How to Reach C Suite Executives in 2021

How to Reach C-Suite Executives in 2021

Scoring consistent sales wins will always be one of the most difficult challenges for sales teams. Even the best-trained professionals will encounter the occasional hurdle on the road to success.  

These days, those issues are even more common. 

Around 70% of respondents in a 2018 Sales Enablement survey said that sales processes are becoming more complicated. New digital channels and unexpected changes to sales in 2020 mean that we’re all struggling to stay ahead of the curve.  

According to sales expert, Justin Michael, sales is actually a game of heuristics. Heuristics are problem-solving solutions that use shortcuts to deliver results. Ultimately, it’s all about having the right information to deliver great results, fast. 

The sales journey doesn’t have to be complicated to succeed. You just need the right blend of ingredients.

The Three Ingredients for Successful Outreach 

If you’re starting to feel like achieving successful sales is a trial and error process, then you might need a new, more consistent strategy for your sales team to follow. 

Today’s reps spend around 40% of their time looking for and creating content to support a sale. 

This strengthens the findings of companies like Hubspot, who found that salespeople spend just one-third of their day speaking to prospects

What does this mean for your sales team?

First and foremost, they need a new playbook. 

Your playbook is the script that your team uses to guide their decisions and use technology more efficiently. Playbooks also deliver more detailed tactics for lead scoring, so reps can spend less time on unqualified leads. 

While every brand’s playbook will differ according to its goals and requirements, there are three key ingredients that you’ll need to think about in this new landscape.  

Personalization: The Empathy in Sales 

For years, personalization has been a key trend for businesses of all sizes.

Throughout the decades, consumers have always given better responses to brands that focus on their individual needs and expectations. Your customers want to know that you understand them, but, both in times of trouble and success. 

Going forward, the demand for empathy and personalization in sales will be even greater. 

Teams need to work harder to show their prospects that they need the items they have to sell. 

Right now, 31% of customers say that they’re not confident marketers are approaching personalization correctly. 

The same issues apply to sales. 

So, how do you embed personalization into the sales playbook? 

More importantly, how do you ensure that you can use those personalization strategies at scale? 

The first step is embracing the right technology. The key to understanding your audience is gathering as much data as you can about their experiences, pain points, and other critical issues. 

Browsing through LinkedIn isn’t enough. 

You need a comprehensive environment where you can curate customer data into meaningful insights. A sales enablement platform that combines things like CRM data, emails, and other essential information is crucial. 

The more data you have, the more personal you can get with your customers. 

Sales enablement tools will help you to divide your clients into different segments based on critical identifiers. For instance, you might have one group for business leaders and another for corporate financial advisors. You might even segment your customers according to their location, or how they prefer to contact your team.

Don’t just mimic empathy by telling them that you understand they have problems. Demonstrate genuine understanding by empathizing with the issues they have right now.  

Relevancy and Clear Messages 

Once you understand who your audience is and what they need, the next step is making sure that all of your presentations and sales efforts are relevant. Relevancy is how you prove to your target audience that you’re not just mimicking the empty gestures of other brands. 

When global disasters strike, hundreds of companies often send emails to customers en masse, trying to get ahead of the issue. These emails seem to have almost no filter: reaching both VIP customers and clients who hadn’t interacted for years, at the same time.

Consumers see these emergency emails as inauthentic and annoying. 

Many of the messages go straight to the spam folder, while some customers block certain companies completely. The only emails that really seem to make a positive impact were the ones that looked at exactly what the business could do to make life easier for their customers. 

In an age where customers want better, more emotional connections with the companies they buy from, sales teams can’t afford to confuse empathy with fluff. Messages need to be short and straight to the point – don’t waste your customer’s time with information they don’t need to know. 

More importantly, focus on the problems you’re solving for your customers right now. 

As Founder of Marketing Think, Gerry Moran states, “good relationships start by putting the other person first.” In other words, the key to real relationships, especially in these trying times is to establish credibility and trust by deeply understanding where the other party is coming from. 

Figure out what kind of problems your audience is facing based on your email messages and CRM information. 

For instance, if someone on your list might be struggling with their finances right now, reach out offering them a payment holiday, or a discount if they’re willing to sign up with your service for longer.  

Use your customer profiles and detailed information to tailor your message to the things that are most important to your audience right now. 

Staying relevant is how you demonstrate the essential nature of your company.  

Get the Timing Right 

Finally, as most sales professionals already know, it’s not just what you say, or even how you say it that matters in today’s landscape. 

You also need to figure out how you’re going to get the timing right too.  

No matter how personalized, relevant, and clear your message appears to be, it won’t resonate the right way if it arrives at the wrong time. 

Your sales playbooks need to provide agents with insights into how they can identify the right time to send an initial message, and how long they should wait before following up. 

Remember, the playbook is there is a guideline, not a concrete set of rules. Agents also need the freedom to adjust the guidelines based on what they know about each customer. 

Getting the timing right has always been a crucial consideration in sales.  

It’s why businesses of all sizes use things like the “buyer journey” to dictate sales and marketing actions. Pushing your client to buy something with a complete sales pitch when they’re still in the consideration stage is rarely a good idea.  

Most sales teams will have a general idea of timing already. The tools you use to manage your sales strategy will inform you when a lead becomes qualified so a rep can reach out with initial contact. After that, you can figure out what the best time might be for a follow-up conversation, based on your previous experiences. 

As the world becomes increasingly digital and connected, you may discover that you can follow up much faster via LinkedIn and social media than you would if you were calling or emailing a prospect. Some teams might even set up consumer Slack accounts so that they can interact with clients whenever they need to in real-time.   

Our research into the emerging sales signals and trends for 2021 found that SMS could be a powerful new tool for outreach. And according to this data, SMS implemented into outreach strategies reduced the number of touchpoints needed to close a deal by 19%. 

Additionally, we also found that more digitally-focused journeys were driving better outcomes. 

The most effective sales journeys centered around a LinkedIn connection first, followed by SMS, then email. 

Agents that approached buyers on LinkedIn before a demo took the customer to the next step of the sales journey 67% of the time. 

The key to success is paying attention to what works for your audience. 

Maintaining a closed-loop environment where you can get frequent insights into the experiences your customers enjoy, (and the ones they don’t), will be essential. 

Feedback from both your clients and your agents will allow you to gradually optimize the sales process to suit different audience segments. 

You can even use the feedback you gather to retain clients, not just attract new ones. Remember, attracting new customers costs up to five times more than keeping an existing client.  

Updating Your Sales Strategy for the New Era 

Mastering sales doesn’t have to be complicated.

If you can find the right blend of personalization, relevance, and timing, you can succeed with a prospect.  

Learning how to build your new sales strategies around these three critical ingredients will help you to close more deals and strengthen your relationships with your target audience, just remember to keep learning as you go. 

Right now, we’re all moving through a period of uncertainty and confusion: the new era of sales will require a certain degree of caution and agility.  

Good luck.  


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  • To understand how I got here today, I am sharing my story of where it began...
  • To understand how I got here today, I am sharing my story of where it began...
  • To understand how I got here today, I am sharing my story of where it began...

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Justin Michael

Justin Michael is the Tony Stark of the 2020s seeking to automate revenue operations and optimize all tech stacks. He's advised over 100 startups in this pursuit and is a Futurist. He will release Tech-Powered Sales in 2021 to highlight how to perform a superhuman scaling.

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