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How to Climb the Sales Career Ladder - Enterprise Edition -- with Craig Surgey

Closing Time: quick insights from sales & marketing experts

Release Date: 09/30/2024

Gaming LinkedIn for Sales? Authenticity Still Wins the Long Game -- with Tim Davidson show art Gaming LinkedIn for Sales? Authenticity Still Wins the Long Game -- with Tim Davidson

Closing Time: quick insights from sales & marketing experts

You saw the LinkedIn beef between Apollo.io and Seamless.ai—but did you catch that LinkedIn shut them both down? Media platforms hold the power, and if you want to keep playing the game, you’ve got to play by the rules. In this episode of Closing Time, we’re joined by Tim Davidson, founder of B2B Rizz, to unpack the risks of trying to game the LinkedIn algorithm. From automation flags to fake engagement tactics, Tim shares where people go wrong—and why authenticity is the long game that actually works. If you're serious about growing your B2B presence on LinkedIn without getting...

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The Right Way (and the Wrong Way) to Use AI in B2B Sales -- with Nick Caruso show art The Right Way (and the Wrong Way) to Use AI in B2B Sales -- with Nick Caruso

Closing Time: quick insights from sales & marketing experts

AI is transforming sales—but not everyone’s doing it right. In this episode of Closing Time, Nick Caruso, CRO at KnowledgeNet.ai, joins us to break down the smart (and not-so-smart) ways sales teams are using AI today. From AI SDRs and real-time lead research to bots talking to bots, Nick shares how to skip the gimmicks and use AI in B2B sales to drive real outcomes—not just activity. Whether you're playing catch-up or looking to level up, this is your shortcut to getting AI right in your B2B sales process. .   Want expert advice delivered monthly to your inbox? Subscribe to the...

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Power your Outbound Sales with These 7 Buying Signals -- with Jed Mahrle show art Power your Outbound Sales with These 7 Buying Signals -- with Jed Mahrle

Closing Time: quick insights from sales & marketing experts

Pipeline looking thin? Sitting back and hoping for inbound leads won’t cut it—not in today’s market. Top-performing reps know that building a predictable pipeline means getting smart about outbound. In this episode of Closing Time, Geoff Coutts sits down with Jed Mahrle, founder of PracticalProspecting.io, to break down seven buying signals that help reps reach the right prospects at the right time. Outbound will always be tough—but with Jed’s playbook, you’ll be miles ahead of anyone still doing it the old way. .   Want expert advice delivered monthly to your inbox? Subscribe...

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Beyond Cold Outreach: 4 Smarter (and Cheaper) Ways to Generate Pipeline -- with Sell Better's Chris Merrill show art Beyond Cold Outreach: 4 Smarter (and Cheaper) Ways to Generate Pipeline -- with Sell Better's Chris Merrill

Closing Time: quick insights from sales & marketing experts

Think cold calls and cold emails are your only shot at generating pipeline on a tight budget? Think again. In this episode of Closing Time, Chris Merrill, CEO of Better Media (the folks behind Sell Better & Market Better), shares tactical, low-cost strategies that go way beyond the inbox or the dialer. From live events and webinars to podcasting and building niche communities, Chris unpacks creative ways to drive demand—without draining your budget or your team. Whether you're a lean team, a startup, or just looking for smarter ways to generate pipeline, this episode is packed with ideas...

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Google’s New Ad Updates & How to Optimize Landing Pages for Higher ROI -- with Tas Bober show art Google’s New Ad Updates & How to Optimize Landing Pages for Higher ROI -- with Tas Bober

Closing Time: quick insights from sales & marketing experts

Hot off the Google press...if your landing page content doesn’t match your ad AND if it doesn't have navigation, your ad might not even get served (no matter how much you’re willing to pay). Google is officially emphasizing the importance of relevant content and easy-to-navigate landing pages.  In this episode of Closing Time, landing page expert and founder of The Scroll Lab, Tas Bober, breaks down what Google’s latest update means for marketers. She dives into why B2B and B2C landing pages should be structured differently, how to optimize landing pages for consumption before...

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B2B Influencers Are Here—How Marketers Can Leverage Them to Drive Results -- with Robyn Nissim show art B2B Influencers Are Here—How Marketers Can Leverage Them to Drive Results -- with Robyn Nissim

Closing Time: quick insights from sales & marketing experts

If you think influencers are just for B2C marketing, think again. B2B buyers are still people—and people trust people more than ads. Enter B2B influencers. In this episode of Closing Time, Robyn Nissim, founder of Social Proof Agency, breaks down why 2025 is the year of the B2B influencer. She shares how to find the right creators, structure partnerships for long-term impact, and measure success beyond vanity metrics. Whether you’re looking to build awareness or drive conversions, this conversation will change the way you think about influencer marketing in B2B. .   Want expert advice...

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

Closing Time: quick insights from sales & marketing experts

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....

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

Closing Time: quick insights from sales & marketing experts

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...

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

Closing Time: quick insights from sales & marketing experts

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. .   Want expert advice delivered monthly to your inbox? Subscribe to the Closing Time newsletter to never miss an episode: ...

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

Closing Time: quick insights from sales & marketing experts

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...

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More Episodes

You know you’ve arrived as a sales professional when you have repeatable business as an enterprise seller. Large deal sizes and a 7-figure W2…you’ve arrived.

How can you start your career off on the right foot to end up a successful enterprise seller? Is sales leadership your end goal?

In this episode of Closing Time, meet Craig Surgey, head of sales at Comtrade 360 and co-host of the Struggle Bubble podcast. He’s sharing his insights and the ways the sales career path has changed over time…and remained the same. If you’ve got enterprise dreams, this is the episode for you.

Watch the episode on YouTube.

 

Shopping for a new CRM? Get a demo or start a free trial of Insightly's modern CRM that teams love. 

 

Connect With: 

• Craig Surgey: LinkedIn //  Struggle Bubble podcast

• Val Riley: LinkedIn 

• Insightly: Instagram // Facebook // Twitter // LinkedIn // YouTube