The Art of Cold Outreach

Ding. Better check my email, it’s probably my boss.

Ping. Shut the front door: An influencer just tagged me!

Ring. Someone’s actually calling my cell? It must be an emergency.

As a sales rep, your cold email, call, or LinkedIn message may seem like a whisper in a hurricane.

Cutting through the noise of everyday life takes innovation and care. Earning someone’s attention requires personalization and relevancy. Landing a meeting demands grit and perseverance.

Cold outreach is a tough challenge.

In times of economic uncertainty, it’s even tougher. Especially for sales reps who’ve only experienced boom times.

How can you land a sales meeting when companies are tightening budgets and headcount, and your ideal prospects have no time to spare?

Today reps aren’t just fighting for attention in prospects’ inboxes; they’re battling for priceless real estate on prospects’ calendars.

Cold outreach is still necessary, and success is still possible.

“If you have the ability to help someone, you owe it to them to reach out to them,” says Mark Hunter (aka The Sales Hunter). “Sales is about helping others see and achieve what they didn’t think was possible. How are they going to know you can help them unless you call them?”

How do sales and marketing teams feel about these challenges?

We surveyed the attendees of Growth Week 2023 to learn how they’re tackling challenges, and which tactics they plan to use to remain competitive. Here's what they had to say:

The best sales reps tackle the challenge with a fearless mindset. They’ve honed innovative strategies and tactics. They’ve learned how to be heard above the roar. How are these successful sales reps getting replies, landing meetings, and generating revenue?

In this guide, we’ll:

• Reveal proven prospecting strategies for uncertain times

• Share cold-outreach insights from successful sales pros at companies like Gong, Sendoso, and Calendly

• Help you grab attention in a saturated digital environment

• Break down proven, cold-outreach frameworks and cadences for an omnichannel approach

• Embrace sales technology for better outcomes, including using AI wisely

You'll get the tools to snag the attention of the right people at the right time. Even better, our pro tips will help you keep prospects’ attention long enough to land the sale.

It gets a bad rap, but it still works if you work it.

Reaching out to someone who has zero connection to your business can seem intimidating. Expect to be ignored and get hung up on. Persist. Be resilient. Going in cold does open doors and lead to conversions. When approached strategically, cold outreach reaches a larger, more targeted audience than just waiting for leads to fall from the inbound marketing sky.

Jason Bay, Founder and CEO of Outbound Squad, told Calendly there’s a misconception about top-performing sales reps.

“I think people are always expecting like, oh, they make the most amount of calls or they send the most amount of emails,” Bay says. “The thing that I’ve found over my years of being in business development, the most successful sales reps are the ones who do research and outreach most consistently.

“They don’t have these huge spikes in mass outreach, because they’ve always got enough conversations going to get some meetings booked.”

“When I first started cold outreach, I was awful. People were hanging up on me. Emails were bouncing. It was a terrible experience,” says Morgan J. Ingram, Founder and CEO of AMP. “However, once I began to commit to my craft, it led to small wins. Those small wins began to snowball, leading to me doing a cold video to an opportunity that led to my biggest deal.

“We all start bad when we start something new, but we can accomplish a ton if we focus on improving.”

Percentage of sales personnel who give up after a number of rejections

Source: Velocify

Almost half (48%) of salespeople don’t make a follow up call, yet according to Velocify, 93% of converted leads are often reached only by the sixth cold call attempt.

Common mistakes in cold outreach

Avoid pitches

A tiny fraction of any market is actively looking to change providers at any one time. That means for every 100 people you call, only a small handful want to hear your pitch.

And yet, sales reps love to pitch.

As soon as a prospect answers your call, admit it: You’re tempted to launch into a seller-centric sales pitch, listing out features, functions, awards, and accolades.

The reality: Buyers don’t care about your pitch. What matters to them are their challenges, their goals, and their company.

"We don’t close a sale. We open a relationship.”

“Today’s prospects expect more,” Cottle says. “You have to make sure that your value pitch — or the way that you’re engaging prospects — is relevant to them and not just relevant to the product that you’re trying to sell.”

Early on, ask prospects questions like:

• What challenges are you facing?

• What are your productivity pain points?

• Do you have any big initiatives this year?

• Are you pursuing any new strategic objectives or industries?

In practice that might sound like:

“In working with our [insert industry] clients, we’re hearing a lot about how difficult it is to adapt to [insert industry challenge] right now. Is that something you’re struggling with, too? If so, here’s how we’re helping a few other companies like yours improve outcomes. [insert ROI examples and/or case studies] Are you interested in chatting further?”

Be so well versed, you don’t sound scripted

Technology plays a significant role in modern sales. Using tools like CRMs, automation, and AI to streamline processes, gather insights, and personalize communication is necessary. But it should never overshadow the human element, says Sendoso’s Katie Penner, Head of Sender Relations. Balance efficiency with authentic, human connections to create a seamless and memorable experience for your prospects, clients, and customers.

“I hear from buyers every day that they are experiencing buyer fatigue — and in fact, I’ve felt it myself,” Penner says. “Buyers are constantly bombarded with hundreds of emails, tons of calls, countless DMs, all while being in back-to-back meetings daily. As a buyer, I can tell you that a lot of these messages are automated and today, we are dealing with ChatGPT generated messages that feel very generic and unauthentic.”

When creating new messaging, Ingram at AMP recommends running it past the internal experts at your own company. Targeting a recruiting ICP? Ask a recruiter at your company to review your ideas and give you feedback. Most likely, their objections are the same ones you’ll encounter with prospects.

Prepare for objections

Objections are not the end of the conversation.

In fact, almost any objection is an opportunity to deepen the conversation and learn more about your prospect. The best-performing reps plan, prep, and rehearse for the most common roadblocks. Sellers who learn how to successfully defend their product and overcome objections can have close rates as high as 64%.

But objection handling is tricky to do on the fly.

Although objections come in many different flavors, they boil down to four common archetypes:

If someone is already paying your competitor, that’s a great sign. They’ve already bought into your value prop and have the budget to invest in a tool.

Ask what they love about their current solution, and any features or customer support areas that are missing. Have your battlecard ready to go and bring up the competitive advantages of your product. Get their gears turning: Maybe it’s time for them to consider a new tool? If your company offers a free trial, encourage them to compare product features and ease-of-use.

If a prospect tells you it’s not the right time, there’s an implication that there is a right time in the future. Overcome bad timing objections by leaning on urgency.

Are there short-term and long-term effects or business impacts you could reference? Do you know anything about the company’s trajectory? Have their competitors recently raised capital or launched a new product? Does their industry have new regulations or protocols they need to follow?

Do whatever you can to make now the best time.

If someone says to reach back out in 3 or 6 months, Ingram recommends asking “What is going to change between now and then that is preventing you from taking this meeting now?”

Then, after they tell you the reason, ask this as a follow up: “Are you looking to evaluate and implement in 6 months?”

If your prospect tells you they aren’t the right person, there are a few different ways to handle the objection.

If your prospect passes you to someone more junior, elevate your pitch. Get above the line by replacing features and functionality with hard ROI stats, percentages, and dollars.

If your prospect passes you up the chain, that’s great. However, stay in touch with your current contact. They may become an important internal champion for your product when it’s time to face the buying committee.

And finally, if the prospect redirects you to a new department, go back and revise your messaging — it’s clearly not landing for your target persona.

Buyers always say they don’t have budget — but that doesn’t stop deals from getting signed. When you’re hitting financial objections, there are a couple routes you can take.

The first is to ignore pricing and align on pain. Show you understand their challenges, empathize with their struggles, and offer to take it from there.

If the pain point is large enough, chances are they can find budget somewhere.

The second strategy is to have prospects anchor on a price point. Ask them how much they would pay. Once you have a figure, you can work them upward by demonstrating value and impact, including sharing case studies with similar pain points and/or in similar industries.

Don’t see ‘no’ as a total rejection

Even the best sales reps at the best companies get hung up on more often than they have successful conversations.

But what makes you a great sales rep is how you use that rejection.

“Typically when people tell me no that means there are other competing priorities and they have already made an investment into something else,” Ingram says. “So think, what’s the best way to stay top of mind without being annoying?”

In the next few chapters, we’ll talk specifically about strategies and tactics for cold email, phone, and social media outreach. But don’t be afraid to get creative and draw outside of those lines!

Zendesk, one of Sendoso’s customers, leveraged gifting to accelerate deals that got stuck. They sent hundreds of prospects movie kits with a branded blanket and saw a 15X ROI, as well as a 2,000% quarter-over-quarter increase in new business pipeline generation attributed to direct mail.

The backbone of the best cold outreach campaigns: Cold email.

The flip-side of a cold call (where you’re asking prospects to react in the moment, answer questions, and talk to you), is the cold email — where instead you’re giving them a chance to read, digest, and click to dig deeper. Calls and email go hand-in-hand for an omnichannel approach by appealing to the ICP who wants more info before talking.

Automated sales platforms have driven an explosion in the number of emails sent and received. Global email traffic is up to 333 billion emails sent and received per day — and is forecast to keep growing at about 4% per year through 2026.

Even though our inboxes are getting busier, B2B buyers still prefer email over other channels for all phases of the buying journey. About 77% of B2B buyers prefer to be contacted over email — more than double compared to any other channel.

Ryan Freeman, Senior Sales Manager at Calendly, shares that cold emails can be a revenue generator. While some cold emails are ignored, or worse, the prospect unsubscribes, they can also lead to new customers. By testing messaging you can determine what resonates best and leads to booked meetings. “Our approach is to not sell Calendly in our messaging but sell the benefit of an initial meeting with us. Ideally, we uncover individual or company priorities in our research and convey benefits to them. A simple (well written, researched, and message-tested) cold email can absolutely result in a big win.”

Regardless of buyer preferences, getting your email read is tough. The explosion in global email traffic has turned inboxes into battlegrounds.

Today’s reps must make it past their prospect’s spam filter, which is no easy task. Then those emails have to duke it out with hundreds of competing messages. Even when a prospect clicks into an email, there’s no guarantee they’ll read or respond to it.

Despite the immense challenge, reps are cutting through.

Here’s what it takes to be heard.

A cold-email template that delivers

A good cold email earns the prospect’s attention and gets the conversation started.

Perhaps the prospect tells you they’re not interested, but includes an explanation why. Or maybe they’ll say what you’re selling isn’t a priority right now. If you’re lucky, they’ll bite and kickstart a sales-focused conversation.

Those are all positive outcomes. They can all lead to productive sales conversations. When you shift the purpose of a cold email to starting a conversation, rather than securing a meeting, you can redesign your template to be simpler, more open, and less salesy.

Fundamentally, all cold emails rely on four elements:

1. Subject line: Earn attention and generate enough interest for your prospect to open the email.

2. Personalization: Pique their interest with something that only applies to your prospect.

3. Relevance: Demonstrate subject matter expertise and empathy with your prospect’s challenges.

4. Call-to-action (CTA): Prompt your prospect to engage in the conversation.

Pro tip

Often, your first email with someone is a conversation, not a request for a meeting. However, always include your meeting link in your email signature so it’s easy to find. There may be some prospects who are ready to engage right out of the gate.

This email framework is flexible. You can adapt it for different sales plays — referral introductions, event follow ups, even inbound.

But we’re talking about cold outreach. You’ve never spoken to this prospect. You have no connection to them.

Busy decision-makers receive hundreds of emails a day. Your first job is to entice them to open your email. Speak to their limbic system — the emotional part of the brain. Use an emotional hook to bypass rational thought and engage them with something personal, urgent, or important.

So how do you warm them up? Use these questions to inspire your subject line:

• Do you have a mutual connection or referral? Namedrop.

• Did they recently get promoted or did the company share a big piece of news? Celebrate it!

• Is there a new standard or regulation released for the industry? Mention you have expertise in that area.

• Do you want to show that you understand their needs? Prove how you can make an impact or highlight the pain point.

• Is humor effective for your audience and your brand? Craft something funny (while still remaining professional).

Personalization

Here’s the truth: Personalization isn’t going to win you deals. But what it will do is earn your prospect’s attention and build a relationship.

Pro tip

Make it about them. Pronoun-heavy emails read as more personal. Even when they’re automated. Top reps use “you,” “your,” and “your team” 29% more often than their average and underperforming peers.

Jed Mahrle categorizes his prospects into niche buckets: new jobs, hobbies, geographies, technology stack, and more. By using standardized snippets, Mahrle can deliver a personalized feel without spending hours hunting for the perfect snippet.

Just as with cold calls, this is where you’ll make your money. Your relevancy element must prove you know your stuff — challenges, pain points, and goals.

"Personalization is everything. The people I reach out to receive hundreds of emails and calls per day so it’s important to stand out. If they mention anything personal on their LinkedIn such as hobbies and interests, it helps me better personalize my outreach. One thing I’ve seen success in is creating hand-drawn cartoons for prospects. I’ll find their LinkedIn profile, draw a caricature of them, and tie it back to Gong or what I think they may care about.”

When your prospect reads your email, they should be thinking, “This rep really gets me.”

Don’t aim for a meeting in your first email. Instead, use your CTA to learn more. Your goal is to get your prospect talking about their challenges. When they open up and start talking, that’s when you go for the meeting.

But eliciting any response usually takes more than one email.

So let’s talk about sequences.

Multi-email sequences

Considering the wide variety of factors mentioned above, let’s assume the average cold email response rate is 1%.

With such low engagement, it can feel like you’re writing emails no one will ever read.

But so what?

If no one responds to your first email, what about your second or third?

When you build a three-email sequence, the average response rate jumps to 9%. When you expand it to seven emails, response rate spikes to 27%.

The message is clear: perseverance is king.

But for the most impact, you have to tweak your approach.

“If people aren’t going to respond to your first email, what if you used your first email just to set up your second email?” Batrawy says. “What if you used your emails like a string of short stories? Instead of me giving you the entire play in the first email, I’m just going to give you the first act.”

Gong analyzed more than 300,000 cold emails to create 7 Irresistible Cold Email Templates so you can update your sales cadence now.

Here’s a sneak peek of email template No. 1:

Why Gong’s emails work

Choose one ultra-specific message. It will make your outbound efforts more productive. Instead of asking your prospects to do the work and find their area of interest in your email, you can give more context and multiply the impact of your prospecting emails.

Words like “you,” “your,” and “imagine” boost your win rates. Get the full list & data.

Asking for interest is 2X more effective than asking for time in cold outbounding. Here’s the data:

Cold-emails: ask for interest, not the meeting

Source: Calendly

And here’s where you can download the other six email templates in Gong’s sequence.

The first email tees up the problem.

The second email takes a proper swing at it.

With this multi-email storytelling strategy, you just keep going. Your third email builds on your second. Your fourth builds on your third. And so on.

Calls-to-action

When you’re running multi-touch sequences, prospect engagement is not equal across all emails. In reality, response rate follows a bell curve.

Your first one or two emails rarely provoke a response. Likewise, your final touches are unlikely to succeed where earlier emails failed.

Great sales conversations live in the middle.

If you know you’re most likely to generate a response in your middle touches, that’s where you put your most direct CTAs.

"The peak of your message should happen mid-sequence. All messaging before should start off light and be a lead into a stronger ask, while all messaging after should be wrapping up communication, as they may not be ready to buy yet.”

Here’s an example of a five-touch sequence peaking on the third email:

• Email #1 CTA: Does that sound familiar to you?

• Email #2 CTA: Would you be interested in seeing a lesser-known way to handle that?

• Email #3 CTA: Would it make sense to set up 15 to 30 minutes next week to talk about this further?

• Email #4 CTA: Is this something you handle, or is there someone else on your team I should message about this?

• Email #5 CTA: Is it fair to assume this isn’t the right time? Should I follow up in six months?

Notice these are soft asks. Even the third CTA only asks if it would make sense to book time for a meeting.

Once you have their consent, make it as easy as possible for your prospect to schedule time with you. Send your Calendly link, and ask if they prefer to send you some available times. Create soft language around the link. Make it clear that you’re sending your Calendly link for their benefit, not yours.

In Calendly’s emails to prospects, that typically reads something like:

"Book time with me using the scheduling link here, or feel free to send me some times that work for you."

"I know you’re busy. To avoid email ping pong, here’s my Calendly. Or, if you have a calendar link, please send it my way."

Busy stakeholders really do appreciate the ease of simplified booking. When you can, include some options for meeting dates and times in the actual body of the email to make their lives even simpler.

When your prospect gives you an idea of their availability — even something vague like “later in the week” — a tactic from Mahrle is to proactively book time. Set up the event and drop a disclaimer like “Hold.” So long as you tell them how to reschedule, it comes across as proactive. “You’re not going back and forth trying to find a time,” says Mahrle. “Get it on the calendar. Half the time, it works for them. The other half, they click the reschedule.”

Hyper-personalization

As we mentioned before, personalization isn’t a substitute for relevancy. But it’s still a fantastic tool for cold outreach. It can win a prospect’s attention and kickstart the rapport-building process.

“Personalization is what’s booked me meeting after meeting,” says Emma Carr, who's done sales and competitive enablement for Klue. “My prospect knows I’ve spent the time to write an email tying together their specific roles, potential needs, and pain points.”

During her career, Carr built an informal process for personalization research.

She uses three tiers of personalization: individual, company, and industry. Individual-specific personalization is the most impactful, industry-level snippets are the least, and company personalization sits somewhere in between.

There are different research strategies for each:

• Individual snippet: Social media, personal relationship, CRM contact record

• Company snippet: Sales intelligence, financial reports, news

• Industry snippet: News, reports, competitors

With all three types of personalization, Carr recommends being unpredictable and inventive. She often references recommendations and endorsements from LinkedIn, especially if she knows the other person.

Another suggestion: Make the personalization relevant so it’s not a standalone section.

"Reps go wrong by having a sentence on a prospect’s love of tennis and not tying it back into the rest of the email,” Carr says. “If you can find a creative way to tie tennis to a pain point or create an analogy around the sport, it’s a completely different story.”

Sendoso scores!

After finding out a prospect loved the San Francisco 49ers, Clari SDR Vivianna Vu sent along a biography of famous football player Joe Montana through Sendoso’s Amazon integration. She followed up with a clever email, making her gift relevant, educational, and ultimately a success.

The prospect engaged right away and booked a meeting!

You’re not shouting into the void: Buyers out there need you.

Writing one fantastic cold email is unlikely to land you a meeting. Motivation will get you started but it’s habit, grit, and persistence that secure meetings.

To make your cold prospecting repeatable, sustainable, and scalable, you need something to tie calls, emails, and social together — a sequence, campaign, or blueprint. Many different standardized processes detail how and when to reach out to prospects. For inspiration, check out the Agoge Sequence by Sam Nelson. The 15-step multi-channel sequence is a great starting point for fledgling sales reps.

Experts agree an omnichannel approach (aka multi-thread approach, multi-channel approach) is the right way to go in this economy.

"Just one method of prospecting isn’t enough anymore. You’ve got to get creative with your outreach while still tying that to the value, whether that’s social selling, texting, gift giving, or video prospecting. There are so many ways to engage a prospect now than the traditional ways we used in the past.”

In A/B tests, mix it up and test cadence, CTAs, and channels until you find the right formula for your product and your ideal cold outreach prospects.

Remember:

1. Cold outreach isn’t 100% cold if you identify prospects thoughtfully.

2. In uncertain economic times, with the right approach sales reps can overcome tighter budgets and a larger pool of decision makers.

3. Start conversations, not pitches.

4. Place the prospect at the center of those conversations through research, learning about their pain points, job, and company. Get to know them as individuals on LinkedIn.

5. Use an omnichannel approach including email, phone, social (and maybe even some gifting)! Just make sure you’re being heard and your messaging and cadence are on point.

Above all, don’t stop. About 44% of your peers give up after the first message results in silence or a “no.” So if you can mentally push past that, you’re already way ahead of the pack.