Victory! Nothing beats the feeling of winning a huge deal.

After hours spent making calls, giving demos of your product, sending out emails, and making even more calls, you’ve finally crossed the finish line and closed a record-breaking deal. The best part of working in sales is celebrating your biggest wins as a reward for all of your hard work.

However, you should not only celebrate, but also reflect back on your biggest successes to find patterns and lessons you can learn from, especially when a deal is uncharted territory for your business. Rather than talking about general best practices and lessons you can learn from sales wins, we wanted to hear the real stories of sales wins in the field.

We asked sales reps and sales leaders to share some of their biggest ever sales wins with us, including details of the challenges they faced, the tactics they used, and the reasons they finally closed the deal. Hopefully, these trailblazing stories will give you valuable insights into the sales process that you can apply to your own sales team — and start winning more deals.

(Want to receive an alert as soon as someone on your sales team wins a deal? Check out our FREE mobile app: Champ!)


Going All In

James Pember is the CEO of Sparta Sales, but because the company is still an early-stage startup, he still holds quota and helps the sales team win deals. He explained that in the last 6 months, sales has been targeting the telecommunications businesses specifically.

“For a sales gamification company like us, telecommunications is an ideal customer,” he explained.

“They have a fast, transactional sales process and are normally staffed up with young millennials. Gamification works especially well in these environments where a lot of the sales success is based upon building an environment of fun, momentum, energy, transparency and recognition.”


He could see that we were never going to let the opportunity slip.

James Pember, CEO of Sparta Sales

However, selling software to telcos is a challenge, he noted. Often, these companies have home-built, on-premise solutions that are loosely tied together and really tricky to integrate with. On top of that, their complex organizational structures make it’s tough for sales reps to target the right department and find decision-makers.

Pember said in the end, it was their intense commitment to making the implementation a success that closed the deal.

“I remember at one point during one of the final meetings saying, ‘I can’t afford to not make this a success and I’ll work 24/7 to make sure that it is.’ In that moment, he was all in,” Pember explained. “He could see that we were never going to let the opportunity slip. Startups can use this tactic very, very effectively. As a young software company, you have a lot going against you. You probably lack features, credibility and a big support and implementation team. Using your commitment, enthusiasm and genuine excitement can really help get you over the line and cover up these gaps. ”

They were able to close the deal with the region’s biggest telco, Pember said. The company has 34 million customers in 10 countries throughout Europe, making it one of their biggest wins ever.

“This deal is absolutely one of the most critical in our company’s short history,” he said. “We overcame our toughest sales process to date, and came out the other side with a successful pilot integration, an internal champion and many more teams and departments to scale into.

Moving forward, we’ve realized that building strong relationships with our prospects, delivering value early in the sales process and making sure they know that we are 100% committed to success is the key to us closing bigger and better deals.”

Chasing Whales


Because I was new, I wasn’t afraid to go after bigger accounts.

Ben Solari, Account Executive at InsightSquared

Ben Solari had just been promoted from Business Development Rep to Account Executive at InsightSquared, and it was his very first month with a quota. He was in charge of building his own pipeline from scratch, and decided to chase some pretty big opportunities.

“I think it was a case of naiveté, but I was just trying to be aggressive as possible,” he explained. “I ended up having a few bigger companies come to the table — 5 to 6 times our average deal size if they decided to buy.”

He said he was a little over his head at first, navigating very complex deals. To make up for his inexperience, Solari relied on InsightSquared’s client services director to help answer technical questions, and the sales director to help negotiate the price when it came time to close the deal.

Even InsightSquared CEO, Fred Shilmover, was concerned that Solari was going to crash and burn.

“Fred came up to me to talk about all these big deals I was working,” he said. “He expressed some concern that I was wasting time with these companies because I hadn’t closed a single deal yet. He said, ‘Let’s focus on walking before we run.’ But I just used that as motivation.”

Solari said he really got lucky that this company was both ready and highly motivated to buy. He was able to push the deal across the finish line and exceed his quota by more than 400%.

“That deal came in, and it ended up being the 3rd largest deal in company history at that point,” Solari said. “A few takeaways for me were that 1. A sale never comes in a silo. It’s such a team effort, especially for a complex product like ours. I would not have been able to close the deal without the help of people here who don’t get to ring the gong when the deal closes. And 2. Because I was new, I wasn’t afraid to go after bigger accounts. Working for an analytics company, we use history to predict the future. That’s great from a macro sense, but you can’t let that prevent you from going after deals that historically might not have closed.”

Getting that First Deal

Ryan Gum is the CEO of Attach, and similar to Pember, is highly involved in the sales process because the company is an early-stage startup. He said one of the company’s biggest ever deals was their first completely unaffiliated customer, which is a huge deal in Software-as-a-Service.

“To ask someone who doesn’t know you to take a bet on a completely unproven product is a tough sell,” Gum said. “With no sales process in place, we started by sending out 10 personalized emails to target customers. Out of 10, 2 of them replied. One of them said ‘Sounds interesting, let’s talk in 6 months.’ 6 months? We hadn’t even been around 6 weeks! The other one ended up becoming our first client.”

He said it was a real struggle to close this deal, because the team was literally starting from nothing.


The deal we closed was small, but size was unimportant compared to what it meant.

Ryan Gum, CEO of Attach

There was no sales process, no track record, and no proof that their product offered real value to the market. All they had was a product that they believed would help salespeople, and they decided to use it strategically during the sales process.

“Attach gives salespeople a view into their buyers’ behavior and interests by telling them what happens to their sales decks after they hit send,” he explained. “So we were able to be a bit cheeky and ping prospects as soon as they had reviewed our deck. This let them know that it works, but more importantly, gave them a real life example of how they can use it to improve their own sales process.”

Gum said he believes this tactic helped the sales team make a real impact, stand out, and ultimately get prospects excited enough to take a risk on us and close the deal.

“When you’re a brand new startup and you take your MVP into the wild, that first deal means everything to you,” he said. “The deal we closed was small, but size was unimportant compared to what it meant — that we were building something that solved a pain point of a real company, with a product worth paying for.”

“If we can get one customer, we can probably get two. If we can get 2 we can get 10, and if we can get 10, we can get 100,” he explained. “It gave us the confidence that we were on the right track, which in a world of uncertainty that is an early-stage startup – that’s all you need to keep going.”

The Chess Game of Sales


When I finally got the VP on the phone, I had the sales operations team vouching for us.

Clark Bakstran, Account Executive at InsightSquared

Clark Bakstran is a Mid-Market Account Executive at InsightSquared and was responsible for closing one of the biggest upsells in the history of the company. He explained that the customer in question had five separate teams, and two of the teams had already bought InsightSquared.

“I was talking to one of the 3 teams we hadn’t sold to yet,” Bakstran said. “I had put my contact into trial and spent a while doing a lot of tech integration. He was my only contact for a while, and we were doing a lot of slow building to make sure he was comfortable with the product. It got to a point where I realized he wasn’t going to make any moves forward on his own and I had to figure out how to leverage other contacts in the company going forward.”

He decided to arrange a call with the sales managers and at the same time, got in touch with a sales operation employee who would be most affected by the new software.

“I got on a configuration call to talk about how to help her, but then also started talking about the other teams that were looking at using InsightSquared,” he explained. “We figured out our software would save her a ton of time personally. Then I learned that there was actually another person who built reports for the board, and I got in touch with her as well.”

Bakstran was able to give both sales ops employees a demo, getting both of them on board with buying the product. Then, when he reached the decision-making Sales VP, he had two solid sales champions on his side.

“When I finally got the VP on the phone, I had the sales operations team on the phone vouching for us,” Bakstran said. “It ended up being the two operations people and not the sales managers who really drove the deal forward.”

The VP was trying to get a discount as well, but the sales operation team was able to convince the VP that it was worth the price. Bakstran was able to close the deal — a huge upsell into a great company. He explained that he learned the importance of working the entire account, and getting lower-level employees on your side.

“When you’re working with a lot of people, you feel almost like you’re playing a chess game,” Bakstran said. “You have to make sure the right people talk to the right people at the right time.”

Hopefully you’ve enjoyed reading these sales win stories, and you also learned some valuable lessons for your own sales team.

What was your biggest ever sales win? Share it with us in the comments.

[contentblock id=160 img=gcb.png]
Recent Posts