#394 - 13 Sales Questions You Should Be Asking in 2025

In this episode, Jeremy & Jack break down and analyze two cold email campaigns, offering insights and feedback on what works and what falls short in email outreach. They dive into the importance of personalization, the power of a strong call to action, and common pitfalls in email marketing strategies. Key Notes:  - The importance of a compelling subject line and the impact of personalization. - How using "fishing for no" tactics in your call to action can be an effective strategy. - The role of a concrete case study or specific examples in increasing credibility. - Why emails that sound too generic or automated often fail to engage recipients. - The challenges of offering free services (like a 40-hour trial) and how to make such offers more appealing. - The negative impact of using a generic "from" email address in outreach campaigns. - How tailoring your email to the specific recipient and their business can make a huge difference in outreach success. The hosts wrap up by stressing the importance of authenticity and personalization in cold emails. By refining subject lines, call to actions, and the overall tone, email outreach can be more effective and less likely to fall into the spam folder. About the hosts: Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com

In this episode, we dive into a rapid-fire Q&A on cold outreach strategies, covering everything from leveraging AI for personalization to optimizing LinkedIn profiles for better response rates. The discussion explores how sales professionals can balance automation and human connection while improving deliverability, personalization, and follow-up strategies.   Key Notes: How AI can enhance outreach efforts without losing the human touch Key differences between cold emailing and LinkedIn outreach in 2025 Optimizing LinkedIn profiles to support sales efforts and increase engagement Social selling techniques to warm up prospects before reaching out Strategies to avoid spam filters and improve email deliverability Personalizing cold emails effectively without crossing privacy boundaries The importance of balancing value and promotion in cold outreach With practical insights and actionable strategies, this episode provides a roadmap for sales teams looking to refine their cold outreach approach. Tune in to learn how to stay ahead in 2025’s evolving sales landscape.   About the hosts: Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com

In this episode, we dive into effective sales outreach strategies, particularly when working with a limited number of new prospects. The discussion focuses on prioritizing leads, leveraging high-touch channels, and using engagement signals to maximize impact.   Key Notes: Why "response lists" are more effective than demographic-based lists for prospecting The power of high-touch outreach methods like phone calls, personalized videos, and in-person visits How to identify engaged prospects based on email opens and LinkedIn profile views The importance of making outreach feel personal and avoiding overly scripted messaging Creative approaches to stand out in a crowded sales landscape The evolving trends in cold outreach and why traditional mass-email tactics are losing effectiveness Best practices for balancing personalization and scalability in sales strategies By focusing on genuine engagement and strategic targeting, sales professionals can improve their outreach efforts and build stronger connections with prospects. Tune in to discover actionable tips for refining your sales approach.   About the hosts: Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com/

In this episode, we conduct a deep dive into an SEO-focused cold email sequence, breaking down its structure, effectiveness, and areas for improvement. From subject lines to follow-ups, we analyze what works, what falls flat, and how strategic personalization could make all the difference. If you're looking to refine your outreach strategy, this teardown is packed with valuable insights. Key Notes Initial impressions of the subject line and its ability to spark curiosity. The effectiveness of using organic traffic signals as a lead-in. The value of visual elements like Ahrefs or SEMrush screenshots in email outreach. How messaging can shift to focus on the recipient rather than the sender. Analyzing the follow-up sequence and why it ultimately failed to build trust. The importance of specificity when discussing SEO opportunities. Alternative approaches that could have improved engagement and conversions. Cold email success relies on more than just persistence; it requires value-packed insights and genuine personalization. This teardown highlights the critical elements that can make or break an outreach campaign. Tune in to learn how to craft more compelling, effective messages! About the hosts Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com

In this episode, Jeremy and Jack discuss the evolving landscape of email deliverability and why it's no longer a major concern for most sales teams. They explore how a shift in focus is needed toward refining your list and message rather than obsessing over deliverability, as the technology has already solved many of those issues. Key Notes Why deliverability is no longer a major issue in 2025 due to advancements in AI and automated inbox switching. The importance of having a quality message and a laser-focused list over relying on volume. Real-life examples comparing high-volume campaigns to low-volume, high-targeted campaigns, demonstrating the effectiveness of focused outreach. The shift from optimizing deliverability to improving your outreach strategy, emphasizing smaller, well-targeted lists. The role of AI in list cleaning, ensuring the right companies and people are being contacted. Message optimization strategies, including using social proof and adjusting the ask to increase engagement. Personalization debates—whether AI-based personalization improves response rates or if it’s better to keep things simple and direct. Jeremy and Jack wrap up by encouraging sales teams to prioritize understanding their market, focusing on the quality of their leads, and creating targeted outreach strategies. They remind listeners that deliverability is no longer a bottleneck—it's all about refining the message and the list About the hosts Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com/

In this episode, Jeremy and Jack explore how traditional sales methods can be adapted to today’s business world. They dive into strategies that can enhance your outreach, from in-person interactions to innovative downsells and refining your pitch. Key Notes How Lunch and Learn sessions can be a fresh take on traditional sales tactics. Using alternative outreach methods like sending thoughtful gifts or offering value upfront when cold emailing falls short. The power of in-person connection—visiting potential clients or attending events to build relationships before pitching. Networking with competitors by becoming a customer of theirs or engaging in their communities to learn more about their audience. The benefits of downselling as a way to maintain engagement and create opportunities for future business. The need to adapt your pitch when the current approach isn’t working, with a focus on creativity and relevance. Why investing more in your outreach efforts can lead to better long-term returns, even if it requires more upfront costs. Jeremy and Jack wrap up by highlighting the importance of experimenting with different strategies and staying flexible with your sales techniques to meet your target audience’s needs. About the hosts Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com/

In this episode, Jeremy and Jack dive into the evolving world of sales outreach, discussing how the traditional approach of cold emailing and templates may be shifting toward more organic, conversational strategies. They explore the concept of using a two-part campaign to warm up prospects and how starting with a casual conversation can lead to meaningful business interactions.   Key Points: The concept of a two-part sales campaign A real-life example of a company using a "messenger" to start casual conversations before transitioning to sales. The importance of warming up prospects before pitching, as opposed to direct sales messaging. How AI and tools may influence outreach strategies in 2025, focusing on more natural, less templated interactions. The future of outreach: Moving away from volume-driven strategies and toward more personalized, slower-paced campaigns. The psychology of outreach and the idea of “pivoting” from a casual to a business conversation on different channels. The potential death of traditional sales templates as personalization and conversational marketing take center stage. The episode wraps up with predictions for the future of outreach, suggesting that in the near future, personalized, organic conversations will play a larger role in sales strategies. The death of the template and the rise of AI-powered outreach are expected to reshape the industry. About the hosts: Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com/

In this episode, Jeremy and Jack dive into the details of a multichannel lead generation campaign they've been working on for 2025. They walk through the campaign's strategy, including LinkedIn and email outreach, while sharing valuable insights on optimizing connection requests and cold outreach.   Key Points: Combining LinkedIn and email strategies to reach lead gen agency owners.  Tips on writing connection requests and balancing transparency with personalization.  Crafting messages with a value proposition and focusing on superior deliverability. The power of embedding images to showcase analytics and improve engagement. Transitioning from simple questions to more impactful, value-driven CTAs. The benefits of changing communication platforms, like from email to LinkedIn, for better engagement. The importance of adding more personalized touches when leads show interest. Jeremy and Jack wrap up by reflecting on the effectiveness of their strategies and how the use of visuals and personalization can elevate lead generation campaigns. Tune in for more insights in upcoming episodes as they continue refining their approach for the new year.   About the hosts:  Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com/  

In this episode, Jack and Jeremy dive into the art of prospecting for outbound sales - exploring strategies that prioritize efficiency and results. The hosts break down a unique visualization of the prospecting process to help sales professionals refine their approach.   Key Points Understanding prospect proximity to your offer Introducing a unique visualization to represent prospect engagement Trust, decision-making power, and belief in your solution as key factors Leveraging past customers and referrals Marketing tactics to boost engagement while reducing barriers to entry This episode provides actionable insights into visualizing and optimizing your prospecting strategy. Whether you're a seasoned pro or new to outbound sales, you'll find tips to help you close more deals and engage more effectively with your prospects.   About the hosts: Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com

This episode discusses strategies for conducting cold outreach during the holiday season, such as the best days to send emails, whether to pause campaigns during holidays, and opportunities to connect with prospects in a more personal way. Key topics discussed: Data on email performance based on send days The pros and cons of maintaining cold outreach campaigns during holidays like Thanksgiving and Christmas Differences in email performance over the holidays based on industry Ideas for more personal outreach during the holidays Jack and Jeremy encourage listeners to think creatively about how they can reconnect with customers and prospects during the end-of-year holiday period, whether through email, phone, physical mail, or other personalized outreach. They wish all of their listeners successful outreach and a happy holiday season.   About the hosts: Jack Reamer founded SalesBread.com – the lead generation agency that brings B2B companies 1 lead per day by sending ultra-personalized LinkedIn messages and cold emails. Show listeners can book a free, 15-minute lead generation brainstorm session here: https://salesbread.com/contact/ Jeremy Chatelaine founded QuickMail.com – the most performant cold email platform to get replies, thanks to industry-leading features such as Deliverability AI and Advanced Stats. Start your trial today here: https://quickmail.com