Know What You're Worth - And Who's Willing to Pay for It
The Sales and Career Lessons Hidden in the Old Watch Story
A father hands his son an old watch and says, "Take it to the pawn shop and see what they'll offer."
The shop offers fifty bucks. The son tries a street market - twenty. Finally, they take it to a collector. The response? "This is a rare vintage piece. I'll give you five thousand."
The story's been told a hundred different ways. Its message seems obvious: Go where you're valued. But in sales and career strategy, it runs deeper than that.
This isn't just a fable about self-worth. It's a mirror for the hard truth of value, perception, and market fit.
In Sales: Your Job is to Prove the Value - Not Just Assume It
The watch never changed. The context did. That's how sales works.
If your product or solution is being undervalued, it's not necessarily the buyer's fault. They're doing what buyers do: anchoring low, asking for discounts, pushing commoditization.
It's your job to reframe the conversation.
If you let them compare you to the pawn shop down the road, you'll get the pawn shop price. If you show them you're a category of one - solving a mission-critical problem - they'll bring out a different budget entirely.
Every great Rep knows: The buyer's default mission is to devalue. Your mission is to educate, reframe, and raise the perceived stakes.
The buyer's default mission is to devalue.
Your mission is to educate, reframe, and raise the perceived stakes.
In Your Career: You Might Be the Right Watch in the Wrong Place
What if you're the watch?
You've got years of experience. You've grown pipelines, cracked new verticals, landed seven-figure deals. But your company sees you as just another Rep, just another number in the forecast.
There's no room to move up. Your comp plan punishes instead of rewards. The leadership doesn't play at the level you're aiming for.
It's not that you're overvaluing yourself. It's that your current environment has a low ceiling - and no interest in raising it.
But before you jump ship, consider reshaping your current market first.
Start by documenting your impact differently. Don’t just say you hit quota. Show how you changed the game. “120% of target” is good – “cut CAC (Customer Acquisition Cost) by 30% and doubled ACV (Annual Contract Value)” gets you into strategic conversations."
Present yourself as a revenue operations partner, not just a quota-hitter.
Request stretch projects that position you closer to strategic decisions. Volunteer for the high-stakes prospect nobody else wants to touch. Create visibility with leadership three levels up, not just your direct manager.
Sometimes the same company that undervalues you as "sales Rep" will pay premium rates for "Strategic Account Executive" or "Market Development Lead" - if you can demonstrate the difference.
When Internal Repositioning Isn't Enough
Here's where the watch story gets complicated in real life. Not everyone can simply pack up and find their collector.
Maybe you're tied to a specific geography because of family. Maybe your industry connections are deep but narrow. Maybe the "collector" markets require skills you don't yet have, or certifications that take time to earn.
The story makes it sound easy to walk from the pawn shop to the collector. In practice, there's often a bridge market in between - a place where you can develop the credibility and connections that eventually lead to premium positioning.
The Career Arc: How Strategic Moves Build Market Value
The smartest sales professionals don't just jump between random opportunities. They build a progression - each move adding credibility and market knowledge that compounds over time.
Consider this career arc: mobile sales → enterprise telecom → cloud infrastructure → SaaS platforms. Each transition leverages previous experience while adding new technical depth. More importantly, each step positions you as someone who understands technology evolution, not just current products.
This is where the "groundbreaker" positioning becomes powerful. Companies will pay premium rates for Reps who can launch new products, crack new verticals, or implement untested strategies. Why? Because these initiatives often make or break quarterly numbers, and most salespeople avoid the uncertainty.
If you can build a reputation as the person who turns strategy into revenue, you become the collector's item - not just another watch.
The key is staying 3-5 years in each role. Long enough to show measurable impact and build deep relationships, but not so long that you become associated with legacy approaches. In fast-moving tech, relevance has a shelf life.
Want bigger money? You may need a different market - but the transition can be strategic:
Industries: Move from legacy tech to SaaS, but start with companies that serve both markets
Deal size: Take on enterprise accounts within your current role before switching to an enterprise-only company
Customer profile: Seek out growth-focused buyers within your existing territory
Companies: Target firms where your current experience is rare and valuable, not common
Finding Your Collector: Three Concrete Steps
The lesson of the watch isn't about ego. It's about alignment. Whether you're selling a product or positioning your own career, your value isn't fixed - it's revealed by the market you choose to play in.
But "find the collector" is easier said than done. Here's how to actually do it:
Step 1: Map your value story. What specific problems do you solve that others can't? What outcomes do you drive that matter most to senior leadership? Get precise about this before you go looking for your collector.
Step 2: Research your collectors. They're not always obvious. The collector for your sales skills might be a company scaling internationally, a startup with a complex product, or a traditional business trying to digitize. Study job postings, LinkedIn profiles of successful people in your target roles, and industry publications to understand what these markets actually value.
Step 3: Test the market without burning bridges. Take recruiting calls. Apply to a few stretch roles. Have informal conversations with people in your target markets. You're not committing to anything - you're gathering intelligence about where your watch gets valued at $5,000 instead of $50.
When that market doesn't see your value, your next step is simple: Find the collector. But remember: Collectors aren’t looking for just any watch. They’re looking for the one that completes their collection. Be that one.