5 Lessons from a Career in Sales

5 Lessons from a Career in Sales

A few weeks ago, our Chief Sales Officer, Justin Fite, sat down with the folks at SalesHacker for a webinar entitled, 3 Keys to Winning as a High-Growth Sales Org. In this session, Fite discusses some of the lessons, pitfalls, and key ideas he’s gleaned from over 20 years of sales experience. If you couldn’t be there, this blog series will catch you up. Here’s part one of three!

At each stage of his career, Lessonly’s Chief Sales Officer Justin Fite has learned important lessons that have shaped his sales leadership. He notes, “I’ve worked for some great organizations and learned from excellent people. I want to start off by taking a step back, giving you a sense of the experiences I’ve had, and what I’ve learned along the way.” With this backdrop, Fite highlights five lessons that have been absolutely critical to his career.
5 lessons career sales

Precision of work

Right out of school, Fite worked as a software engineer at McDonnell Douglas, now Boeing. When designing missile guidance systems, precision is essential. And Fite quickly learned the necessity of precision in an organization; but he also had a personal epiphany, “I learned a very important lesson there: the precision of work necessary to be an engineer was beyond my capacity. I just wasn’t that good at it.” This insight launched Fite’s ensuing sales career and provided a lesson that he draws upon regularly: knowing and understanding the personal limitations, of both himself and his team, is critical when building an organization—especially a high-growth sales team.

Clarification of value

Fite shifted to a role as a sales engineer at a startup. This job opened his eyes to the world of sales, and the importance of clearly communicating with customers. “It was my first exposure to a customer—focusing on and understanding clients is essential to satisfying their needs.”

Determining a buyer’s motivation is essential, so when a prospect asked a question, Fite learned not just to provide an answer, but to also consider the why behind their question.

This strategy helped him understand how doubt, fear, needs, and deeper interests drive a buyer, and clarify how his product addressed their needs.

Efficiency through process

As a young salesperson and sales manager at Rational Software, and later at IBM, Fite became convinced that efficiency in the sales process is critical. He experienced times of both slow and fast growth—along with the challenges of both extremes. As a result, Fite recommends a learner-first framework for developing learning processes and efficiencies. “We took a very pragmatic, simple approach, which was to ask, ‘What do our reps need?’ The reps and managers knew what that was, so they began to create materials. The most effective approach is to have involvement from the roles that really understand the function. That’s sales management.” With a democratized approach to developing best practices, Fite’s teams continued to grow and succeed.

Balancing funnel & focus

In sales management at companies like ExactTarget and Salesforce, Fite learned about balancing his team’s time with the various stages of the sales funnel—the hard way. He noted, “It’s very easy for reps and organizations to bounce between the top of the funnel and the bottom of the funnel. Many reps are over-focused on low-funnel activities, probably because as managers, we over-focus on that.” Fite recommends developing a steady cadence for every stage of the buyer journey.

Sales managers must excel at helping reps achieve this healthy balance, which in turn drives steady and repeatable sales.


Lately, Fite has served in leadership roles at multiple SaaS startups including Lessonly. With limited resources and astronomical goals, prioritization maximizes a sales team’s potential to improve and thrive. It’s essential to maximize the return on investment when hiring, purchasing sales tools, focusing on certain target markets, or allocating the time of employees. “As a leader, it’s critical to gauge problems accurately. We must determine the scope of fixing a problem against the value of getting a solution.  Essentially, is that worth fixing now or can it wait?”

These five lessons have been instrumental in Justin’s career, and inform his work every day as Lessonly’s CSO. In part two of this series, Fite will share the five greatest pitfalls of his 20+ years in sales. He’s lived out these shortcomings—and he’s sharing them so that other salespeople don’t have to. Check back next week to read on!

Lessonly helps sales teams learn lessons and close deals

These five ideas have informed Fite’s decision-making over 20 years of building sales organizations and mentoring sales professionals. His team uses Lessonly for modern sales training that helps them learn, practice, and perform in a high-growth, high-pressure industry. Want to see if Lessonly could be the perfect tool for your team? Take a tour.

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