Wit and Grit: Crucial Keys to Success for Sales Development Reps

Please pardon my forthcoming self-reference, it’s not a bid for applause but a necessary backdrop. My career has been marked by meteoric growth, from a rookie Sales Development Representative in 2019 to a Director of Demand Generation in 2022, all without the conventional college degree. Some colleagues have labeled me an outlier, a genius even, akin to a rare mathematical anomaly or a lottery winner. However, the reality is more mundane – I’m a person of average intelligence with an above-average tenacity.

Let me set the record straight – success isn’t a game of chance; it’s a deliberate blueprint. Thus, my intent here isn’t to coach you on the perfect cold call script or a persuasive rebuttal, as every Sales Development Representative (SDR) has their unique strengths. Surprisingly, the top performers in B2B sales development often rely solely on LinkedIn and email, coupled with relentless hard work.

I won’t be unraveling a mysterious key to success or sharing an inspirational, yet self-aggrandizing TED talk. Instead, I’ll focus on universally attainable traits: wit, grit, and determination. These are the real engines of success.

The role of a Sales Development Representative (SDR) is one that requires both tenacity and intelligence. It’s a position that demands the ability to handle rejection, maintain a positive attitude, and possess the cleverness to engage prospects effectively. In essence, it requires both grit and wit, among other crucial qualities. Let’s delve deeper to understand why these two qualities are crucial for success in this role.

Grit: The Backbone of Sales Development Success

Grit is the unwavering determination and perseverance to pursue long-term goals. It’s about resilience in the face of adversity and consistency in effort, irrespective of results. Using grit to spark engagement from prospects on LinkedIn involves a combination of determination, resilience, and strategy. Here are some examples:

• Flexibility in Approach: In the world of LinkedIn prospecting, flexibility can be a game-changer. Being willing to work during unconventional hours like weekends, evenings, and holidays can show your commitment and dedication to your prospects. It also increases your chances of catching them when they’re available and more likely to engage in a conversation. This kind of grit showcases your dedication to your job and your willingness to go the extra mile for your prospects
• Actively Monitor Prospect Engagement: A key to successful prospecting is being responsive and proactive. By actively monitoring your prospects’ engagement with emails, you can strategically adjust your tasks based on their actions. For instance, if a prospect opens your email right away, don’t hesitate to call them. If they open your email multiple times, consider setting up an urgent one-off call task. This level of attentiveness shows your commitment to the relationship and your willingness to adapt to the prospect’s behavior. Prospecting becomes more manageable when you use your tools effectively and have a repeatable system in place.
• Leverage an Omnichannel Sales Development Approach: In today’s interconnected world, it’s important to not limit yourself to a single channel when prospecting. An omnichannel approach, leveraging email, phone calls, and LinkedIn, can help you reach your prospects wherever they are most comfortable. Email can be an excellent way to introduce yourself and provide detailed information. Phone calls allow for a more personal touch and immediate feedback. LinkedIn provides opportunities for social selling and building professional relationships. By using these channels in an integrated manner, you ensure your message reaches prospects in the right place at the right time, increasing your chances of success.

 Reasons Why Grit is Essential for Sales Development

1. Long-term Goal Attainment: Grit fosters a long-term vision and the commitment to achieving it. This is crucial for an SDR, as sales cycles can be long and may require sustained effort over time.
2. Increased Resilience: Grit builds resilience, which allows SDRs to bounce back from failures or difficult situations quickly. This resilience can help maintain morale and productivity in challenging times.
3. Enhanced Personal Growth: Gritty individuals are more likely to seek out challenges and opportunities for growth. This can lead to improved skills and performance as an SDR.
4. Improved Problem-Solving Skills: Grit encourages tenacity in problem-solving, a valuable skill when dealing with complex sales scenarios or overcoming obstacles in the sales process.
5. Higher Sales Success Rate: Grit can lead to higher success rates in sales. The perseverance and determination that come with grit often result in improved sales outcomes.
6. Building Strong Customer Relationships: Grit enables SDRs to put in the time and effort needed to build strong, long-lasting relationships with customers, which is key to success in sales.
7. Motivation and Drive: Grit instills a level of self-motivation and drive that can propel SDRs to go above and beyond, leading to better results and higher job satisfaction.
8. Better Adaptability: Gritty individuals are better at adapting to changing circumstances and maintaining their focus on their goals, a critical ability in the dynamic world of sales.
9. Career Advancement: Grit can lead to career advancement. SDRs who display grit are more likely to be noticed and promoted due to their perseverance and resilience.

Wit: The Art of Engaging Prospects

Wit, on the other hand, is all about being quick-thinking, creative, and insightful. It’s the ability to think on your feet, use humor effectively, and engage prospects in a meaningful way. Here’s why it is an invaluable trait for a Sales Development Rep:

• Breaking the Ice: A witty remark or an insightful comment can help break the ice and make a memorable first impression. It can make the conversation more enjoyable for the prospect, increasing the chances of a positive response.
• Standing Out: In a sea of generic sales pitches, a touch of wit can help an SDR stand out. It shows that they’re not just another salesperson trying to make a quota, but someone who brings a unique perspective and a human touch to the conversation.
• Building Relationships: Wit can also help build rapport with prospects. By making conversations more engaging and less transactional, SDRs can foster relationships that could eventually lead to sales.

Example: Using Wit to Spark a Response to Cold Email

On average, a person receives around 100-120 emails per day. This number can be significantly higher for decision-makers who are often the primary targets of cold emails according to Lavender. It’s important to note that most of these emails are ignored, emphasizing the need for a well-crafted, personalized approach to stand out in a crowded inbox. Here’s a fascinating example of a successful cold email sequence that will not only demonstrate the art of infusing wit into your cold emails but also explain why it can trigger a response from even the most elusive prospect.

First E-mail

Subject: Jim, about (your message goes here)

I’m penning this message from home, clad in sweatpants with a company polo at arm’s length, just in case the boss springs an impromptu Zoom meeting on me.

I’m Mario, I’ve a team of 700+ dedicated experts who are passionate about cricket and dropping the beat after the most incredible buildup.

We practice the dark art of IAM. This complex discipline is something we’re on top of like a bulldog on a chew toy.

The Jedi code forbids attachments but you’ll need some context so an overview is attached.

The Bump: Sent Just Two Hours Later

Subject: RE: Jim, about (your message that went here)

Jim, I was right in the middle of assessing the tone of that previous email while sipping a triple venti, iced, skinny, no whip, hazelnut, double-soy macchiato with caramel drizzle when I realized – oops! I’d forgotten to attach that overview.

Sorry, for the crash landing in your inbox today. Please see the attached synopsis as promised.

Final Email

Subject: RE: RE: Jim, about (your message that went here)

Just making sure my previous email hadn’t fallen through the cracks?

Happy to hop on a quick call and walk you through what we do.

Does anything ring true for you and the team?

Decoding the Success of This Sequence

This sequence has proven its effectiveness with a 93% email open rate, a 47% click-through rate, a solid 34% final reply rate, and a remarkable 0% opt-out rate. It’s crafted to penetrate the clutter, employing cleverness and a dash of creativity to capture your prospect’s attention from day one. How, you ask? Let me break it down:

• Engaging Opening Line: The opening line of your initial email is crucial. In today’s over-saturated inbox, enticing prospects to even click on a cold email is akin to performing a magic trick. Bear in mind, that prospects will see a preview of your email’s opening line, whether on their mobile device or desktop inbox, thanks to platforms like Microsoft Outlook. If your opening line fails to resonate or spark interest, your email will find its way into the trash bin without a second thought. Your opening gambit should be informal and engaging, effectively masking your sales intent.
• Value Offering: While most Sales Development Representatives (SDRs) immediately request a meeting, this strategy doesn’t ask for anything upfront. Instead, it provides genuine value by offering critical information about your company right off the bat. This bold approach not only exudes confidence in your product but also demonstrates understanding and respect for your prospect’s challenges and time constraints.
• Innovative Engagement Pattern: Many SDRs are directed to stick to a monotonous engagement pattern: send a formal email that barely scratches the surface of your company’s culture, offers little to no real value, yet still requests a slot in their calendar. Follow that up with a bumped email reply after 3-5 days. If this sounds effective to you, I’ve got a bridge to sell you. This strategy, however, cleverly presents a human error as an inadvertent slip-up, giving you a legitimate reason to bump your email with a response on the very same day the initial one was sent. Intriguing, isn’t it? Not only will they read the email bump out of pure curiosity after receiving two emails from you in one day, but they’ll also revisit the initial email, pushing the open rate even higher.

Balancing Grit and Wit

While both grit and wit are vital, it’s important to strike a balance between the two. Too much grit without wit can come across as pushy or desperate. Conversely, relying solely on wit without showing determination may give the impression of a lack of seriousness or commitment.

Successful SDRs know when to leverage their tenacity to push through challenging situations and when to use their wit to lighten the mood and engage prospects. They understand that their role is not just about making sales, but also about providing value and building relationships.

In conclusion, succeeding as a Sales Development Representative requires more than just product knowledge and sales skills. It requires the grit to persevere through challenges and the wit to engage prospects effectively. By cultivating these qualities, SDRs can increase their chances of success and significantly impact their organization’s bottom line.