In the engineer-glorifying culture of Silicon Valley, salespeople are often an overlooked breed.
But there’s a man who’s quietly built his legacy by mastering the art of selling business software.
Meet Dave Rudnitsky, senior VP of enterprise sales at Insidesales.com, a software startup that was last valued at roughly $1.5 billion.
Although he started in finance, Rudnitsky soon made the jump to sales and carved out an incredible 30-year career, helping grow some of the most groundbreaking tech companies, including Oracle, Netscape, and Salesforce early on — even earning a separate chapter about his prolific sales skills in Salesforce CEO Marc Benioff’s 2009 book, “Behind the Cloud.”
“If you’re going to build the greatest product in the world, you’re going to need the greatest engineers in the world. But if you can’t execute on it, you’re going to fail,” Rudnitsky tells Business Insider. “And executing means selling.”
Finance to sales
Rudnitsky first got into sales for a simple reason: money.
In his first job out of college, with payroll software company ADP’s finance team, Rudnitsky realised his peers in sales were getting paid a lot more than he was.
“At a minimum 3 times more,” he recalls.
For someone who wanted to help his immigrant parents enjoy a better life, a bigger paycheck was important, Rudnitsky says.
So at 23 years old, without any prior sales experience, he started knocking on the door of ADP’s VP of sales office every morning, asking to become part of the sales team.
The sales chief wasn’t convinced at first but he liked Rudnitsky’s drive. So he tested Rudnitsky by asking him to sell an ancillary product to ADP’s main payroll software. Rudnitsky totally killed it, outselling most of the sales reps, and winning the approval to join the sales team full time.
Once on the sales team, Rudnitsky was on a roll. His first sales manager Bob Schiff says he remembers Rudnitsky showing up with multiple new contracts every week, outpacing other reps, and winning the company’s annual President’s Club award every year, which is only given to the top salespeople at ADP.
“I can still picture him coming into my office, sales orders signed,” Schiff tells us about Rudnitsky’s early days at ADP.
Money wasn’t the only thing Rudnitsky started to like about sales. He also preferred the unpredictable, and almost chaotic, nature of sales over the more standard 9-to-5 worklife of a finance person.
“I didn’t want to be that guy in the same parking space every day, same cubicle, who goes home at 5PM. That’s not me,” Rudnitsky says. “If you enjoy chaos, get into sales.”
Oracle, Netscape, and Salesforce
Rudnitsky not only stands out for his sales chops. He also has a knack for spotting the next rocketship startup before it becomes a multi-billion dollar company.
After five years at ADP, Rudnitsky spent some time at a company called Pansophic Systems, which was later acquired by CA Technologies.
Next, he joined Oracle four years after it went public, helping it grow. Five years later, he was recruited by Netscape as its sales VP, where he worked closely with Jim Barksdale, Todd Rulon-Miller, and Marc Andreessen. Rudnitsky got Netscape’s first enterprise deal when he sold 10,000 browsers to McGraw-Hill.
Then he worked at Ariba, which was eventually acquired by SAP for $4.3 billion, before joining Salesforce in its early days, where he ended up spending 12 years. He also sold Salesforce’s first thousand-seat, enterprise deal to a company called SunGard.
Now he’s at Insidesales.com, another hotshot startup that’s raised over $200 million over the past 4 years.
“David’s genius for selling to enterprise clients was matched only by his gift for picking game-changing startup companies,” Benioff writes in his book.
Secret sales playbook
Rudnitsky says there’s no secret shortcut to selling more. You simply have to be hungry and relentless, and ready to out hustle your competitors.
On top of that, you have to be competitive, with that sense of hating to lose.
“The best salespeople I know, they’re more motivated by losing than they are by winning. You have to have this idea that you almost fear failure more than you enjoy success,” he says.
And as you start to gain more experience and go through more sales cycles, Rudnitsky says the “ball starts to look a lot bigger,” making it easy to hit it out of the park.
“It’s about repetition. You either sink or swim, right? And I’m swimming,” he says.
But even with all the right qualities, Rudnitsky points out, you could fail if you ignore the most basic part about sales: having a plan.
It’s why he came up with “The Rudnitsky Sales Playbook,” which Benioff featured in his book. As Benioff put it, Rudnitsky’s sales playbook was initially designed for his own team, but was later shared companywide as it had some of the most important lessons any salesperson could learn.
Here are the 11 rules from “The Rudnitsky Sales Playbook”:
1. “Think BIG, Have Attitude”: Think big (dollars and scope), not just the immediate opportunity in front of you.
2. “No deal is won or lost alone”: Work with the entire team to close deals.
3. “Connect the dots”: Never cold-call — always call with a plan.
4. “Focus on ‘why not'”: Instead of thinking about why a deal will close, focus on why it might not.
5. “Always take the deal off the table”: Make sure every deal is closed if it’s ready to close.
6. “Get your face in the place”: Meet your customers in person.
7. “Fun facts build instant credibility”: Try to learn everything about your customer.
8. “Be proactive on all paperwork”: Make sure all paperwork is in place.
9. “Always get quid pro quo in negotiations”: Don’t be afraid to ask for more and say no when needed.
10. “Share best practices”: Share them with the team and try to learn from them.
11. “Go after game changers”: Look for deals that can take the company to the next level.
“The greatest players think 3-4 steps ahead. You have to have a plan. That to me is a sign that somebody’s going to be successful,” Rudnitsky says.
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