Episode TwoHundredSixtyOne

Land Your Dream Job in Tech Sales

Guest: Stephen Farnsworth, Head of Product Marketing, Revenue Operations at Workato

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About This Episode

Most of us in sales didn’t wake up one day with a calling (although the ones who did are a force of nature, too).

We discovered it accidentally… or because it was the first job we could get… or by word of mouth… or because we read something about how great it was.

Recently on Sales Engagement, we featured the stories of three onetime SDRs who talk about how they discovered their dream job:

Let’s hear how these amazing salespeople made it into tech sales!

Stephen’s Story

Stephen started out working on corporate strategy at a sleepy insurance company. He was making money, he had a lot of executive visibility, he worked on high priority projects… but there wasn’t much mobility.

When Stephen realized that, he started to look into tech sales. “You get into tech by being technical or non technical. I wasn’t very technical. So if I’m non technical, the route that is seemingly the most natural to go into is SDR,” he said.

It was a hit to his ego, he confessed, to become an entry level SDR after his success at his other position.

“The positive of being an SDR is you can create your own luck and create your own success,” Stephen said.

It clicked that Stephen had complete control over himself — and could outwork anybody.

To SDRs who are just out of college without the benefit of his prior work experience, this is Stephen’s advice: “Put yourself in those shoes of who you’re selling to for a period of time. …Being able to have an intelligent conversation with someone is really important.”

To hear more of Stephen’s story, including his journey from SDR to marketing leadership, listen to the whole episode.

Roberto’s Story

Roberto is an AE at Outreach. Before that, he was an AE at two other companies. 

Before that… he googled “What’s the highest paying sales job?” — and that’s how he got into software sales.

“I made as much money in six months as an SDR that I did an entire year in a non tech role as an AE,” Roberto said.

Some things he loves about tech sales: The companies have fantastic culture, there’s always going to be something new around the corner, and the opportunities for growth are staggering.

One thing Roberto noticed after breaking into tech sales was that it was, you know, kind of hard. “Your rate of rejection is increased exponentially as an SDR. That’s not something that you can get used to until you actually do it,” he said.

The first couple of quarters are mentally rough, but after that you’ll see the personal and professional growth that can help you survive.

To SDRs who want to become AEs, this is Roberto’s advice: “Create the path yourself. If you’re an SDR that wants to be an AE, you’ve got to start thinking like an AE right now,” he said.

To hear about Roberto’s transition from SDR to AE, listen to the whole episode.

Meghan’s Story

Meghan was in retail sales and already passionate about selling when she decided she’d rather work for a startup than a big name brand.

“The ability for career advancement and operating more in the sense of a family than a large business lined up with my own goals and values,” she said.

The SDR role gave Meghan the basic knowledge to understand SaaS B2B sales and get her feet wet. “I’m a SaaSer for life. I’m never going back. Definitely found my passion,” Meghan said.

One thing that differed from Meghan’s previous sales roles was that in SaaS sales, everyone belonged to a team, the SDRs learned together, and they failed and won together. Not that it wasn’t challenging, but there was a camaraderie she hadn’t expected.

To a brand new SDR, this is Meghan’s advice: “It’s okay to ask for advice. If you realize you’re not as strong on the phone as you are on emails, you just have to align yourself with those people who are successful or that are willing to help and coach you,” she said. “The more you ask, the harder it is for you to fail.”

To hear more about Meghan’s current role as sales sequence specialist, listen to the whole episode.

Special thanks to our three guests! Get in touch with Stephen, Roberto, and Meghan at LinkedIn.

P.S. Outreach is hiring SDRs!

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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