The Icebox: The inside scoop on cold calling and emailing

You had me at hello… if only it were that easy. Cold calls and emails are an unwavering sales tradition. Lead tracking and qualifying tools (Outreach included) are getting better all the time. But cold comms remain constant, because even with a heightened challenge and conflicting win rates, they still work – but only if you have the right tools and technique.

Outreach was made to support the entirety of the sales cycle, especially cold comms (our name is literally Outreach). So we took a look under the hood to see what’s really going on in the icy state of cold comms. The Outreach Sales Execution Platform serves millions of sales and revenue interactions worldwide, so we utilized our internal database of global, anonymized selling data for exclusive insights to boost your cold calls and emails.

And the spirit of cold comms, we’re getting straight to the point. Stay cool.

Do you have a minute? Or a few more…

In general, sales cycles are getting longer and win rates are getting lower, and the number of required touches reflects that prolonged sales cycle.

Before digging into the nitty gritty of cold comms, we wanted to establish a baseline for the general state of first communications. This data sample includes touches required for all first interactions – ice cold, lukewarm, and piping hot. And the required number of touches has been on a steady increase since 2021, increasing 17% to 4.81 touches required in 2024.

As discussed in Outreach’s Touchpoint Tango, sales cycles are 21% longer with win rates 2% lower than in 2020. It appears that prospects are feeling more hesitant to engage and more hesitant to progress.

An unexpected position

Willingness to engage is flexible, at least according to position. If you’re chasing a Finance VP, expect to make at least 17 touches before they engage, they’ve only become more inaccessible YoY. But if you’re trying to catch the eye of a Finance Executive, it may only take a little more than 6. This power asset may increase openness, but they’re not the only department with varying dynamics.

Sr. IT and IT individual contributors, Finance Execs and Directors, and Marketing Directors all experienced a YoY decrease in required number of touches from 2023 to 2024. Meanwhile, IT VPs, Finance VPs, HR Directors, and Jr. Sales all experienced the largest YoY increases. But why? Since there aren’t any clear lines of connection between these roles, it’s hard to make any sweeping generalizations… but it sure is handy to know what to expect when you’re trying to hit quota. 

This is real, live data taken directly from the Outreach platform. Outreach users, rather than the internal Outreach data team, assign (or don’t assign) these title personas. Our Other categories tend to be the broadest, and we expect that they contain a hearty mix of ranging titles, including above and below the line. But the title-specific categories may be the most valuable, as it suggests those who are maintaining diligent records and using Outreach comprehensively are more likely to be diligent in their communication efforts. Their dedication to detailed use of Outreach could provide a clearer picture of what to expect if you’re using all of your resources and pounding the pavement.

What surprised us next wasn’t the detriment of cold comms, it’s how they didn’t differ too drastically.

Brrr… it’s cold in here, yet comfortable?

… at least for cold emails and calls. Cold communications are naturally daunting, talking to strangers and all. But our data indicates that igniting cold comms don’t generally take drastically longer than our sample of general first communications. 

It may take nearly 5 touches to get in touch with any given contact, but amongst this sample of first-touch, outbound, non-qualified leads across Outreach users demonstrates that it takes an average of just 7 touches to engage in cold comms – but depending on your prospect’s department and industry, it could be as few as 3.

This cold comm resilience can likely be attributed to what we love about cold comms in general: sellers are capturing potentially missed opportunities at a time when prospects need solutions. 

Internal restrictions and market conditions 

This subtle delay in required touches for cold comms could be explained by our latest sales cycle data. In the Tango we speculated that the market has shifted away from growth-at-any-cost and towards a profitable growth mentality, where larger buying committees and stricter budgets have prolonged negotiations, resulting in longer sales cycles and decreasing win rates. But this enthusiasm to engage suggests that while internal circumstances may disrupt inbound inquiries, the problems unique products solve still remain – and individual contributors want the solutions, making them more willing to interact with outbound, even if they are combating internal resistance.

In 2023, everyone settled into this new standard, trying to make due with what they already had available (advice Outreach supports). Sales requires resilience and internal restrictions do not eradicate market conditions. In 2024, a couple more touches could be just enough to break through organic, ongoing issues and kick start a sales cycle. The official and unofficial restrictions placed on new purchases and expansions does not alleviate the real problems leaders and individual contributors need solutions for – and a little more encouragement could introduce them to your sales cycle. 

When we compare sales cycles initiated with cold comms versus the whole of our database, cold comms sales cycles were roughly on par with the general sales cycles – at least in the Outreach platform.

Executive decisions, made sooner

We highlighted that individual contributors and leaders are responsive to cold comms because the real data surprised us. As expected, the higher up the corporate ladder, the longer you’ll typically have to wait for a prospect’s first response to cold comms, but you may be able to do so in fewer touches.

Amongst our cold comm data, we measured a similar twist we saw in our general population of first communications: executives seem to be more accessible than anticipated. Directors tend to respond in fewer days, but depending on the department, you may access an exec with fewer touches on a longer timeline. According to our cold comms data, it may take 18 days to receive a response from a legal exec, but it may only take 5 touches. Meanwhile, in just 13 days, you could receive a response from a legal director, but it will likely require 6 touches. 

Customer Success has the quickest response time with the fewest number of touches, with Directors responding in just 4 days and 3 touches. This could be a result of the conditions discussed earlier, where many organizations are being told to make due with the tools they already have. The providers that create favorable customer experiences could be feeling the squeeze and eagerly looking for solutions and support.

Department of Variety

Executives may be surprisingly accessible, but industry could really prolong a first response to cold comms. Financial Services has the longest timeline to a first response, requiring 7 touches and 20 days. This aligns with Outreach’s general sales cycle data, where finance had the longest sales cycle amongst measured industries at 161 days. Conversely, Security Software boasted the shortest timeline to response and the fewest required touches: 3 days and 3 touches.

Personalize to familiarize

Inboxes are crowded, and how you approach your prospects could make a difference. Personalization is key to catching their eye and spurring engagement on cold emails. 

We’ve tracked a steady YoY decrease in cold comm open rates YoY since 2022, but customized email templates have consistently maintained the highest open rates when compared to both benchmark and standard templates. Customized email templates have 10% higher open rates compared to regular templates. Twenty twenty four cold email open rates are trending downward, making personalization more important than ever.

We measured the most dramatic benefit of personalization in increasing reply rates, sparking the sales cycle. Customized email templates more than double reply rates when compared to standard benchmark. In cold comms, spray and pray can be tempting, but accurately recognizing, resonating with, and identifying your prospects’ unique needs and circumstances can inspire communication.

What to do right. now. to heat up cold calling and emailing

Data insights are crucial, but selling is also a deeply human act. We wanted to give you real action items to take with you that encompass the best of both worlds: Outreach’s exclusive proprietary data and a few field-tested tips and tricks from Outreach cold comm royalty.

Outreach's data-backed tips & tricks

Hunker down

Even if you’re not an Outreach user, Outreach timelines can help you better anticipate your deal timelines. If you know you’ll need at least 5 touches for any first touch communications and at least 7 touches for cold communications, you can prepare and maintain optimism. Remember that these are averages, so expect fluctuations and prepare accordingly.

Dig in, aim high

Don’t shy away from your target decision makers. Depending on department and industry, capturing the attention of top leaders may be easier than those at the director level. Targeting leaders also increases your likelihood of executive alignment and easing any fears or uncertainty, pushing towards closed-won.

Variety is the spice of cold comms

Include a medley of communication channels to engage your target and progress your deals. In a recent Outreach omnichannel analysis, incorporating calls can shorten sales cycles and integrating meetings can increase your win rates – but for the highest win rates, meetings and emails are the most powerful combination. VP of Sales Angela Garinger is partial to voicemail, especially with the rise of voicemail transcriptions and Outreach’s voicemail feature.

Speaking of variety, don’t forget to vary your contacts via multithreading. Use those easier-to-access higher ups to your advantage, but you should still create connections with a prospect’s team and growing buying committees. 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%.

Personalization 

Outreach is awesome, but YOU are the secret ingredient. Personalize templates and scripts with custom, human moments to amplify your communications and cut through the noise. Customized emails have 10% higher open rates compared to regular templates, and more than double reply rates when compared to the standard benchmark. 

Use every tool in the box

Obviously, we’re biased towards Outreach as the best tool to manage your deals from cold comm conception to deal execution and customer management. Kaia, our Conversation Intelligence tool, provides real time conversation support and analysis so you can make the most of a first impression (plus it moves deals faster and increases win rates). Smart Email Assist guides email creation for maximum engagement and efficacy. The Pipeline Generation Report calculates your exact required outbound to hit your goals. And Outreach’s deal management and forecasting tools help you better manage your cold comms and plan your quarter… and that’s just what we can fit in this paragraph.

If you don’t have Outreach, leaning into whatever tools you have should help you boost your efforts. Diligently follow deal tracking and review call recordings to better assess and improve your efforts.

You can also utilize Outreach-approved email templates, subject lines, and objection handling to get started. You can also apply the actual formula we use to inform the Pipeline Generation Report, along with our trusty calculator. 

Know when to hold ‘em, and when to fold ‘em

We use 10 as the magic number here at Outreach. After 10+ attempts without response, it's usually time to move on. No target wants to feel pestered. Exit the conversation graciously with a gentle "break-up" email – sometimes it can even spark engagement. Timing is everything in sales. Today's unresponsive prospect could be tomorrow's hot lead.

Amanda’s tips & tricks for cold calling

Meet Amanda Lockwood – she’s a Sr. AE at Outreach and renowned for her cold comm techniques and effectiveness. We asked her for her field-tested insights to make the most of cold emails and calls. Naturally, they’re mostly rooted in the Outreach platform, but even if you’re not an Outreach user, you can adjust these tips to fit your tech stack.

Use your tools and stay prompt

We said it earlier, timing is everything in sales. And if you need 7 touches to get a response, sellers need to be timely. “I rely on Outreach to alert me when a prospect is opening my emails,” says Amanda, “so that I can call them immediately as they're opening the email.” If you don’t have Outreach, turn on read receipts whenever and wherever you can so your communications are always diligent.

Keep it casual and get to the point

Time is money for sellers, and the same rule applies to your targets, so no dilly-dallying. “I always start off my calls, after greeting, by saying ‘The reason for my call is......’ and I keep my call to action casual too. Something like, we can figure out together if it makes sense to loop in others, but thought it could make sense to chat with you because......" Amanda is quick to establish the who, what, when, where, and why while maintaining the humanity of the conversation.

Sensational and conversational! 

You never get a second chance at a first impression, so maintain a pleasant-ness to the conversation but don’t forget that this is the kickstart to a deal. “This is like a mini discovery call,” explains Amanda. “Try and get one pain, or challenge, or broad initiative that you think your solution can apply to. That way, you have some ammo for your follow up and can tailor the initial meeting to that specific need.” This is a great way to ignite the process and maintain momentum throughout the sales cycle.  

Amanda's tips & tricks for cold emailing

Good research = strong follow-up

Plenty of cold contacts circle back around. Part of customizing your templates should include any previous information. “I always jump straight to the Replied section of a prospect’s emails in Outreach. I scan what they've said to us in the past, and if they've ever said to us ‘reach back out in X months’, I come over the top of that email with my reason for reaching back out at that time. I think it helps because the prospect sees an email in their inbox that looks like it was an ongoing thread they've replied to previously vs. an ice cold email.” Very savvy, Amanda, very savvy. 

Fun & creativity produce approachability

You don’t need to know psychology to know that people prefer fun to un-fun. And starting strong with the right subject line allows your customized template to really shine. “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. 

Short, sweet, and to the point

We’re noticing a common theme in Amanda’s techniques: get. to. the. point. Especially when aiming for those refreshingly accessible leaders. “Keep emails short for ATL personas,” advises Amanda. “I outline the reasons for why I'm reaching out and get straight to the point. Cut out any fluff words, fluff adjectives, remove ‘I, me, my’ language where you can, and make it about them! My call to action in emails is typically not ‘Hey wanna meet’ but rather, ‘Is this accurate?’, or ‘Any interest in chatting further?’, or ‘Would it make sense to chat now considering your upcoming renewal?’" Quick, accurate communications keeps the conversation respectful of everyone’s time while also gathering pertinent information and moving the conversation forward.

Welcome to the ice age

Call us quirky, but we love cold comms, mostly because Outreach was built specifically for outbound. Cold comms, and outbound in general, provides the opportunity for authentic connection and uncovering needs that may not be evident through other channels. It offers immediate feedback and the opportunity to refine sales strategies and techniques in real-time, driving both personal and team growth. Not to mention it keeps the higher-ups happy, because they know you’re doing whatever it takes to hit goal.

We live and die by the data, but our love affair with cold comms is a widespread philosophy here at Outreach. VP of Sales Angela Garinger said it in her 2024 Sales Predictions: “Get. On. The. Phones. You should always be on the phones, cold calling will never die.” Our Executive Chairman (and former CEO) Manny Medina said in our Sales 2024 Report reaction video: “Sellers who don't [cold call] have skinny kids… [Don’t] lose this ability to just walk up to somebody you don't know and then check a conversation, find a problem, and perhaps find a solution, which is a quintessential human activity…”

Cold calling and emailing takes courage and resilience. And you only get better the more you practice. The intersection of market conditions and the evolution of sales technology can give you a serious boost, but only if you’re willing to enter the ice age of cold comms. We’re rooting for you. After all, the cold never bothered us anyway, and it shouldn’t frighten you away from your goals either.