It is easy to forget that the biggest winners have had some of their #failures. The most successful people in life are often those who’ve experienced failure, not just they’re successes.

We asked #RevSummit17 speakers to share their most memorable sales failure stories — because learning what not to do is a great complement to learning what to do. 


Sales Fail #1 – Insufficient Prioritization

Tonni Bennett, Terminus

When I was a salesperson at Pardot, there was one quarter when my quota almost wasn’t met. Looking back on it now, the mistake I made is that I didn’t prioritize correctly and understand what late-stage opportunities mean. Instead of focusing on accounts where conversations had been going for the longest amount of time with people who were never buying anything from me (i.e., tire-kickers), I focused more on accounts with potential use cases and strong timelines to implement projects.

Sales Fail #2 – Woes in Pricing

Amit Bendov, Gong.io

It’s that moment when a prospect accepts your proposal, and you know they could have negotiated for more.

I was in charge of sales for a startup and we were still doing inside sales. The perception at the time was that you could only close small deals over the phone, so I wanted to test what would happen if we did bigger deals.

I got a lead that I knew is going to be my six-figure deal. A large company, funded project. A 100K contract would not have been difficult for them at all.

I remember sitting on the phone with their procurement person and he was asking about various parts of our proposal. Nothing major, but I started to get worried when we got near the final section: pricing.

He said, ‘we’ll pay cash so we get a discount.’ But this is often what negotiators do to see if they can try and negotiate the price down for their first sale.

“One quarter of a percent,” he responded.

I thought I misheard. “How much?”

“1/4 of a percent”

And that was it!

I should have raised the price. It’s too cheap.

The key takeaway is that you need to test your assumptions ruthlessly, and not be afraid of failing. The upside may just be worth the risk.

Sales Fail #3 – Management of Lead

Dayna Rothman

I remember when I first started in B2B marketing, and my boss wanted me to host a happy hour event. It was the first time I had ever planned an event for prospects.

I had to tell my boss that I gave the lead bag with business cards to an event attendee and not our swag bag, which was a disaster. He got very angry with me.

We were in a panic, so we sent out an email to the original invite list and offered free gift cards for whoever handed over our lost bag. Luckily someone came forward with it and returned it to us.

A) Keep your leads close. B) Make sure you have a backup event registration method, and C) Pay attention to what’s happening around you.

Sales Fail #4 – Lacking Preparations

Matt Heinz

A few years ago, I went to a meeting without any preparation and hoped for the best.

I met with this company two months ago, but I forgot the meeting. They asked me about their sales and marketing efforts, so I just repeated what they already heard.

It’s easier to say it was because of too many meetings and not enough prep time, but that would be unacceptable. I lost the business.

I now take the time to review my schedule in the morning to be sure I’m prepared for meetings.

Sales Fail #5 – Losing Focus

Julia Stead, Invoca

In the past, we underestimated and undervalued the time and attention it would take to properly compile a list of target contacts for a trade show campaign. We spent lots of time debating messaging and offers but ended up scrambling to put together contact lists with little response rates or junk interest. Now we spend most our time on compiling lists first then getting in front of people with good messages.

Sales Fail #6 – Harsh Rejections

Shep Maher, guidespark

When I was 22, a Mellon Bank CFO called me to set up a meeting. He said that he wanted the service because it would provide investors with more transparency.

I pitched this idea to the CFO and he immediately rejected me. I felt embarrassed, shocked, and ashamed as I crawled out of his office.

It was a great learning experience for me because I learned that no matter how important the person, if your offer is worth it and you’re persistent enough to get in front of them, they will listen.

Sales Fail #7 – Being Too Salesy

Bastiaan Janmaat

My biggest sales fail is that I was too focused on selling my product. For the first year of building DataFox, I always dove straight into a demo without understanding the customer’s needs. I hired our first Sales Rep from Salesforce and he put me through what felt like an intensive bootcamp to whip my need-finding in shape!

Sales Fail #8 – Too Many Emails

Sangram Vajre

I had a lot of trouble with people not responding to me. I found that the best way was phone calls or face-to-face conversations.

Sales Fail #9 – Too Humorous

Richard Harris

When I changed the way I introduced myself to be more humorous, it didn’t go over well in a professional setting.

I had about 4 deals that I thought were going to take off, but they turned out not to be for me.

I switched back to the original system and it started growing again.

Editors Note:

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Justin McGill
About Author: Justin McGill
Justin McGill is the Founder of LeadFuze - a lead generation platform that discovers new leads for you automatically. Get 25 leads free.