Every organization, no matter its size, success, or stage of growth, is grappling with some form of pain. The small startups face the grind of growing pains, while large corporations get bogged down by bureaucracy. Economically sensitive companies are constantly navigating financial stress. But it doesn't end there—staffing challenges, supply chain disruptions, competitive pressures, political or regulatory hurdles, technological struggles, funding shortfalls, and even the paradox of "too much success" can cause stress within a company. In short, no company is without its unique set of pain points.
As a software sales executive, your mission is to uncover that pain, no matter how well it's masked. While some prospects will share their struggles upfront, more often than not, what they tell you is just the tip of the iceberg—symptoms of deeper, more significant issues. The real opportunity lies in digging deeper, uncovering the root causes, and positioning your solution as the answer to their pain.
In this post, we'll walk you through key strategies for uncovering your prospect's pain points before speaking with them, setting you up to deliver value from the first interaction.
Read the News—Understand the Industry Landscape
The first step is simple but often overlooked: get to know the industry. What’s happening in their world right now? Is there economic pressure affecting their business model? For instance, if interest rates are rising, how might that impact a real estate company’s financing? Or, if healthcare regulations shift, what kind of burdens does that place on hospitals or insurance providers? Understanding industry trends allows you to anticipate the challenges your prospect is facing before they voice them.
A perfect example of this is the passage of the Dodd-Frank Act. While designed to protect consumers, it imposed massive regulatory burdens on financial institutions, forcing them to invest millions in data and reporting solutions. Recognizing such industry-wide shifts gives you a head start in pinpointing potential pain areas.
Here are some industry-specific news sources you can explore:
Healthcare: Healthcare IT News
Finance: Financial Times (FT)
Retail: Retail Dive
Technology: TechCrunch
Automotive: Automotive News
Energy: Oil & Gas Journal
Construction: Construction Dive
Hospitality: Hospitality Net
Agriculture: AgFunder News
Real Estate: Commercial Observer
Customer and Employee Reviews—Find the Gold in the Complaints
Want to know what your prospect’s customers or employees really think about them? Dive into reviews. Customer reviews are a goldmine for spotting recurring issues. While five-star reviews show you what they’re doing well, it’s in the lower-rated feedback where you find the real pain points. Are customers complaining about product delays? Poor customer service? These are areas where your solution might be able to shine.
The same goes for employee reviews. Platforms like Glassdoor provide unfiltered insights into what employees say about their own company. Are there complaints about outdated processes, leadership challenges, or internal struggles? If employees are talking, you can bet these issues are affecting the company’s performance—and that’s where you come in.
Public Filings—Go Beyond the Numbers
For public companies, their financial reports can tell you far more than just their revenue. The 10-Q (quarterly) and 10-K (annual) reports give you a glimpse into the inner workings of the business, from financial health to market position. Look beyond the surface and focus on sections like the Management Discussion & Analysis (MD&A), where executives talk candidly about the risks, challenges, and strategies that can be key indicators of pain.
Here’s what you can learn from these filings:
Audited financials (income statements, balance sheets, cash flow statements)
Management’s insights on financial condition and future risks
Details on competitors, markets, and business models
Risk factors affecting future performance
Corporate governance and leadership dynamics
By analyzing these reports, you’ll often uncover financial strain, strategic gaps, or operational inefficiencies that can lead directly to conversations about how your software can help alleviate the pain. You can find filings for any public company here: https://www.sec.gov/search-filings.
Your Next Step: Become a Pain Expert Before You Even Speak
The most successful software sales executives don't wait for their prospects to reveal their pain—they find it themselves. By researching the industry, diving into customer and employee feedback, and analyzing public filings, you’ll enter your first conversation not just as another vendor but as a trusted advisor.
Challenge yourself: Don’t settle for the surface-level pain your prospect may share. Dig deeper. Ask the tough questions. When you uncover the root causes, you’ll position yourself to offer solutions that deliver real value and long-term impact.
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