How to close a sale successfully

The first big win is a crucial moment in an entrepreneur's career. It's the deal that puts their little start-up on the podium with the best players, while infusing the team with new confidence and energy.

I remember Okta's first big win like it was yesterday. It was the opposite of smooth. I was traveling to Tulsa, Oklahoma, in the country, and on the way to the airport, I realized I had scheduled my flight for the bad day. I had to book a last-minute red eye to do it. After connecting in Chicago the next morning, I landed in Tulsa in the middle of a snowstorm, and had to walk along the side of a state highway from my hotel to the prospect's office to make the meeting. When I arrived, I was given a sports towel on the spot to dry off before getting started. Believe it or not, we're winning the business.

There's an expression in sales that applies perfectly here: "Earthquakes don't matter". As entrepreneurs, we often have to deal with circumstances beyond our control. At the end of the day, we have to succeed. For us, securing that good customer forced us to persevere and be flexible. This week in Zero at IPO, Epic Magazine's Joshua Davis and I talked to five entrepreneurs about the approaches that helped them win big. Here are the lessons they shared:

1. If someone says "no", find out why

Rejection is an integral part of the entrepreneurial spirit. Carl Eschenbach of Sequoia Capital, former president of VMware, recalled how VMware's first major victory began with a clear "no". After hours of negotiation, a multi-million dollar deal fell apart. But instead of leaving the prospect's boardroom, Eschenbach pressured the executive he was working with to stop them. In the end, once he and his team better understood the customer's point of view, they were able to reach an agreement.

2. Connect with everyone

Every entrepreneur needs to know how to connect with customers, investors and fellow founders. But these aren't the only people who can affect your career. Alex Asseily, co-founder of Jawbone, experienced this first-hand when he was about to sign his first big contract with AT&T. Production had been delayed several times, and by the time the shipment of Jawbone products arrived at the warehouse on the evening of the holiday delivery deadline, the facility was already closed for the weekend.

But then Asseily remembered a connection he'd made during a visit to the factory two months earlier in half the world: the warehouse owner. He reached out and was able to reopen the facility. Because Asseily forged relationships with all kinds of people, not just other tech executives, his vast network helped secure Jawbone's first big win.

3. Be transparent

Sometimes, good old-fashioned business practices will help you succeed. That's what Fred Luddy, founder of ServiceNow, learned from his first major deal.

In the early days of ServiceNow, Deutsche Bank expressed interest in what the company had to offer, but also asked for features that ServiceNow was not prepared to provide. Luddy considered accepting Deutsche Bank's initial proposal; after all, it would have meant a 50% increase in ServiceNow's revenues. Instead, he admitted that ServiceNow didn't have the capacity to offer all the functionality the company needed at the time. As a result, he developed an honest and open relationship with Deutsche Bank, which eventually turned into a relationship of trust with the customer.

4. Never let a key customer down

Maggie Wilderotter, former CEO of Frontier Communications, has always believed that every customer is a key account and should be treated as such. One of Frontier's big customers wasn't happy with her service, and although the organization isn't a brand, Wilderotter went the extra mile. She flew to Denver to meet key stakeholders face-to-face to discuss their concerns. And if that wasn't enough, he went on a road trip with the client to visit general managers in various locations where they were having problems with Frontier service. In the end, the customer appreciated his direct, hands-on service, and it ultimately became a long-standing win for the company.

5. Getting your hands dirty

Your competitors won't always play fair. Josh James, founder and CEO of Domo and co-founder and former CEO of Omniture, knows this from experience. Once, after Omniture had acquired another company (and a string of new customers), a competitor launched a targeted, negative advertising campaign to try and poach those new customers. The acquisition had been a big win for the company, and James didn't want to lose any ground. Omniture offered discounts to new customers. They also fought fire with fire, sending billboards to the competitor's parking lot, accompanied by people dressed in monkey suits handing out banana chips and recruiting the competitor's employees to "join the winner". For James, this strategy was successful, at least because he can now play "guerrilla marketing" puns whenever he tells the story.

While the big win is always important, entrepreneurs have different approaches to achieving it. However you get there, perseverance is the key. Remember: this moment sets the stage for what the company will become. Years after Okta's first big win (and my fateful trip to Oklahoma to close it), my main client contact called me from a new company to see if we could work together again. When I asked him why he'd come, he said, "I'll never forget seeing you walk into the conference room with a towel in your hand, drying your pants as you walked out into the field in that snowstorm."