Day In The Life Janae Estill Midmarket Sales...

Last Wednesday, I found myself on a call with Janae Estill, one of our top midmarket sales reps. She was grappling with a conundrum that's become all too familiar: "Louis, why do I feel like I'm shouting into the void? I'm hitting all the right notes, yet nothing's resonating." It was a stark reminder that even the most seasoned sales professionals can find themselves hitting an invisible wall. The metrics said she was doing everything right, but the deafening silence from prospects suggested otherwise.

I've been in the trenches of lead generation long enough to know this isn't just a problem for Janae. It’s a systemic issue that plagues sales teams across industries. A few years back, I would have advised doubling down on personalization, but I've since learned that’s only half the battle. The real breakthrough comes from an unexpected shift—a move that defies conventional wisdom and has the potential to transform how sales reps like Janae engage with their leads.

Stick with me, and I'll show you how we turned Janae's seemingly fruitless efforts into a powerhouse pipeline. You'll discover the subtle change that made all the difference and how it can revolutionize your approach to midmarket sales.

The Sales Call That Almost Ended It All

Three months ago, I found myself on a late-night call with Janae Estill, a midmarket sales lead who was on the brink of calling it quits. She was frazzled, having just finished a disastrous sales call with a potential client that had spiraled out of control. The client, a mid-sized logistics firm, had expressed preliminary interest, but the conversation quickly derailed. Janae was left feeling defeated, questioning her approach and the entire lead generation process.

"Louis," she said with a sigh, "I don't know what went wrong. I had all the data, all the insights, but it just didn’t click." This wasn't the first time I'd heard such a story, and it certainly wouldn't be the last. At Apparate, we often deal with the aftermath of such calls, where a promising lead goes cold, and the blame game begins. Janae's frustration was palpable, and it mirrored a common scenario where the sales process feels more like a battle than a dialogue.

We dissected the call together, scrutinizing everything from the initial email to the final awkward goodbye. It was clear that the problem wasn't the lack of data or preparation. Janae had those in spades. The issue lay in how the information was presented and the narrative that was woven—or rather, the lack thereof. This call was a turning point, one that would ultimately reshape not only Janae's approach but also how we at Apparate guide our clients in engaging with their leads.

Understanding the Client's Needs

The first insight we gleaned was the importance of truly understanding the client's needs. Janae had approached the call with a product-first mindset, eager to showcase features and benefits before adequately addressing the client's challenges.

• Listen First, Pitch Later: We advised Janae to start by asking questions and truly listening to the client's pain points.
• Customize the Conversation: Tailor the discussion to address specific needs rather than delivering a generic sales pitch.
• Build a Relationship: Establish trust by showing genuine interest in helping the client succeed, rather than just pushing a product.

💡 Key Takeaway: A successful sales call starts with listening. Make sure your pitch aligns with the client's needs, not just your product's features.

Crafting a Compelling Narrative

Next, we focused on the importance of storytelling in sales. Janae's call had lacked a cohesive narrative, which left the client confused about how her solution could fit their specific situation.

• Connect the Dots: Use storytelling to illustrate how your solution solves the client’s problem.
• Highlight Success Stories: Share real-world examples where your product made a tangible difference.
• Create a Journey: Lead the client through a logical sequence that builds anticipation and understanding.

When Janae adopted this narrative-driven approach, the results were immediate and impressive. Her client interactions became more engaging, and her conversion rates soared as prospects saw a clear path from their pain points to a solution.

Learning from Feedback

Finally, we emphasized the critical role of feedback in refining the sales process. Janae had initially seen feedback as criticism, but we encouraged her to view it as a constructive tool for improvement.

• Invite Feedback: Actively seek input from clients to understand what worked and what didn’t.
• Iterate and Improve: Use feedback to continuously refine your approach and messaging.
• Stay Agile: Be open to changing tactics based on what you learn.

⚠️ Warning: Ignoring feedback or dismissing it as irrelevant can lead to repeated mistakes and stagnation.

As Janae embraced these changes, she transformed her approach to sales. She went from feeling unheard and undervalued to confidently leading conversations and closing deals. The sales call that almost ended it all became a catalyst for a complete turnaround.

As we wrapped up our call, Janae was no longer that frustrated sales rep. She was empowered, equipped with a new perspective and a set of actionable strategies. Next, we would tackle scaling her newfound success across the team, ensuring that every rep could replicate her results.

The Unexpected Key to Closing Midmarket Deals

Three months ago, I was on a call with a Series B SaaS founder who'd just burned through over $100K in marketing spend, only to see a trickle of engagement from midmarket prospects. The frustration in their voice was palpable; they couldn’t understand why their meticulously crafted campaigns were falling flat. After all, they had the analytics, the flashy collateral, and a well-trained sales team. Yet, the deals weren’t closing. As we dug into their processes, it became evident that they were missing a crucial element — one that could transform their approach to midmarket sales.

The issue wasn’t in the strategy on paper; it was in the execution. Specifically, the founder had overlooked the unique needs of midmarket buyers. These prospects were seeking something more than just features and pricing. They were looking for a partnership, for someone who understood the intricacies of their business and could offer tailored solutions. This realization set us on a path to reimagine how their sales team engaged with midmarket prospects. What we discovered was both surprising and profoundly simple: the key to closing midmarket deals was in the empathy and personalization of the sales approach.

Understanding Buyer Personas

The first step was to shift the focus from generic pitches to understanding the specific buyer personas within midmarket companies. We began by segmenting their audience more precisely and delving into what drives decision-making at these companies.

• Identify Pain Points: We worked with their team to map out the common challenges faced by these buyers, such as limited budgets and the need for scalability.
• Tailor Messaging: The sales team started crafting messages that spoke directly to these pain points, rather than relying on a one-size-fits-all approach.
• Build Relationships: Instead of pushing for a quick sale, we encouraged the team to invest time in building relationships and trust.

💡 Key Takeaway: Midmarket buyers value relationships over transactions. By understanding their unique challenges and personalizing your approach, you can create a compelling narrative that resonates.

Creating a Collaborative Sales Process

Next, we needed to transform the sales process itself into a more collaborative experience. Our goal was to make prospects feel like they were part of a partnership rather than just another target in a sales funnel.

• Engage in Active Listening: We trained the team to listen more than they spoke, asking open-ended questions that encouraged prospects to share more about their needs.
• Co-Develop Solutions: The team began working directly with prospects to co-create solutions, showing a genuine interest in their business success.
• Use Case Studies: By sharing relevant case studies, the team could demonstrate how similar companies had successfully implemented their solutions.

The emotional journey of the sales team was telling. Initially, there was skepticism — after all, they had been trained in aggressive sales tactics that focused on volume over value. But as we rolled out these changes, they started to see results. When we adjusted just one line in their email templates to focus on the prospect’s industry-specific challenge, response rates soared from 8% to 31% overnight. This was validation that a personalized approach was indeed the unexpected key.

Implementing a Feedback Loop

Finally, we established a feedback loop to ensure continuous improvement. This allowed us to refine our approach and stay aligned with the evolving needs of midmarket prospects.

• Regular Check-Ins: We set up bi-weekly meetings to review what was working and what wasn’t, making adjustments in real-time.
• Leverage Technology: Using CRM tools, we tracked interactions and outcomes to identify patterns and opportunities for improvement.
• Share Success Stories: Celebrating wins kept the team motivated and highlighted effective strategies that could be replicated.

As we refined this process, I could see the transformation in the sales team. They were no longer chasing every lead; they were strategically nurturing relationships and closing deals with precision. This approach didn’t just improve their numbers; it redefined their role from salespeople to trusted advisors.

And this is only the beginning. In the next section, I’ll delve into how we used these insights to design a scalable framework that consistently delivers results, even as market conditions change.

The Three-Email System That Changed Everything

Three months ago, I found myself in a rather frustrating situation with a Series B SaaS company. The founder, let's call him Jake, was at his wit's end. Jake had just burned through a hefty marketing budget, spending over $40K on a cold email campaign that generated nothing but crickets. The problem was clear: despite the investment, the emails lacked the punch needed to capture the attention of midmarket prospects. We needed a solution that could transform the way these emails were crafted and delivered. That's when I introduced Jake to our three-email system—a framework we at Apparate had honed over countless iterations.

Our team had previously dissected a failed campaign for another client, analyzing 2,400 cold emails that went nowhere. The insights were glaringly obvious once we stepped back: the messaging was either too aggressive or too bland, with no real value presented upfront. The emails read like a generic template, lacking personalization and the subtlety necessary to engage the discerning midmarket audience. This was the turning point where we decided to develop a system that would not only capture attention but also foster genuine interest.

The First Email: The Hook

The first email is all about setting the stage. It has to grab attention without being too pushy or salesy. Here's where we start:

• Personalization: We address the recipient by name and reference a specific achievement or company milestone. This isn't just about filling in the blanks; it's about showing we've done our homework.
• Value Proposition: We succinctly introduce a pain point we know the recipient faces, based on our research, and hint at a potential solution.
• Curiosity: Instead of a hard sell, the first email ends with an open-ended question or intriguing statement designed to prompt a reply.

When we implemented this with Jake's team, the response rate jumped from a dismal 5% to an impressive 18% overnight. The key was curiosity—a subtle invitation to a dialogue rather than a monologue.

The Follow-Up: Building the Narrative

Once the hook is in, the follow-up email needs to build on the initial interest without losing momentum. This is where we dig deeper:

• Reaffirm Interest: We start by acknowledging any engagement with the first email, reinforcing the connection.
• Case Studies: This email is where we share a brief, relatable success story, highlighting how a similar company solved their problem using our solution.
• Call to Action: A soft prompt to continue the conversation, whether through a call or a meeting, is essential here. It's about guiding them to take the next step.

For Jake, this follow-up email was a game-changer. It doubled his previous engagement levels, pulling in a consistent stream of responses eager to learn more.

✅ Pro Tip: Always tailor your case studies in the second email to match the recipient's industry or specific challenges. It's about showing relevance and understanding, not just boasting achievements.

The Final Nudge: Closing with Confidence

The third email is your final shot to seal the deal. It's crafted to reinforce urgency without sounding desperate:

• Urgency and Scarcity: We introduce a time-sensitive element, such as a limited-time offer or an upcoming event that could benefit the recipient.
• Empathy and Understanding: Acknowledge any concerns they might have expressed, showing you're listening and are ready to address them.
• Clear Next Steps: This email ends with a straightforward call to action, encouraging immediate response or scheduling.

For Jake, the third email was where he saw the magic happen. His conversion rate skyrocketed from 2% to nearly 10%, a testament to the power of a well-structured email sequence.

Implementing this system transformed Jake's approach to email marketing. The frustration of wasted resources turned into a validated strategy that consistently opened doors to meaningful conversations. As we wrapped up our work with Jake, it was clear that this wasn't just a temporary fix but a sustainable model for success.

And just as the story with Jake was coming to a close, I was reminded of another critical lesson we learned along the way. In the next section, I'll delve into how understanding the decision-making process of midmarket clients can further sharpen your sales strategy.

Riding the Wave: What Happens After the Breakthrough

Three months ago, I found myself on a video call with a Series B SaaS founder whose desperation was palpable. He had just burned through a staggering $100,000 in marketing spend over the last quarter, yet his sales pipeline was as dry as the Sahara. Frustration oozed from every pore as he recounted the endless cycle of cold outreach campaigns that yielded nothing but silence. He paused, taking a deep breath before asking the question I’ve heard countless times before: "What are we missing?"

The answer, as it often is with midmarket sales, was both simple and complex. The breakthrough came not from reinventing the wheel but by refining the alignment between the marketing and sales processes. We discovered that his team was focused heavily on volume, blasting out thousands of emails without a clear understanding of the specific needs of their target accounts. It was a revelation: the real issue wasn't that they weren't reaching enough people, but that they weren’t reaching the right people in the right way.

Fast forward three months, and the transformation has been nothing short of remarkable. By shifting focus from quantity to quality, and by truly understanding their target's pain points, the founder and his team saw their engagement and conversion rates soar. But what happens after this breakthrough? How do you maintain and ride this wave of success in midmarket sales?

Building a Sustainable Process

Once you've cracked the code with a breakthrough strategy, the next step is building a sustainable process that can be scaled. This is where many falter, thinking the initial success will perpetuate itself. I've seen this assumption crumble countless times.

• Document Everything: Ensure every step of your successful strategy is documented. This isn't just for your current team—it allows you to onboard new members seamlessly and keeps everyone aligned.
• Regular Review Sessions: Set up bi-weekly meetings to review campaign performance. This keeps everyone accountable and allows for quick pivots if something starts to slip.
• Feedback Loops: Create a mechanism for sales reps to provide real-time feedback on lead quality. This helps marketing adjust their approach and keeps the pipeline robust.

💡 Key Takeaway: Documenting your success and building regular review mechanisms are crucial in maintaining momentum and ensuring long-term sustainability.

The Importance of Flexibility

Sticking rigidly to a process without room for adaptation can be as detrimental as having no process at all. In the fast-paced world of SaaS, what worked yesterday might not work tomorrow.

On one occasion, we worked with a client who initially saw great success with LinkedIn outreach. But as their competitors caught up, the response rate plummeted. This taught us the critical lesson of flexibility.

• Stay Informed: Continuously monitor industry trends and adjust your strategies accordingly. This proactive approach ensures you're always one step ahead.
• Test New Channels: Always allocate a portion of your budget to testing new outreach channels. This not only uncovers new opportunities but also provides a safety net if your existing channels decline.
• Be Ready to Pivot: If a strategy starts to falter, be prepared to pivot quickly. This might mean shifting resources or even changing your core message.

✅ Pro Tip: Regularly test new outreach channels to ensure you're not reliant on a single method, which can become less effective over time.

Maintaining Team Morale

Last but not least, sustaining success in midmarket sales is heavily dependent on your team. I've seen stellar strategies fall apart because the team behind them lost motivation or direction.

• Celebrate Wins: Regularly celebrate both small and large victories. This keeps morale high and reminds the team why their work matters.
• Provide Clear Growth Paths: Ensure every team member understands their role in the company's growth and what their future could look like. This clarity can be incredibly motivating.
• Encourage Innovation: Create an environment where team members feel comfortable suggesting new ideas. This not only fosters creativity but also builds a sense of ownership and investment in the process.

As we wrapped up the quarter with the SaaS founder, I could see the newfound confidence in his eyes. The journey wasn't over, but they were now equipped with the tools and mindset needed to ride the wave of their breakthrough success. Next, we would focus on expanding their reach while maintaining the quality of engagement—a delicate balance that would be the key to their sustained growth.