Cold Email Outreach with Jeremy & Jack

About this episode (#407): In this episode, Jack and Jeremy break down a bold connection request on LinkedIn that skips the usual small talk and goes straight for the pitch. They debate whether this “go for the kill” approach ever works in cold outreach, and if so, under what conditions. Along the way, they define a framework for when pitching in a connection request might actually make sense and when it’s still a terrible idea. Key topics discussed in this episode: Jack and Jeremy unpack what it takes to earn a “yes” at first touch and how to craft messages people actually want to reply to. 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

About this episode (#406): In this episode, Jack and Jeremy revisit the question: should AI be trusted to write and send first-line personalization in cold outreach? It’s late Q2 2025, and AI tools are smarter than ever. But are they smart enough to handle something as nuanced (and reputation-sensitive) as email intros without human review? The guys go deep on how far the tech has come, what’s still risky, and where it might actually make sense in your workflow. Key topics discussed in this episode: This episode is a no-fluff look at what AI can and can’t do for outbound personalization in 2025. Jack and Jeremy break down the tradeoffs, the risks, and where smart filters and prompts can actually help without wrecking your reply rates. 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

About this episode (#405): In this episode, Jack and Jeremy run a two-part teardown of real cold outreach messages. They start by analyzing a LinkedIn message that pitches AI agents for lead generation, then break down a clever follow-up email from a SaaS tool the recipient had signed up for months earlier. You’ll hear what worked, what didn’t, and how to write outreach that actually gets replies, whether your audience is ice cold or just cooling off. Key topics discussed in this episode: This episode is a masterclass in cold outreach psychology, whether your leads are brand new or just haven’t heard from you in a while. 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

📫 Don't miss the best cold outreach tips, join the newsletter - https://quickmail.com/newsletter About this episode (#404): In this episode, Jeremy and Jack dive into a smarter way to structure follow-up emails in cold outreach. Instead of repeating the same call-to-action (CTA) or simply lowering commitment levels, they introduce a sales-letter-inspired approach using upsells and downsells to increase engagement and conversions over time. Key Topics Discussed: This episode is a goldmine for anyone running outbound campaigns and tired of stale follow-ups. Rethink your offers, make your asks more strategic, and turn “no response” into lasting brand engagement. 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 from QuickMail and Jack from SalesBread tackle a tough question from a head of growth at a small B2B SaaS company: How do you succeed in cold outreach when your product lacks a clear edge in a crowded market? The two dive into real-world tactics and mindset shifts that can help founders and marketers compete against bigger players even without a flashy differentiator. Key Topics Discussed: Whether you're selling "salt" or software, you don’t need to reinvent the wheel to succeed. With smart positioning, pricing, and outreach strategy, even undifferentiated products can win. This episode is packed with actionable gems for any B2B founder trying to get traction in a tough market. 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 rapid-fire episode, Jack and Jeremy tackle six cold email and outreach questions submitted by listener Trey. From proper greetings and cultural nuances to incentives and defining success, the hosts share actionable insights based on real-world experience. Whether you're new to outreach or refining your strategy, this episode has something for every B2B emailer. Key topics discussed: - Why using “Hello” in cold email greetings can sound too formal or robotic - The importance of matching your tone to your recipient’s culture or geographic location - Using industry-specific language to better connect with your prospects (e.g., “What are y’all building?”) - Clarifying the definition of a “qualified lead” versus a “prospect” - Measuring the success of cold email campaigns based on conversations started, not just closed sales - Offering gift cards or incentives in exchange for sales calls — when it works and when it doesn’t - The psychology of value perception when offering monetary incentives This episode is packed with practical advice, real examples, and a few laughs as Jack and Jeremy explore what really works in cold outreach. Big thanks to Trey for the thoughtful questions — keep them coming! 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 break down an especially long and highly personalized cold email that made its way through the noise—though not without some controversy. They explore what worked, what went too far, and how AI-driven outreach can either charm or alarm your prospects. Key topics discussed: - The use of deeply personal references in cold emails—and where it crosses the line. - Why referencing hobbies, spouses, and old clients might not earn you points. - The difference between relevance and overpersonalization in outreach. - How AI-generated emails reveal themselves with subtle formatting cues. - Alternative, clearer messaging strategies that could've made the same email more effective. - The importance of a focused CTA and the power of a “trial as a gift” offer. - Predictions for the future of first-line personalization and AI’s evolving role in cold outreach. Less is often more when it comes to personalization. A simple, relevant message that's respectful of boundaries often beats a complex AI-generated pitch loaded with unnecessary personal trivia. 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 break down a simple, no-fluff cold email strategy to help you land your first sales meetings—even if you’re starting from scratch. No marketing budget, no followers, no fancy tools—just a clear step-by-step process to get conversations started with your ideal customers. Key Notes: If you’ve been hesitant to start cold outreach, this episode will show you that it's not only doable—it can be fun and effective. Tune in to learn the baby steps that lead to big wins in sales. 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 brutal reality of the one-second test that every cold email must pass. They explore the psychological and structural cues that influence whether a prospect replies—or hits delete almost instantly. Key Notes: Whether you're running outbound campaigns or fine-tuning your cold outreach game, this episode offers practical, nuanced tips to help your emails survive the one-second test and stand out in crowded inboxes. 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 & Jack reveals a powerful yet under-the-radar LinkedIn feature that transforms how sales professionals can target their outreach. They explore the possibilities and practical applications of this new discovery, comparing it to the psychographic targeting capabilities of early Facebook Ads. Key Notes: This episode is a must-listen for sales pros and marketers eager to build smarter, more relevant outreach campaigns. Tune in and try out the filter yourself—you might just rethink your entire prospecting strategy. 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 return from a break with a fresh teardown of a LinkedIn InMail pitch. They dive into whether the message hits the mark, who it’s really for, and how to make outreach campaigns more effective. It’s a fun, punchy critique packed with real-world advice for sales pros and copywriters alike. Key Notes: This teardown highlights how even simple offers require thoughtful positioning. Jack and Jeremy show that with the right tweaks, even a lukewarm pitch can be reworked into a compelling outreach message 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 unique direct mail marketing piece targeting vehicle owners. We analyze its effectiveness, discuss how similar approaches could work in other industries like business brokerage, and break down the nuances of personalization, format, and copywriting. If you're interested in cold outreach or direct response marketing, this one's for you! Key Notes: A breakdown of a direct mail piece designed to buy used cars The impact of handwritten-style marketing and personalization How this approach could translate to business brokerage and other industries Strengths and weaknesses of the copy, including the use of urgency and credibility The role of objection handling in direct mail vs. email outreach The effectiveness of PS statements and how they can be improved The key takeaway: Less is often more when it comes to direct response copywriting This teardown revealed some important lessons in cold outreach and direct mail effectiveness. Removing unnecessary elements and focusing on clarity can make a huge difference. Tune in next time for more marketing breakdowns! 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 & 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: 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: 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 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 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 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 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: 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/