Closing Time: quick insights from sales & marketing experts – Details, episodes & analysis

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 

There’s nothing funny about sales…or is EVERYTHING funny about sales? That’s the question for this week’s Closing Time guest, Tom Boston.

The daily trials and tribulations of the modern seller are happening in offices and homes across the world every day. As a former Brand Awareness leader for SalesLoft, Tom created a safe, fun place for salespeople to relate to each other and find camaraderie in a profession that can often feel lonely and full of rejection.

In this episode of Closing Time, Tom shares his journey from SDR to Chief Funny Guy, offering insights into humor in B2B sales and some tips and tricks on standing out with personal branding. We were lucky enough to catch him on the cusp of his next professional venture. Come have a laugh with us!

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: 

• Tom Boston: LinkedIn //  YouTube // Twitter // Instagram // My Sales Coach

• Val Riley: LinkedIn 

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

It’s midway through 2024, and you’re a new sales leader…congratulations! Now you’ve got to get to work. The current and future state of the organization is on your mind.

How can you make an impact right away, keep 2024 goals moving, and still begin to plan for 2025 quotas?

In this episode, Dave welcomes Meg Peterson of On Deck Leadership Consulting to discuss what it’s like to join an organization in this role at this moment in time and how successful sales leaders can navigate it.

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: 

• Meg Peterson: LinkedIn // On Deck Leadership

• Dave Osborne: LinkedIn

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

Your RevOps team is the key to launching and maintaining a high growth trajectory for your business.

In this episode of Closing Time, Dave Osborne is joined by Eddie Reynolds, a RevOps consultant and CEO of Union Square Consulting, to hear about a model Eddie developed while working with high-growth businesses. Dave and Eddie will talk through sales ops, marketing ops, and RevOps. Then, they’ll break down the five aspects of the model and talk about how each step can be accomplished by your team. Watch the episode on YouTube. 

Want to stock your bookshelf on us?

Enter the giveaway to win a $100 Amazon gift card to purchase books authored by Closing Time guests. 

Connect With: 

• Eddie Reynolds: LinkedIn 

• Dave Osborne: LinkedIn

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

The B2B sales compensation market shifts quickly – how are you keeping up in 2023?

In this episode of Closing Time, we’ve invited Amy Volas, strategic advisor and owner of Avenue Talent Partners, to break down what's driving the sales compensation market, risks to be aware of, and the importance of a strong sales hiring process. Why do A-players leave? Find out! 

Want to stock your bookshelf on us?

Enter the giveaway to win a $100 Amazon gift card to purchase books authored by Closing Time guests. 

Connect With: 

• Amy Volas: LinkedIn 

• Dave Osborne: LinkedIn

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

You’ve heard about ChatGPT in the news and online, but how exactly does it benefit Go-to-Market professionals?

In this episode of Closing Time, columnist, author, and host of the Paychex Thrive business podcast Gene Marks joins Insightly’s Chip House on Closing Time to go over five areas where you can start using ChatGPT today to save on resources and time. Actionable tips for salespeople, marketers, and customer success professionals are included. Watch the episode on YouTube. 

Want to stock your bookshelf on us?

Enter the giveaway to win a $100 Amazon gift card to purchase books authored by Closing Time guests. 

Connect With: 

• Gene Marks: LinkedIn

• Chip House: Twitter // LinkedIn

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

Looking to supercharge your outbound sales strategy in 2023? Most sales leaders use LinkedIn Sales Navigator to fuel their outbound sales process. But, as we have learned, very few have mastered it.

In this episode of Closing Time, LinkedIn Ambassador Sam McKenna, does a deep dive into LinkedIn Sales Navigator to showcase how users are underutilizing the tool and highlight features and tips most sales leaders are ignoring. Watch the episode on YouTube. 

Want to stock your bookshelf on us?

Enter the giveaway to win a $100 Amazon gift card to purchase books authored by Closing Time guests. 

Connect With: 

• Sam McKenna: Website // Twitter // LinkedIn

• Val Riley: LinkedIn

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

Are MQLs dead? Marketers have relied on generating Marketing Qualified Leads (MQLs) for years, using them as a critical metric to measure success. But treating all MQLs the same is a mistake. 

John Short, CEO of Compound Growth Media, joins Chip House in this episode of Closing Time to talk about the paid media strategies that drive MQLs. He’ll also talk through how the source of your MQLs results from the level of intent and how bucketing them differently is the key to conversions. 

Watch the episode on YouTube. 

Want to stock your bookshelf on us?

Enter the giveaway to win a $100 Amazon gift card to purchase books authored by Closing Time guests. 

Connect With: 

• John Short: LinkedIn

• Chip House: Twitter // LinkedIn

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

Buyers – especially in B2B – learn about products and services in various ways. As social media platforms like TikTok continue to gain popularity, it becomes increasingly difficult for marketers to track web traffic and social engagement with traditional analytics tools.

Enter the phenomenon of dark social – something that is guaranteed to impact your brand. Author and CEO of Zen Media, Shama Hyder, will break it all down for you in this episode of Closing Time. She's answering the obvious questions: What is dark social? How does it affect companies? How can I leverage it? Watch the episode on YouTube. 

Want to stock your bookshelf on us?

Enter the giveaway to win a $100 Amazon gift card to purchase books authored by Closing Time guests. 

Connect With: 

• Shama Hyder: Instagram // Twitter // LinkedIn

• Chip House: Twitter // LinkedIn

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

Happy Women's History Month! Female salespeople are statistically proven to have better outcomes (e.g. more wins) than their male colleagues, and yet the profession is still male-dominated. 

In this episode of Closing Time, sales leader Charlotte Lloyd dives into this phenomenon, looking at what attracts and repels women from the profession and how women salespeople can find the right businesses to use their talents and succeed. Watch the episode on YouTube. 

Want to stock your bookshelf on us?

Enter the giveaway to win a $100 Amazon gift card to purchase books authored by Closing Time guests. 

Connect With: 

• Charlotte Lloyd: LinkedIn

• Val Riley: LinkedIn

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