Episode OneHundredTwentyFour

5 Things to Consider When Taking a Sales Job That Will Boost Your Career Long-Term

Guest: Dan O’Sullivan, VP of Sales, Travel Solutions, EMEA at TransPerfect

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About This Episode

When I was down at the Surf & Sales Summit, I met Dan O’Sullivan. We were hanging out down in Costa Rica together, surfing in the morning and talking sales in the afternoon. And when I heard a little about his story, I knew I had to invite him on the Sales Engagement podcast.

See, as a sales professional, he’s a bit of a unicorn. He’s been at one company, TransPerfect, for 22 years. Dan started as one of 7 salespeople and has risen to the role of VP of Sales, Travel Solutions, EMEA. So, I invited him on the show to talk about why staying at one company for a while can actually be really beneficial to your sales career. 

He had a lot of great wisdom to offer, so let’s dig in.

We’re seeing a rise in people bouncing from job to job…why is that?

Dan says there are a few reasons for this. 

For one, sales people get good at convincing companies that they’re good sales people, more than they actually get good at being good sales people. And it usually takes about two years for a company to wise up to that.

Second, it would seem that millennials have a desire to work at a lot of different companies and see a lot of different places. 

There’s also an allure to working at a company that’s going to grow rapidly, go public, and provide a huge payoff. And there’s a lot of incentive for those companies to perpetuate that dream. Because if they can convince you that maybe one day you’ll reap a great payout, then they can hire people less expensively or recruit people more easily. All with a very low risk attached.

Lastly, people have this tendency to, when they end up in an environment they don’t like, to just change out their environment. 

All of these things contribute to this phenomenon we’re seeing where young people change jobs every couple of years.

What advantages are there to staying at one company long-term?

There are a lot of benefits to staying at a company long-term. 

But here are two big ones.

When you think about he #1 driver of your success, and probably the #1 thing that makes you want to come into work every day, it’s your relationships.

But great relationships take time and challenge to get to. Every time you leave a company for a new one, you have to cut all of your current relationships and start new ones. 

By staying at one company, you’re giving relationships the time they need to develop well. And considering their link to success and motivation, you’re probably giving yourself a boost in those areas, too.

And here’s another thing. 

Sales is a job that has such a high ceiling for growth and learning. 

But if you’re switching jobs every couple of years, you’ll never get the chance to really dig deeper into issues like how to design solutions, how to land complex deals, or how to grow accounts over time. 

Those things take a long time to learn. And if you’re starting from scratch again and again, you’ll never really be able to move on to the next level.

So, how can sellers take a more long-term approach to their careers?

  1. Think about risk when evaluating a job. 

If you want to work at a startup or a company expected to go public, you need to bake that risk into your evaluation of the job. If you talk to most VCs, they’ll tell you that they expect about a 90% fail rate. They’ll invest in 10 companies to get 1 to pay off.

But if you’re working at one company, all your chips are on that company. 

So, if you are choosing between two companies, say a traditional firm where you know what you can make as a salesperson, and a startup, your payoff from the startup should be about 10 what you could make at the more traditional firm. 

  1. There’s not a magical environment will perfectly suit you. 

And even if you did find that magical environment, the nature of the world is that it changes so much, it probably won’t be like that for very long. 

So, the real trick in life is not, how to find an environment you like, but how to change the environment that you’re in to make it more like what you want. 

  1. Look at whether or not a company makes money today. 

Again, that’s especially true when we’re talking about the startup space. 

  1. Try to find a company that values sales, that is a sales-led organization. 

Look at a company’s compensation plan. Maybe it they have one that doesn’t reset every two years but instead allows you to take advantage of what you build over time. 

Look at the senior sales people in an organization. Have they been able to continue to build and grow and be compensated accordingly? Have they moved into a management role? 

If you don’t see people in the organization that have benefited over time, that’s a red flag. 

  1. Think about where you see the company going 20 years from now. 

When you look at the CEO or key executives, what do you think they’re really trying to do? Are they trying to build something that lasts? And do they have a plan that seems viable to actually do that? Or are they trying to build something that could be acquired by someone quickly?

So, when you’re thinking about your career, make sure you think through these five things to ensure you’re giving yourself the best chance at success and happiness.

This is an interview with Dan O’Sullivan from TransPerfect. To hear this episode, and many more like it, you can subscribe to The Sales Engagement Podcast on Apple Podcasts, on Spotify, or on our website.

About The Podcast

The Sales Engagement podcast is the #1 podcast focused on engaging your customers and prospects in the modern sales era. This show features real-life stories and best practices from revenue leaders doing the job day in and day out, in a casual, radio-like talk show.

Each episode features modern tactics, strategies, hacks, and tips to get the most out of your sales engagement strategy and help you navigate the next generation of sales. You’ll find energetic talks that will provide you with real actionable value around building meaningful connections and creating a better selling experience through authentic conversations that you can measure.

The Sales Engagement podcast is here to help B2B sales leaders, customer success leaders, and marketing leaders innovate and usher in the next era of modern sales by building pipeline, up-selling customers, and ultimately generating more revenue with more efficiency.

Hosted by Joe Vignolo, Senior Content Managing Editor at Outreach, and Mark Kosoglow, Vice President of Sales at Outreach.

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