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What’s the best sales deal you ever closed?

If you ask any salesperson about the favorite deal they ever closed, they will have a story to tell. They will share stories of guts, perseverance, quick-thinking and clever strategy.

However, the best sales deal stories will also often have a lesson that the salesperson took away from the experience: one which other reps can learn something from as well.

We asked some selling experts to share their stories and the lessons they learned (and you can learn) from them.

Douglas Holly

International Sales Representative at Ciara.

“I once had a guy that briefly visited our website, but was not using our program, nor did he request a demo just to check it out. He was a good lead, meaning their business required regular phone conversations with customers covering the same topics, an inside sales team, etc.

“I reached out by phone and received no response. I left a friendly voicemail and sent him an email with the option to schedule a short demo call. Again, no response.

“A few days later, still nothing, but he had opened my email multiple times. I call again, and he actually answers. I confirmed it was him, informed him who I was and why I was calling. Maybe he woke up on the wrong side of the bed, or if it was the person I could hear literally screaming profanities at him in the background, but he immediately got hot-tempered after I said who I was and why I called.

“He made a rather rude comment before hanging up, but considering his circumstances, I couldn't really blame the guy! Considering what I’d just witnessed, I thought I’d leave that poor guy alone for a while. It sounded like he had plenty of things to handle.

“A couple of weeks later, the guy emails me and sets up a demo call. I give him a short demo of the program describing the various features Ciara has to offer that would help out his team. The next struggle wasn't the screaming in the background (thank God). Rather, it was getting him to realize that Ciara was far more helpful than their current solution, which didn’t connect to their CRM, had horrible outlines for scripts, and no way for the SDR to know which topics had been covered.

“Now, the first step to solving any problem is simply recognizing that there is one! Through a long conversation of objections and him trying to find a way out (full well knowing Ciara was of far greater value), he agreed. He made the joke he was only doing this because of my patience and understanding in reference to his rude comment when he was taking fire.

“By the end of the conversation (which turned more towards laughter), I was reminded once again that, in business, people want real conversations with people.

“Nobody wants to feel used for a commission. So many sales reps do not consider this and only look at the sale instead of the actual person and their needs.”

“His team implemented Ciara, are experiencing positive results, and are anxiously awaiting the release of our next version this Fall.”

Key takeaway: Don’t be afraid to be persistent. If you truly believe what you have to offer is of value, don’t give up.

Michael Heiberg

CEO of Ocean.io.

“Probably the most exhilarating sales experience I’ve had was being awarded a multimillion-dollar contract from the largest and most prestigious German tech company.

“SAP was the incumbent supplier and they used all the home-ground advantages you can imagine to prevent us from winning over the customer. All in vain: the better solution won the day.”

Key takeaway: Small ships can maneuver faster than large ones. Look for gaps in the incumbent competitor’s value proposition that you can fill.

Check out Ocean.io in the Pipedrive Marketplace.

Pedro Cortés

Founder of Cortés Design.

"I’m constantly reminded of (and surprised by) the power of a good offer—great solution, great positioning, great messaging—as it makes it 10 times easier to sell something.

“I remember spending a few months learning about my niche customer and their core problems. Once I started to spot the patterns it made everything easier.

“I now had the info to make my messaging and positioning spot on. I started getting more leads and people started saying things like:

  • ‘This is exactly what I need’
  • ‘I saw your website and had to book a call’
  • ‘I need someone that has your expertise’
  • ‘I’ve never seen an expert being this specific about what I need’
  • ‘When can we get started?’ (15 minutes after the call began)

“I honestly thought it wouldn’t work that well. But here’s the most memorable moment for me: I started closing $3k, $5k and even $10k projects with one call. No follow-ups, no proposals and barely any delay between jumping on a call and getting started. I thought that wasn’t possible.

“I thought I needed to explain myself more on the calls. I thought there was no way they could make a decision that fast because I used to take way longer to close a deal, my close rate was way lower and sales gurus seem to say that it’s all about the ‘follow-up.’

“That shifted my perspective completely and made me double down on my strengths (‘selling’ the visitors before they jump on a call, not during). That changed everything for my business, so I’ll never forget that.

“To be honest, I continue to underestimate how well a great offer can do 95% of the heavy lifting before people jump on a call. This still happens with both my business and with my SaaS clients.”

Key takeaway: Learn as much about your target audience as possible. Read industry studies to learn challenges, blog posts to understand pain points and reach out to your audience directly to figure out what their biggest challenges are.

Marek Beran

Head of Sales at CloudTalk.

“We have been working with a large BPO in the UK since the beginning of last year. It was developed from a cold call and it was a long journey to develop it into a real opportunity.

“After we successfully passed the free trial period and internal testing, we progressed to final proposal and getting the necessary global approvals. As it was the end of August, we were still on track to close the deal before the end of Q3. We prepared the deployment accordingly, including staffing and training on the client-side.

“Throughout September we were slowly finalizing the contract. Out of nowhere, some secondary security review became necessary (for those working with the Miller Heiman methodology, we forgot to map one technical buyer in procurement). This required results from some specific penetration test, which we obviously did not have.

“Two weeks to deployment, we were told either we provide the penetration test, or they will use our competitor. We all thought: ‘OK, this is game over. We cannot make this happen in two weeks when penetration tests normally last two months.’

“Luckily, the next day, we found a supplier that was willing to execute within our timeframe (for an extra high fee, of course). Working days and nights over those two weeks, on September 30th we received positive results from our penetration test and got the deal at the end of the day.

“The learning is: always map all your buying personas thoroughly!”

Key takeaway: As Marek says, “The learning is: always map all your buying personas thoroughly!” What are their internal buying processes? How can you make purchasing from you as easy as possible?

You can integrate CloudTalk with Pipedrive. Find out in the Pipedrive Marketplace.

Steven Lu

Founder of Interseller.

“The deal I love the most is when we signed with Greenhouse. We were initially just a partner with them, similar to how we are with Pipedrive.

“Eventually, we started helping the Greenhouse recruiting team to find talent and candidates. They actually made an offer to someone they found with Interseller within 14 days of using our product!”

Key takeaway: Work with everything you’ve got. Your partners are a potential source of leads, attention and sales opportunities just waiting to be tapped into.

Dipak Vadera

Sales Manager at Leadfeeder.

“I was speaking to a marketing decision maker at a startup after his team signed up to try Leadfeeder. He realized the immense value the platform could add to their daily activities, but he was straight up with me to let me know it wasn’t the right time.

“Not only was the company going through some structural changes, but their budgets were limited, and they didn’t have a big enough workforce to engage in outbound sales.

“I acknowledged that they weren’t ready to move forward yet, but sooner or later they would. It was just a question of ‘when’. Instead of burning that bridge, for the next couple of months, I kept in touch with my champion, sharing content, providing tips and advice from experience that could help him with other tasks and challenges he had on his plate.

“Lo and behold, 4 months later, I read up on how the company had secured $X million in funding and were now in the process of scaling their operations in EMEA. At the same time, I had a look at their careers page and noticed how they were now hiring for multiple salespeople.

“I dropped him a message and, within hours, got the green light from him to proceed with the purchase. It was the biggest deal we won that month!”

Key takeaway: Keep tabs on your prospects. Take action when something noteworthy happens within a target organization, whether that be new hires, funding or acquisitions.

Looking to generate more of your own quality leads so you can close more deals? Read the series on lead generation we created in partnership with Leadfeeder.

In the last article in our expert opinion series, you can find out what the experts think are the most valuable sales metrics to keep an eye on.

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