DO < BETR: SELLING SMARTER IN A COMPLEX WORLD
Meet Sarah. She’s a mid-career salesperson working in enterprise software. Sarah knows her job isn’t just hard—it’s brutally hard. Her territory covers 300 accounts, ranging from scrappy startups to Fortune 500 giants. Her manager wants more meetings booked. Marketing keeps dropping generic campaigns in her inbox to forward. Customers will meet with her if they see value, but she often hears: “I don’t have time or any new budget.” Getting in front of prospective new clients is very challenging and thus she tends to focus on existing customer retention and some cross-sell opportunities that she understands. Her bag of products is heavy, thick, growing and complex.
Sarah’s not lazy or underqualified. She’s overwhelmed, stuck in the trap of trying to do everything. And in today’s hyper-competitive sales environment, that’s a recipe for burnout and likely change.
The problem isn’t Sarah—it’s how she’s being told to sell, what to sell or how she is reacting to the overwhelming complexity of the task. When overwhelmed, we often retreat to what we know or have done in the past. Not a successful recipe in a rapidly evolving world.
The Complexity of Modern Selling
Selling today is less about relationships or persistence—it’s about relevance. The average B2B buyer is bombarded with 10-15 sales pitches a day. Meanwhile, they’re juggling competing internal priorities, endless virtual calls, and shrinking budgets. If your pitch doesn’t instantly connect to their world of immediate priorities, you’re out. “Out” generally means “no response” to whatever reach-out channel you used.
Sarah’s challenge wasn’t her work ethic. It was her lack of focus. Instead of treating her territory as a list of names to call, Sarah needed to prioritize it like a strategic plan. She didn’t need to work harder—she needed to work smarter. That’s where Do < BETR comes in.
The Problem: Selling Without Strategy
Most salespeople approach their territory like Sarah did:
1. Broad Outreach. “I’ve got 300 accounts. Let’s start with the A’s.”
2. Generic Messaging. “We help companies streamline processes and improve ROI.” (Translation: This email could apply to anyone.)
3. Reactive Follow-Ups. “I’ll just check in to see if they got my last email.”
The result? A lot of noise, very little traction, and a pipeline full of unqualified, uninterested prospects.
Here’s the reality: You can’t sell effectively to 300 accounts—or even 50—without a plan. Buyers expect salespeople to understand their business, their role, and their challenges before the first conversation. If you can’t connect your solution to their world, you’re not adding value—you’re wasting their time.
Ideas: Prioritize, Personalize, Hypothesize
Sarah turned things around when she embraced Do < BETR. She didn’t try to cover her entire territory. Instead, she built a plan rooted in three principles:
1. Prioritize the Right Accounts
Sarah segmented her territory into tiers:
● Top 10 Accounts. High-value opportunities where her solutions have a clear fit. These could be new or existing accounts, but she could see the fit and opportunity. These became her focus, knowing she needed to build credible and meaningful relationships with multiple stakeholders.
● Next 20 Accounts. Existing clients and growth accounts with the highest likelihood to need what you sell.
● The Next 20 Accounts. Existing clients and growth accounts worth nurturing for future opportunities.
● The Rest. Accounts with lower potential that received light, automated touchpoints. A good place to test messages, tactics, build skill and confidence.
This prioritization gave Sarah the time and bandwidth to deeply understand her most valuable clients and prospects.
2. Customize Messaging with Purpose
Generic outreach wasn’t cutting it. Sarah stopped pitching products and started crafting messages tailored to each account:
● She researched each company’s industry, competitors, and recent challenges.
● She studied the specific roles she was targeting—what challenges they are dealing with now? What outcomes did they care about?
● She built personalized, value-driven messages that connected her solution to their world.
For example, instead of saying, “We help companies improve processes,” Sarah led with, “I saw your CEO’s recent comments about reducing supply chain costs. This is a complex problem and we often get asked by your peers, “What mistakes do you see companies making as they try to reduce costs?” Here are the top 3.
3. Build a Hypothesis Before Reaching Out
Before making a single call, Sarah created a hypothesis for how she could help each account:
● Step 1: Based on the role she was targeting, she determined their top 1-2 likely objectives, how they would likely try to achieve those objectives and challenges they will face. A bonus step would be to try and understand the quantifiable impact of those challenges and the questions you could ask to quantify or qualify them.
● Step 2: Connect those challenges to her solution and how she is uniquely positioned to help. The goal here is to build credibility around the problem and solution.
● Step 3: Craft an outreach plan across multiple channels—phone, voicemail, email, LinkedIn, and direct mail—with the hypothesis front and center.
By starting with a hypothesis, Sarah wasn’t just selling; she was providing insight. Her outreach became about solving problems, not pitching products.
The Power of Focus
Within three months, Sarah’s results were remarkable:
● Fewer Accounts. More Progress. By focusing on 50 accounts instead of 300, Sarah closed two major deals and advanced conversations with five more.
● Higher Engagement. Personalized messaging led to a 3x increase in response rates compared to her previous generic emails.
● More Confidence. Instead of feeling overwhelmed, Sarah had a clear plan—and it showed in her conversations
Your Challenge: Sell Like Sarah
If you’re a salesperson struggling with too many accounts and not enough traction, here’s how to start:
● Segment Your Territory. Focus on your top 20-50 accounts and deprioritize the rest into more of a quarterly touch providing valuable information.
● Research Relentlessly. Learn everything you can about your targets’ industries, roles, and pain points. Research is scalable across similar accounts and industries.
● Craft a Hypothesis. Build an idea, story and plan that connects your solution to their world before reaching out.
The days of dialing for dollars are over. Success in sales today isn’t about doing more—it’s about doing better. It’s about Do < BETR.
Your clients and prospects don’t need another pitch. They need someone who gets it. Will that be you?