Cold Email Outreach with Jeremy & Jack

In this episode, Jeremy and Jack do a deep dive into recent Microsoft email deliverability issues, which have been affecting cold emailers and leading many to struggle with their email campaigns. Microsoft's recent changes to combat spam may have unintended consequences for legitimate senders. Understanding these challenges is vital for successful email outreach. Key Takeaways: What's causing sender bounces Avoiding issues from email volume The importance of unique content New AI applications and automation Best practices moving forward Mastering Microsoft's deliverability requires smart strategy and adaptability. With targeted email practices, AI-driven content, and vigilance, senders can avoid spam filters and drive high engagement for successful campaigns.  About the Hosts: Jack Reamer founded SalesBread.com - the lead generation agency the 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  

Hello outbounders! Today we’re going to reveal how to go from 0 to 1000 LinkedIn connections in a very short period of time.  Say you are looking for influencers in your field to give you life career advice. Here is what you can do to get to a meaningful network of the right people on LinkedIn in 3 steps: Start small  Use low hanging fruits Make your dream connections That’s it! Now go do some LinkedIn connecting and use it to your advantage! Happy cold emailing! Jeremy and Jack

Today we are joined by Lukas Mikelinich, VP of Sales at Saas platform Negotiatus, who just had the best sales month in the company history this May. He is going to talk about how to find your way through Covid time and how to run an effective SDR team. Enjoy!  HERE’S WHAT WE COVER IN THIS EPISODE: How to pivot quickly from pre-Covid to a new climate Re-thinking the biggest value you can offer How to set new instructions for your SDR team What you can achieve with a high level of personalization How to deal with “not interested” answers How to hire top performers for your SDR team How you can assess the coachability level when hiring someone Lucas reminds us to remain agile - there are times when the biggest value you can bring is NOT your core offering; you have to be more creative and think of a better way to serve your clients.  Happy cold emailing! Jeremy and Jack Resources: Never Split the Difference, a book by Chris Voss and Tahl Raz  The Sales Acceleration Formula, a book by Mark Roberge Sign up for our course – Cold Email Outreach Masterclass (https://course.quickmail.io/)

About this episode (#409): In this episode, Jack and Jeremy sit down with sales legend Josh Braun to explore how to start smarter, more effective cold outreach conversations. They break down Josh's "poke the bear" method, a way to uncover hidden pain points without triggering resistance, and share practical tips for making prospects pause, think, and actually want to talk to you. Key topics discussed: Why cold outreach fails when it starts with pitching or convincing How to "poke the bear" by asking questions that expose invisible problems Real-life examples from malls, car washes, and contractor bids that illustrate the method How to use emotional echoing to make people feel truly understood Why it's better to walk away from a bad fit than try to force a sale  How to tailor your message based on job titles and switching risks What Chris Voss taught Josh about silence, trust, and listening for truth The best cold outreach doesn't push, it creates a moment of reflection. Ask the right question, listen well, and let your prospect talk themselves into the next step. 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 (#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: Why most people shouldn't pitch in a connection request The rare exceptions where a direct pitch can work The role of curiosity, pain, and timing in message effectiveness What makes a product demo-worthy based on novelty alone Real-world examples of campaigns that broke the rules and won  The blurred line between "product-market fit" and compelling messaging When list-building and timing matter more than copy itself This teardown shows that even hard rules in cold outreach have exceptions if your offer hits the right nerve. 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: Why letting AI send unchecked intro lines is still a risky move How the quality of personalization has improved and where it still breaks Why buyer awareness of AI is making personalization harder, not easier The evolving role of the first line (and why the PS line might be safer) What makes a smart AI prompt and how to reduce hallucination risk Testing AI-generated personalization vs. handcrafted lines When AI might make sense for high-volume outbound vs. niche campaigns 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: Why vague or generic subject lines instantly signal cold outreach - The dangers of pitching without credibility, proof, or a clear ask How to use curiosity properly in cold messages (and when it backfires) Why offering value or reciprocity makes outreach more effective A teardown of a SaaS follow-up email that used a "you never used your free credits" angle The difference between cold, warm, and "lukewarm" outreach (and why lukewarm might be your best audience) How small, specific asks can increase reply rates 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:  Why sending the same CTA in follow-ups is a missed opportunity Introducing a follow-up "ladder" with escalating and descending offers The psychology behind "foot in the door" vs. "door in the face" techniques Using varied offers (video, guest post, webinar, trial) to maintain attention and add value Why the third ask might get a "yes" even if the first two didn't How to keep leads in your universe (e.g. newsletter, YouTube) even if they're not ready to buy The importance of investing thought into offers, not just copy, during outreach planning 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: The importance of market education and timing when entering a saturated niche Competing on price: the most basic but often effective strategy for early traction Why strong marketing can outperform a superior product Alternative ways to position your offer—such as "trial as a gift" Why commoditized tools (like email verification) need creative outreach angles Using consulting or audits as a Trojan Horse to sell your core software The game-changing idea of targeting consultants and incentivizing them with affiliate deals 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:  How to define your Ideal Customer Profile (ICP) without overthinking it Why starting with just 20–30 hand-picked prospects is more effective than buying a list The exact cold email script you can send to "dead leads" to re-engage them Tips for writing personalized, human emails without using any automation How to craft a value-driven follow-up that surprises and engages your prospect Why simple yes/no call-to-actions outperform vague "let me know" language When and how to scale up your outreach once the manual process starts working 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:  Why you only have 100 milliseconds to make a first impression The importance of email layout, subject line, and paragraph length How visual and sender identity cues (like avatar and display name) can make or break your outreach The red flags of impersonal or poorly set-up automations (e.g., email addresses instead of names) Why the first sentence must immediately answer "Is this for me?" The value of smart, skimmable call-to-actions and how placement affects response rates Why unsubscribe links, oversized signatures, and fake flattery can kill trust—and how to fix them 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:  The discovery of LinkedIn's "followers of creator" filter and how it mirrors Facebook-style psychographics How to find U.S.-based CEOs who follow specific influencers like Alex Hormozi Exporting search results to build targeted outreach lists The potential of combining creator-following filters to identify shared beliefs or preferences in prospects Real-world applications, including event marketing and webinar promotions Comparison between Sales Navigator and basic LinkedIn search features The broader implications for the future of LinkedIn's ad and outreach capabilities 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: The importance of clear value propositions in outreach messages Why lazy list-building kills good campaigns How to rewrite messages to include relevant personalization and social proof The role of silent objections and when to handle them in cold emails Whether certain low-ticket offers really warrant a call-to-action for meetings Tips for list targeting: looking for buyer signals like team size and premium usage The case for directing recipients to a high-trust landing page vs. asking for a call 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: 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