Sell: Finding Success with Video Prospecting in 2025 (Plus Tips From Improv Comedy) -- with Chris Bogue

    Still waving a whiteboard in desperation on your sales videos? Or kicking off with a screen share in your intro? Let’s leave those habits in 2024. Chris Bogue, sales coach and author of The Complete Guide to Selling on Video, believes video is a goldmine for storytelling and connection—if done right. In this episode of Closing Time, Chris shares actionable tips for mastering video prospecting in 2025 using lessons from his side hustle: improv comedy. Learn how to take what you’re given, present your point of view with confidence, and use your prospect’s values and goals to create videos that don’t just stand out—they convert. Watch the episode on YouTube.   Want expert advice delivered monthly to your inbox? Subscribe to the Closing Time newsletter to never miss an episode: https://bit.ly/3C5aZUw   Connect With:  • Chris Bogue: LinkedIn // Download the The Complete Guide to Selling on Video  • Val Riley: LinkedIn  • Insightly: Instagram // Facebook // Twitter // LinkedIn // YouTube

    19 min
  8. How to Get SaaS Pricing Right (and What Most Companies Get Wrong) -- with Bill Wilson

    JAN 6

    How to Get SaaS Pricing Right (and What Most Companies Get Wrong) -- with Bill Wilson

    Pricing a SaaS offering is probably the hardest issue most leadership teams will tackle. In this episode of Closing Time, we sit down with Bill Wilson, founder and CEO of Pace Pricing, a B2B SaaS pricing consultancy. Bill brings his expertise to unpack the complexities of SaaS pricing, from determining who within an organization should own pricing decisions to common mistakes companies make—and how to avoid them. Bill also dives into actionable strategies for creating a pricing page that resonates with your audience, builds trust, and drives conversions. Plus, he explores how to leverage a freemium model to fuel product-led growth, including the critical role of delivering value quickly and efficiently. Watch the episode on YouTube.   Want expert advice delivered monthly to your inbox? Subscribe to the Closing Time newsletter to never miss an episode: https://bit.ly/3C5aZUw   Connect With:  • Bill Wilson: LinkedIn // Pace Pricing website // Pricing page scorecard • Val Riley: LinkedIn  • Insightly: Instagram // Facebook // Twitter // LinkedIn // YouTube

    21 min
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5
out of 5
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About

Closing Time is a weekly podcast with insider tips and insights for go-to-market leaders. In each episode, you’ll meet a luminary in the sales, marketing, or customer success field and get actionable tips and tactics to elevate your game. Each 15-minute episode will go deep on skills to close deals, see the latest on marketing tech, or check out trends to elevate the customer experience.

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