My first job out of school was as a salesperson at Groupon. I learned a lot and believe the training I received was critical to starting my own business and growing my company.
With experience on both sides – as a salesperson promoting the brands they represent and as a prospect being pitched by other brands – I have a lot to say about what makes an effective (or ineffective) pitch.
Here are actual sales pitches I’ve received, why they never work and what to do about them.
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1. You acted patently dishonestly
Weekly newspaper
What are they doing wrong:
They get some points for prominently mentioning customers on BlogSmith, but they should stop there.
The statement that “my team spent days preparing a personalized sales strategy” is a blatant lie. It takes hours or days to get into cold sounds for the first time, which is not a scalable approach at all.
If they do take any time to do so (not recommended), they should at least send out a sneak peek or teaser to encourage calling.
Propaganda like this reads like an attempt to create insincere reciprocity.
It’s like they’re trying to make the recipient think they should spend time creating custom policies that were never asked for or agreed to. They put the cart before the horse and try to force the recipient into the meeting.
How to do:
Never make empty promises – people will come back to bite you when they ignore your sales email or use it as a poor example of a sales pitch in a Newsweek article.
When I’m feeling particularly brazen, I ask them to come up with evidence to support claims that I know are blatant lies. As expected, I have yet to receive a satisfactory answer, which doesn’t match the poor first impression they had in the first place.
In fact, this happened when the next salesperson reached out and claimed that one of their clients was familiar with my brand. I asked, “Which customer?” and was asked to schedule a call to get an answer – no thanks!
Weekly newspaper
2. Your pitches lack effective personalization
Weekly newspaper
What are they doing wrong:
“Custom” video promotions are becoming more and more popular. As with the previously mentioned example, the problem is its dishonesty.
The sales guy claimed they made this video just for me, but we all know the only really custom part was when they mentioned my name and the name of my company.
Of course, they went out of their way to show the visuals of them scrolling through my website and social media to a standard pre-recorded tone – very thoughtful.
How to do:
Personalization is a must if you want to cut through the noise of the dozens of sales pitches the average small business owner receives in a week.
To do this, start with a referral template and customize it without overthinking. You can adjust this to:
- Share the names of businesses you have worked with that are relevant/familiar to a particular prospect.
- Share relevant work samples or client results.
- Comment on the brand that was recently mentioned in the media to show that you’ve done some research.
But be warned: failed personalization as a first impression is very hard to overcome.
I’m getting emails with template fields that aren’t replaced (eg, [Add brand name here]) or a direct copy of an email sent to another brand (listing the other brand’s name in full instead of mine).
In the end, the only message I got was that the sales people and the brands they represented were not careful.
3. Let the recipient judge for themselves whether it is suitable
Weekly newspaper
What are they doing wrong:
As a salesperson, it’s your job to help your prospects understand the relevance of your outreach. So it’s rather confusing to see this salesperson asking their prospect to specify the type of work sample they should send.
Nothing in this email helped me decide if they were for me (spoiler alert: they weren’t), so I ended up moving them out of my inbox and into my “annoying emails” folder for For future laughs (and content).
How to do:
Potential clients can tell the difference between a “personalized” template (making you look the best for them) and a genuine, thoughtful, customized outreach attempt.
If you don’t have enough information about a prospect to give them a compelling reason to work together, consider starting with a different type of email. For example, use standard methods to provide an outline of your value proposition and invest more time in personalizing follow-up emails.
Know the ideal use cases for your brand and avoid red flags for your emails. Take a moment to identify potential clients before reaching out, rather than spamming random contacts. Outreach without purpose is not a sale—it’s a waste of everyone’s time.
extra tip: In general, every sales email should have a clear and easy-to-action call to action.
4. You rely on automation without human involvement
Weekly newspaper
Weekly newspaper
What are they doing wrong:
Timing is everything. The fact that this person asked me at 4:06 am local time on Sunday if I saw the first message she sent after get off work on Friday (4th of July week, no less) caused a double take .
I suspect she wasn’t planning to deliver these messages at such an inopportune time, but was using some sort of LinkedIn automation tool for prospecting.
This is a prime example of why taking shortcuts is a bad idea for a relationship: She ruined her chances of closing the sale from the very first message, and reinforced that further with follow-up messages.
How to do:
First and foremost, she needs to reevaluate the use of automation.
Second, it’s okay to make some assumptions about your prospect, especially with an understanding of why you’re reaching out to them.
But it would be more effective for her to start her outreach with a conversation so that I would simply answer “yes” (or “no” to quickly disqualify me instead of further wasting her time). For example, “Have you considered selling your business?”
Based on my answers, she would see if it was worth sharing more details or asking more questions. After some back and forth, I might become more engaged in moving the conversation forward.
5. You are sending a service listing, not a referral
Weekly newspaper
What are they doing wrong:
I am sure you have received dozens of emails like this. This is a generic list of services, not a sales pitch (several typos).
How to do:
There is nothing in the email that I can use to decide if I want to work with this person or brand. In fact, I have no idea who they are or who they represent. This was clearly a group post, and it was very inefficient and lacked personalization.
From a content creation standpoint, inconsistent capitalization for each list item raises major red flags. I don’t know why “SEO Discount Offer” is in quotes.
Looking at these things might seem picky. But to me, people who don’t put effort into something as small as editing email don’t necessarily put effort into anything, let alone the service they provide.
Presentations play an important role in building trust. There are always little things that come together to make you appear truly professional.
extra tip: Instead of using a random @gmail.com email address like this salesperson did, use a corporate email or a professionally branded social account to send your referrals.
6. You Treat Recipients Like Your Personal Secretary
Weekly newspaper
Weekly newspaper
What are they doing wrong:
This is another example of automation or laziness making mistakes. This attempt is especially embarrassing because my email address starts with my name. So they basically emailed me and asked me to forward this sales pitch to… myself.
Aside from this obvious faux pas, I’m also offended at whether this inquiry was intentional. I am the founder of the company, not their personal secretary.
In fact, he made the wrong assumption and instead of treating me like a decision maker, I actually marked the course for death upon arrival.
How to do:
Assuming the salesperson correctly believes that I’m the gatekeeper to the decision makers they want to meet with – what did they say to convince me to help?
When it comes to sales success, with every contact, you have to be able to answer the question, “What’s in it for me?” on behalf of the prospect.
Every once in a while, I have fun answering some particularly bad emails – here’s my response to it:
Weekly newspaper
I never got a response. Shocking, right?
7. You display a surprising lack of confidence
Weekly newspaper
What are they doing wrong:
There are many problems with this referral email, but the main one I want to point out is the first line: “Hey, very sorry for the cold email.”
Me too.
How to do:
Don’t waste your potential client’s time. If you are unsure whether your offer is suitable for the recipient, please do not send an email. Lack of confidence is downright tiresome and doesn’t get any response anyway.
Step Up Your Sales Email Game
Effective salesmanship isn’t cold and mechanical, it’s about showing empathy and understanding.
While most salespeople are motivated in part by the minimum number of sales campaigns they must meet in order to keep their job, the best reward for a job well done is increasing your earnings through commissions on closed deals.
The most effective path to becoming a well-paid salesperson is to develop a pitch strategy that wastes the least amount of time and effort on the part of everyone involved, rather than spamming every contact you come across.
about the author
Maddy Osman is the author of Writing for Humans and Robots: The New Rules of Content Style. Maddy’s journey from freelance writer to founder and CEO of The Blogsmith has yielded many insights to share about content creation for enterprise B2B technology brands. Her efforts have landed her on BuzzSumo’s and Semrush’s Top 100 Content Marketers and The Write Life’s Top 100 Writer Sites. She has spoken to audiences at WordCamp US, SearchCon, and Denver Startup Week.
