I had a client we were struggling to find the right person for. They had been patient but eventually came to me with a specific candidate they wanted hired. Twenty years of sales experience. Impressive resume. The client was convinced. They rationalised that he would hit the ground running, bring a wealth of experience, and lift the whole team.
Within a week he was turning up to the office drunk and start fights, spoke down at everyone, knew it all, kept loudly demanding more money.
Within two weeks we realised he had not made a single genuine call. Every dial in the system was logged at one second. He was connecting the call to trigger the metrics, hanging up immediately, and adding fabricated notes. Twenty years of experience in how to fake activity while doing nothing. Lucky I have thirty years of experience and saw through it.
This is worse than hiring someone with no experience at all. This is actively damaging our brand and your brand. Every fake call is a real number that now has a record of a bad interaction. Every fabricated note is a lie sitting in your CRM that needs to be undone. There are thousands and thousands of excuses to get out of sales work. Some of them are logical and reasonable.
Research suggests around seventeen percent of employees actively do everything they can to sabotage their employer. In sales, where the work is largely invisible until the pipeline review, that sabotage can run for months before anyone notices.
The Logo Problem
The most common version of this problem is big logo’s on the resume.
Sales success at a well known brand does not mean someone can sell. In many cases it is the opposite. The logo sells itself. The rep shows up, the buyer is already half-convinced, and the objections are softer than anything they would face in a cold market. McDonald’s is a huge logo, you don’t need any modicum of sales ability to sell a Big Mac. People will buy Google Ads from a salt water crocodile.
Then they arrive at your business without the brand backing them. Cold market, buyers who have never heard of you a real mountain of actual sales work to build trust and brand recognition. And they have absolutely not prepared for how hard real sales work is, because they have never actually had to sell. The crutch is gone.
They will tell you the product is wrong, the price is wrong, the market is wrong, like I said there are thousands of excuses to not sell. They will have an explanation for every empty week that does not involve them. And because they have twenty years of experience and you have none, you will gaslight you and you’ll probably believe them, for longer than you should. Meanwhile you the founder is still able to make sales.
We call it the sales recruitment merry-go-round. Q1 Recruitment Q2 Bring them up to speed Q3 Realise they can’t sell’ Q4 Remove them. go Back to the go and do not collect $200,000.
The Black Book Myth
One of the most expensive hiring fantasies in sales with industry experience, has worked at your competitor, and you are quietly hoping arrives with a black book of contacts they can immediately convert into revenue. Salespeople in an industry all tend to follow the same path as each other, but sales is sales. Different industry experience usually brings Greenfield prospecting.
It almost never works. The contacts are in the CRM. They cannot export them when they leave. The relationships that existed were between the buyer and the brand, not between the buyer and the rep. And the rep who tells you they have strong relationships across the industry is telling you what they genuinely believe, right up until they call those contacts on your behalf and find out the relationship was not quite what they thought it was.
I ask CEOs this question regularly. ‘How many salespeople’s personal numbers do you have in your phone that you would actually pick up on a weekend?’ They always laugh. The answer is always none.
The black book does not exist. What exists is a resume that looks compelling because of the logos on it and a candidate who has convinced themselves, and now you, that the relationships belong to them rather than to the companies they built them through. Hire for that and you will spend the first six months waiting for a pipeline that is never coming.
What Experience Actually Brings
Experienced salespeople are often jaded. Years of rejection, bad management, broken commission structures, and promises that did not materialise have calcified their thinking and attitudes. They go through the motions because the motions are automatic. But the genuine curiosity that closes deals, the real interest in the buyer’s problem, left the building years ago.
Salespeople are master manipulators and they become masters in how to fake it. Every shortcut, every metric manipulation, every way to look busy while doing nothing. They learned these at the last place, and the place before that and all the other crappy salespeople they worked with had a bunch of other shortcuts. They are not even conscious of it anymore. It is just how they work.
The most dangerous words in sales are ‘I know’ and ‘let me tell you’. A salesperson who thinks they know what the customer needs before the customer has finished their sentence is not selling. They are performing. Sales is a science. You theorise, test, understand, record, analyse, and pivot. You approach every conversation with genuine curiosity about this specific buyer in this specific situation. Calcified thinking does not do that.
They used to say in the army, there are two type of soldier, the ones that say ‘what can I do for the army’, and the ones that say ‘what can the army do for me?’ Well salespeople are the same. Experienced sales people often lord it over everyone. The junior reps, the support staff, the clients. They are the main character and everything exists to serve their narrative. I want this, this, and this.
Company’s that need a good salesperson can’t afford them
To be fair, a truly experienced salesperson is a rare and valuable thing. They trust the process when everything feels like it is falling apart. They have the thick skin that only comes from years of rejection and they know that a bad week is just a bad week. They understand the game at a level that takes years to develop and cannot be taught in a classroom.
The problem is they represent probably two percent of salespeople. The ones who have genuinely been through the fire, stayed curious, still pick up the phone, kept developing, and come out the other side as elite operators are extraordinarily rare. And when you find one, their salary expectations reflect that, the ROI calculation gets very tight very fast for most small and mid-sized businesses.
Most salespeople burn out after five years; interestingly the ones who last tend to be introverts, the ones who can process rejection internally rather than externalise it, who find genuine interest in the craft rather than feeding off the energy of the room. They are not who most people imagine when they picture a great salesperson. But they are the ones still standing a decade in.
The Real Problem Is the Calcified Mind
As children we have elastic thinking. There are few certain things. As we age we get calcified thinking. Think of a child burning its hand. Before it burnt its had fire could be many wonderful things. After burning their hand they came to a certainty, something calcifies in their mind. They now know that fire is hot.
A salesperson who has been doing this for twenty years believes they know many things from experience. They are a liability if they are not comfortable in the chaos. Because the market they learned in does not exist anymore. The buyer they were trained to sell to has been replaced by someone who has already researched your product, compared your competitors, asked AI for a recommendation, and formed a view before your rep opens their mouth.
The cold calling playbook from 2010 does not work the same way. The email sequences that converted in 2015 are hitting spam filters and generating unsubscribes. The LinkedIn approach that built pipelines in 2019 is now the thing everyone complains about. Every channel, every technique, every assumption about how buyers behave has shifted, and it is shifting faster now than at any point in the history of sales. We need to bring genuine curiosity to every conversation, be willing to throw out what worked last year if the data says it is not working now.
Experience is only valuable when it is attached to a an elastic mind and detached from the pride of experience.
The Best of Both Worlds
Experience matters enormously in sales. The thick skin, the pattern recognition, the ability to read a deal and know instinctively where it is going, experience with campaigns and industry, that stuff is real and it takes years to develop.
The problem is not experience. The problem is experienced sales reps are really expensive.
When the actual purpose of the job is to make money, a high cost of sale is counter-intuitive.
At Outsold we solve this differently. Our senior pod leads bring fractional sales leadership, the training, the recruitment, the management, the mentoring, the pattern recognition, the market experience. The stuff that an early stage or growing business needs but cannot justify or afford as a full time hire sits at the top of your sales function setting the strategy, coaching the team, and holding the process accountable.
Underneath that you get hungry, coachable people who are still curious and hungry.
The experienced mind guiding the process. The hungry rep doing the work. That combination, delivered in a light fractional model that scales with your business, is what most founders are actually trying to build when they post a job ad for a senior salesperson with twenty years of experience who will work for a junior salary.
That person does not exist. But we do.
If you are building a sales team and want to understand what the right profile actually looks like for your business and your market, that is exactly the conversation we have with clients at Outsold before we place anyone. You can read more about our approach to outsourced sales, sales recruitment, and fractional sales management in Australia at www.outsold.com.au/blogs.
