Music major? Waiter? Hotel clerk? They might not sound like typical stepping stones to a successful sales career—but they absolutely can be. While some reps follow the traditional path (business degree → SDR → AE), there’s no one-size-fits-all blueprint for thriving in sales.

In fact, some of the best sales pros come from the most unexpected backgrounds. In this episode of Closing Time, meet Lindsey Boggs—go-to-market advisor and former opera major—who turned stage presence into sales excellence. She shares how nontraditional experience can translate into sales success, and what sales leaders should look for when hiring B2B sales reps from unconventional backgrounds.

Watch the episode on YouTube.

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Connect With: 

• Lindsey Boggs: LinkedIn // LFB Consulting

• Insightly's Website // Unbounce's Website // LeadsRx's Website 

The North American economy is uncertain, so what should your agency be doing to stay profitable and keep growing? In this episode of Closing Time, we sit down with Jon Morris, founder of Fiscal Advocate, a firm that helps marketing agencies make smarter financial decisions through real planning—not just bookkeeping.

Jon shares the offensive and defensive strategies every agency should be using to navigate today’s unpredictable market. From identifying what’s really stalling growth to maximizing cash flow and investing wisely, this conversation is packed with insights to help agency owners weather the storm and come out stronger on the other side.

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: 

• Jon Morris: LinkedIn // Fiscal Advocate

• Val Riley: LinkedIn 

• Insightly's Website // Unbounce's Website // LeadsRx's Website 

Email fatigue is real—and it’s hitting B2B marketers hard in 2025. With inboxes flooded by AI-generated outreach, outdated content, and automation overload, it’s no wonder open rates are tanking. So what can you do to stand out and stay relevant?

In this episode of Closing Time, we’re joined by Jack Kosakowski, CEO of Creation Agency (U.S.), who shares 7 practical tips to revive your marketing email nurture strategy. From smarter segmentation to more tactical content and tech stack hacks, this episode is packed with actionable ideas to help you build emails people actually want to open. Your email list is a competitive advantage—if you treat it like one.

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: 

• Jack Kosakowski: LinkedIn // Creation Agency

• Val Riley: LinkedIn 

• Insightly's Website // Unbounce's Website // LeadsRx's Website 

Do you know the scroll rate or the engagement rate on your landing pages and website? Google does, and they are using those metrics to determine how you show up in search results.

In this episode of Closing Time, Jennifer Denney of Elevated Marketing Solutions talks about the key metrics on your website and landing pages, and how improving them can lead to an improved user experience, lower cost-per-click, and more visibility in search.

Plus, she unpacks Google’s latest update and what it really means for marketers trying to get more from their paid media campaigns.

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: 

• Jennifer Denney: LinkedIn // Elevated Marketing Solutions

• Val Riley: LinkedIn 

• Insightly's Website // Unbounce's Website // LeadsRx's Website 

Product-led growth thrives when customers can explore, try, and succeed—without ever needing to talk to sales. But designing that seamless, self-serve experience? That’s the hard part.

In this episode of Closing Time, Geoff Coutts sits down with Dave Boyce, Executive Chair and EVP of Product at Winning by Design, to explore how AI is transforming the PLG motion. From AI-guided demos and onboarding to post-sale copilots and intelligent product recommendations, they discuss how AI can fill in the gaps where human support once lived.

Dave also shares why the “self-service happy path” is essential for any PLG strategy—and what product leaders need to build before layering in AI. If you’re looking to scale more efficiently and put more power in your users’ hands, this one’s for you.

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: 

• Dave Boyce: LinkedIn // Winning by Design 

• Geoff Coutts: LinkedIn 

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

How do you know if LinkedIn is really influencing your pipeline? Val Riley sits down with Deivis Rupslaukis, founder of DERU Digital, to explore practical ways to track LinkedIn ad impact—from adding “How did you hear about us?” to your forms, to manually cross-referencing CRM data, to using attribution tools like LeadsRx.

Plus, Deivis shares a clever workaround for LinkedIn’s lack of impression capping—and why showing your ads to the same accounts might be tanking your results. If you're spending time and budget on LinkedIn, this episode is for you.

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: 

• Deivis Rupslaukis: LinkedIn // DERU Digital, B2B paid media agency 

• Val Riley: LinkedIn 

• Insightly's Website // Unbounce's Website // LeadsRx's Website 

What really drives a customer to click, convert, and come back?

This week on Closing Time, we’re joined by Jon MacDonald—founder of The Good and author of Behind the Click—to explore the psychology behind every stage of the customer journey.

From mental shortcuts to mobile optimization, Jon breaks down the five key phases and shares what smart marketers do to reduce friction, build trust, and drive action. He also weighs in on Google’s latest update and what it means for your landing pages—especially if you're still sending ad traffic to a generic site.

If you're not tailoring your funnel to match your buyer’s expectations, this episode is your wake-up call.

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: 

• Jon MacDonald: LinkedIn // The Good // Behind the Click

• Val Riley: LinkedIn 

• Insightly's Website // Unbounce's Website 

Do your customer success managers assist customers? Yes. But do they also handle renewals? Upsells? Expansion? Cross-sell? If it feels like every company writes its own script for this role, you are correct. In this week’s episode of Closing Time, host Geoff Coutts welcomes Kristi Faltorusso, Chief Customer Officer at ClientSuccess, to chat through the evolving role of customer success. Kristi shares her experience in leading customer success teams with a wide range of revenue responsibilities. She talks through the differing skill sets needed and what factors weigh in on the differing structures of CS teams.

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: 

• Kristi Faltorusso: LinkedIn // Client Success 

• Geoff Coutts: LinkedIn 

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

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 burned, this episode is for you.

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: 

• Tim Davidson: LinkedIn // B2B Rizz 

• Val Riley: LinkedIn 

• Insightly's Website // Unbounce's Website 

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.

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 Caruso: LinkedIn // KnowledgeNet.ai 

• Val Riley: LinkedIn 

• Insightly's Website // Unbounce's Website