You’ve got mail!: Email and sequencing best practices and insights

You’ve got mail. It used to be exciting – now, it’s more of a threat. Email is a fundamental tool for every sales team, but the landscape has shifted. Inboxes are crowded and overwhelmed. Paired with longer sales cycles and stricter budgets, more sellers are talking to the vast digital void. 

Call us old-fashioned, but we believe in email. We’ve measured it as a crucial omnichannel ingredient to increasing win rates and it’s what makes sequences possible. But we’re never satisfied with good-enough. We dug into the Outreach platform, and analyzed  millions of sales interactions to better understand the current state of email, and we’re sharing what we found. 

Our exploratory analysis confirms what we’ve seen in other reports: it’s not your imagination, connecting with prospects is becoming more difficult. Luckily, we have the tools and insights to combat this – with or without the Outreach platform.

Open and reply rates are going down

When email software is constantly en garde against unwanted communications, open rates and how they are detected can fluctuate. Even with steady open rates from 2019-2021, it’s worth noting the distinct upward leap in 2022. We’re not under the impression that this 29% increase is because recipients became more enthusiastic to engage, it most likely is a reflection of changing email platform parameters.

But one thing is clear: after years of relative consistency, open rates are declining. When email is the central hub for every LinkedIn reminder, login portal, and third party software notifications – inboxes are getting crowded. And standing out could be more difficult than ever.

Reply all, or maybe not

Open rates can be fickle when you can mark-as-read without ever opening it, so reply rates can be a better indicator of email health. A deliberate response and engagement in the sales cycle gives us a much more accurate picture, but the results are just as discouraging. 

Outreach data indicates a steady YoY decrease in reply rates since 2019, while bounce rates and unsubscribe rates remain relatively consistent. Reply rates have decreased by more than half since 2019 – and this aligns with other sales phenomena we’ve measured. In the Touchpoint Tango, data revealed that sales cycles are 21% longer with win rates 2% lower than in 2020. In our most recent Icebox analysis on cold comms, we discovered the required number of touches across all comms (ice cold, lukewarm, and piping hot) has increased 17% to nearly 5 touches in 2024.

But there’s some good news hidden in plain sight. These relatively even YoY unsubscribe rates demonstrate that outbound efforts have maintained a certain level of quality without becoming more annoying. Meanwhile, these somewhat consistent bounce rates indicate viable deliverability. This suggests that the structure for email comms is somewhat sound, and the true challenge appears to be prospect engagement. 

We hate to say, it’s not you, it’s them. We can also guess that your GTM leaders and boards don’t really want to hear it either. But market conditions cannot be ignored: budgets have remained rigid, workforces are leaners, everyone is still getting the hang of AI, the disconnect is growing between exec expectations and seller reality, and competition is high. These could all be limiting buyer enthusiasm to engage. But not all industries are feeling the same squeeze. 

Industrial complex

Among the industries studied, Education and Finance hold the highest open rates, but each tells their own story. Finance open rates peaked in 2022, and have continued to descend YoY. In contrast, Education open rates reached their lowest point in 2021, and have steadily increased YoY into 2024. 

As we explored in the Icebox, these contradicting industries aren’t immune to market conditions. They could simply be the ones most eager to find a solution.

Show me the money (for now)

This isn’t the first time we’ve noticed Finance’s enthusiasm. Even with a relatively long sales cycle (161 days), the highest number of touches required for cold comms (7 touches), and the highest number of days to a first cold comms response (20 days), Finance still shortened their sales cycles while increasing their win rates YoY – one of the few industries to do so. 

We theorized that a cautious market could have buyers seeking financial resilience, and Financial entities are looking for tools and services to meet this demand. But decreasing open rates and a notable number of required touches for cold comms could be an omen that Finance prospects might be cooling down, and we’ve measured traces of this in their reply rates. Since 2021, Finance reply rates have steadily decreased. These numbers shouldn’t discourage you, but they can inform how you pursue Finance as an industry.

A-B-C, 1-2-2.5% reply rate

Outreach’s most recent cold comms data gave us interesting insight into Education responses. As an industry, Education had one of the fewest number of required touches (5 touches) and fewest days to first response to cold comms (4 days). While Education responsiveness peaked in 2021, only Manufacturing and Education had an increase in reply rate in 2024. With increasing open rates and reply rates, they could be hungry for more solutions and increasing education costs could make more budget available.

Sequence of events – and emails

The only thing better than emails is sequences. Anything that maximizes sellers’ time,makes their jobs easier, and helps them reach their goals more efficiently is music to our ears. At Outreach, we’re passionate about automating and customizing these workflows. We’re also exceptionally passionate about data privacy. We used the real Outreach customer database for this study. As always, to respect customer privacy, data is anonymized, but we do have insight into what kind of sequences tend to be most successful.

Among top performing sequences, we see a lot of Introductions and Contact Us response sequences, but Follow-up sequences make up a majority of the most successful sequences, typically garnering the highest response rates and the most meetings booked. Demo follow-ups, meeting follow-ups, event follow-ups… all make up most of the slots of top performing sequences. 

To better understand successful sequences, we turned our attention to a smaller sample size: Outreach’s President’s Club. And unsurprisingly, personalization seems to be key… again. In the Icebox, we found that, for cold emails, customized email templates have 10% higher open rates compared to regular templates, and more than double reply rates when compared to the standard benchmark.

In our mini President’s Club analysis, P-club sellers tended to lead with personalization in their initial email, then attached to a follow-up sequence. Additionally, degrees of personalization and preference towards automation varied depending on deal size, with big deals receiving more customization.

Better sales emails: tips & tricks

Here comes the fun part: what to do next. This unique email landscape isn’t an inbox death sentence. The game just became more interesting – and you can win. “Emailing has become more challenging but not less effective; it just requires a more strategic approach,” says Outreach Commercial Account Executive Bria Caldwell. 

In addition to our quantitative analysis, we asked Bria and fellow Outreach CAE Steven Monterrey to give us some of their field-tested tips and tricks, with or without the Outreach platform. 

Email tips & tricks

1. Ensure you’re contacting the right targets
   It’s #1 for a reason. Shouting into the void or bad timing makes deal momentum difficult. Lean into your prospecting tools and stay true to your ICP. Conduct thorough account planning and research to determine when and how to approach your contact. If you’re not an Outreach user, utilize our Sales Prospecting Guide and our Email Prospecting Guide for more tips, examples, templates, and more.

2. Use tantalizing subject lines
   Outreach AE Amanda Lockwood said it best in the Icebox: “Have fun with the subject lines!” recommends Amanda. “I sometimes add their first name, or keep the subject all lower case to look more like a conversation. I also love using phrases like ‘From convos with (name of person)’, or ‘Upcoming renewal’ when we know we're going up against a competitor, or ‘From your (prior company) days’ if the prospect used your solution previously at a past company.” Stay appropriately formal, but keep it friendly.
   
   For more subject line help without the Outreach platform, check out our Outreach-approved subject lines.

3. Keep body copy meaningful, brief, and personalized
   “Ensure your emails can be read within 30 seconds,” advocates Bria. “Mine are never longer than three lines per email.” Make your emails short and informational with the focus on the target, rather than yourself. “Write relevant emails that address specific pain points, workflows, or needs of the target persona. Use persona-specific language and tailor your messages.” Steven echoes this sentiment: “I opt for highly personalized messages focused on brevity and personality. My tip: Ditch the jargon and let your genuine voice come through.” And he’s right! Customized emails have 10% higher open rates compared to regular templates, and more than double reply rates when compared to the standard benchmark.
   Outreach’s Smart Email Assist uses AI to streamline email communication by drafting AI-based emails. That way, you don’t need to start from scratch on initial sales engagement emails, email replies, or meeting follow-ups.
   
   If you’re not an Outreach user, we have templates to help you establish yourself, your offering, and next steps, along with objection handling tips. 
4. Be patient & consistent – and respond quickly
   “Be patient and consistent in your outreach,” says Bria. “Regularly engage with prospects so that when they do need a solution, they are already familiar with your value proposition.” According to Outreach data, it typically requires a nearly 5 touches to receive a response from anyone (7 if they’re a cold contact), and your patience and diligence will help secure a response.
   
   As you pursue prospects and follow-up on leads, once you do get a response, don’t lose momentum. Amongst our President’s Club members, their average response time was 90 minutes.
   
5. Go beyond the inbox
   We’re email lovers and they are deeply necessary, but we also recognize that they aren’t a magic bullet. As an organization, we recommend a healthy omnichannel, multi-threaded approach. “About one-third of my meetings come from setting up meetings during other meetings, one-third from phone calls, and one-third from emails,” states Bria.

Utilize an assortment of communication techniques to keep targets engaged and move deals along. Meanwhile, don’t be afraid to build rapport across an organization with multiple contacts. Outreach data indicates when more than one contact is engaged, deals are 37% more likely to close. But cross-department threading has the potential to increase win rates by 56%.

This multi-channel, multi-contact approach brings us to sequences.

Sequencing tips & tricks

1. Maintain variety
   Just as we recommend an omnichannel approach with organic communication, a multichannel approach should be included in your sequences as well. “Use various lines of communication such as LinkedIn, phone calls, and emails to reach out to prospects,” recommends Bria. Incorporate marketing materials and case studies to make every step meaningful and informative.
   

1. Long live the follow-up sequence
   The Follow Up Sequence is undefeated,” says Steven. “Given the majority of my communication is with customers with whom I work with regularly, the follow up sequence gives me more flexibility while ensuring I have consistent touchpoints and  increasing the odds that I get a response or meeting booked.”
   
   When follow-up sequences reign supreme, use them to your advantage. Steven recommends follow-up sequences for:
   • Account Intros
   • QBRs
   • Event Invitations
   • Product Updates
   • Expansion/Cross Sell Opportunities
   • Support Ticket Follow Up
   • Multi threading/Exec Intros
     
   
   “The best thing about the follow-up sequence is that I can use it directly from my Gmail,” states Steven, “meaning less clicks, less screens, and more time to focus on things like account planning, research, and customer meetings.”
   
   
2. Personalize (yes, again)It’s so important, we’re recommending it twice. Spray-and-pray is not a recommended Outreach technique: “Avoid generalizing and blasting emails,” says Bria. “Instead, create sequences tailored to specific personas and their needs. This approach is more effective and personalized.” 
   Outreach President’s Club members tend to lead with personalization, then employ sequences.

Email remains a cornerstone of sales success, but the landscape has changed – and you can navigate this. Winning now requires strategic targeting, creative subject lines, meaningful brevity, and a commitment to multichannel, multi-threaded communication. Whether you're utilizing Outreach or employing these best practices manually, one thing is certain: smarter, more human-centric outreach will always stand out.

Let this be your rallying cry: email is not dead; it's just waiting for you to lead it to new heights.