How to win at sales outreach: 5 golden rules for agencies

Effective sales outreach is crucial to agency success. However, the pandemic has disrupted traditional in-person relationship development and forced a shift towards digital communication. This has made email communications a key plank in how sales reps drive interest, engagement, and demand among prospects.

Yet, with overflowing inboxes and time-starved decision-makers, it's becoming increasingly challenging for agencies’ sales representatives to stand out and get noticed. That's why it's essential for agency owners and their sales leaders to adapt and learn new ways to succeed in the digital landscape.

To help agencies improve their email outreach results, we invited Joel Stevenson, Vendasta’s VP of Growth and the former Chief Executive Officer of the sales intelligence tool Yesware (which we acquired in October 2022), to share his expertise at our recent Conquer Local Connect event.

With over 20 years of experience in sales and business development, Stevenson and the Yesware team have analyzed millions of emails and outreach strategies to identify the most effective email outreach strategies.

Here, he outlines five golden rules for using emails effectively in your agency’s sales outreach strategy. By mastering these rules, you can enhance your sales performance and achieve greater success. Watch the video below to learn more or read on for a recap of his keynote.

Understanding the challenges of “inside sales”

To effectively sell in today's world, agencies must understand the challenges associated with remote selling.

The pandemic has upended sales outreach by accelerating the shift towards remote selling through digital channels, which is also known as "inside sales." This approach involves using email, phone, virtual meetings, social media, and other digital channels to sell services rather than relying on in-person interactions.

Despite the majority of the six million sales reps in the US having adopted the inside sales model, many fail to effectively engage prospects due to a generic and unengaging approach to selling services.

“You need to think about inside sales in the same way as a competitive advertising or marketing channel. Just like you would test new copy and creatives when developing and executing ad campaigns for your customers, you need to try new methods to succeed when it comes to inside sales,” Stevenson says.

By taking a data-driven and quantitative approach to inside sales, agencies can avoid wasting their own resources and increase their chances of success.

Golden rule #1: Don’t let good leads go to waste!

"When it comes to inside sales, unforced errors are the worst type of errors, in my opinion," Stevenson says, adding that he has noticed reps tend to make three common mistakes in sales outreach:

  1. Failing to follow up with prospects, which can cause them to lose interest. Stevenson emphasizes that "many sellers are contacting the local business owner, so if reps don't follow up, buyers either lose interest or think that you didn’t get back to them.”
  2. Failing to prepare for meetings with leads. “We work so hard to book a demo with leads, and then I see reps go into meetings without having done their research on the business and the buyer, or come prepared with the right questions,” he says.
  3. Failing to define clear next steps, which can derail the sales process. Stevenson stresses the importance of having a mutual agreement on next steps, whether that's agreeing that it's not a good fit, scheduling a follow-up call, or sending a proposal or demo.

Golden rule #2: Save time and boost productivity with automation

Productivity is key to maximizing sales results. Sales automation can provide a significant boost to your agency’s sales outreach efforts. Instead of wasting valuable time on repetitive tasks such as typing the same email or manually scheduling meetings, agency sales reps should take advantage of automation tools and triggers.

"Repeating the same old routine of back-and-forth communication like it's 1999 is not helpful to anyone," notes Stevenson. Unfortunately, many sales reps still rely on manual processes such as jotting down reminders or trying to recall when to follow up with a lead.

"Keeping track of these tasks can be a real cognitive burden. Thankfully, we can use systems and triggers to automate these processes and get notifications for follow-up actions," he says.

By automating these mundane tasks, sales reps can save time and focus on more important aspects of their job, such as preparing for meetings, understanding their customers' businesses, and crafting relevant questions.

"As an agency owner or rep, you need to shift the focus to preparation and research so that you can have those quality conversations with customers and prospects. That’s where your focus should be on inside sales—not in rewriting emails," advises Stevenson.

Golden rule #3: Scale your targeted sales outreach with the help of technology

As Stevenson notes, "You're never going to convince everyone that your cold email is not spam." However, you can improve your chances of reaching potential customers by leading with value.

“Give prospects something helpful right away and personalize your message to show that you've put in real effort,” he says.

For example, rather than sending generic messages like "We can help you with SEO, check out our testimonials," a good SEO agency should conduct some initial diagnostics and include that information in the email to demonstrate their capabilities to the prospect.

“I’m much more likely to respond to an email where the sales rep has done their research, so give first and lead with value by providing something that’s helpful or insightful right off the bat,” Stevenson says.

“So rather than send mass, generic emails, be very targeted and do the research into the buyer or customer persona, and then use the power of technology, AI, and automation to scale your sales outreach in a way that maintains personalization,” Stevenson continues.

Golden rule #4: Don’t give up (too easily)!

Stevenson emphasizes the importance of “polite persistence” in your sales outreach strategy. According to Yesware's analysis of over 1 billion emails, 42 percent of emails that receive a reply do so within the first hour, and 95 percent within the first day.

However, if you don't get a response within 24 hours, your chances of getting a reply decrease to 1 in 20, he warns.

To increase your chances of success, it's crucial to follow up with multiple touches across different channels such as email, phone, and social media engagement. Yesware's analysis suggests that the optimal sequence is six touches over 14 days across multiple channels—see the below image for the suggested channel of interaction for each touch.

But Stevenson cautions against sending generic "just checking in" emails that add no value during your cadence.

"It's essential to remember the prior rule of giving first or adding value. If all six touches fail to deliver any value then don't expect good results. You need to be giving value in every touch. If you don’t have any value to add, find a way to do so before going back to your inbox," he says.

Golden rule #5: The power of data sharing and how it drives high-performance sales teams

Sharing data among sales teams can be a game-changer, according to Stevenson. If one sales rep in a team of 20 figures out an effective way to move from a discovery call to a demo meeting, the whole organization can benefit by learning from their strategy.

“Maybe it’s a certain approach to follow-up or a certain piece of content. Whatever it happens to be, once that’s figured out and the learnings are shared, then the whole organization can go from a particular stage of the funnel to the next stage at a faster rate. If you’re part of a sales team, everybody wins when data is shared,” he says.

In fact, Yesware’s research on sales team collaboration—highlights of which are shown below—underscores that sales teams that collaborate and share best practices scale faster.

"If you can apply these golden rules to your overall sales outreach strategy, you can achieve a much more efficient and effective sales process than with a generic approach where you don’t collaborate and share learnings within your own organization,” he says.

Frequently asked questions

What is outreach in sales?

Outreach in sales is the process of reaching out to potential clients with the goal of generating leads and, ultimately, making sales. It involves identifying and engaging with prospects through various channels, such as email, social media, and phone calls, to establish a relationship and encourage them to take action.

How to automate cold outreach in sales?

Automating cold outreach in sales can save time and resources while also increasing efficiency and effectiveness. Some strategies for automating outreach in sales include using customer relationship management (CRM), email marketing, and sales intelligence systems to manage and track leads, creating email templates for different stages of the sales cycle and specific verticals, and providing notifications of when to follow up with leads based on how they interact with your messages, such as opens and content clicks.

About the Author

Vishal Teckchandani is a Content Marketing Specialist at Vendasta. A newcomer to Canada, he spent the last 14 years of his career in Australia as a financial services reporter and TV host. He has written extensively about how technology companies are transforming business processes and lives, and interviewed the CEOs of global banking, payments, SAAS, and cloud storage providers including Afterpay, ELMO Software, Macquarie Group, National Australia Bank, NextDC, and Zip Co. When he’s not creating content, Vishal loves to cook, explore Saskatchewan with his family, and volunteer for his community.

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