AI or Bots Won’t Make You $200,000+ in Your Next Sales Job

Picture yourself as a hotshot Account Executive with three years of selling experience in your first sales job.

You are selling data-driven marketing software as a service (SaaS) to businesses.  You earn a $70,000 base salary and made about $160,000 all in this past year. Not too shabby for 3 years of sales experience (mom was so proud over the holidays). Your Average Order Value (AOV) is $18,000. Sales Cycle, only 38 days.  You hit over 125% of your goal the last two years since you graduated from the Sales Development Rep (SDR) program.  You doubled down early on and took a “blue-collar” approach by applying a tireless work ethic to prospecting.  You still use the skills you learned early on and continue to grind.  You cold prospect systematically, network, you are a leader, are creative – whatever it takes.  Your sales career is off to a fast start!

Now – Fast Forward to 2020. 

Trump is campaigning (and still tweeting…) for a second term, wow did that go fast! Life is good because you leveraged your sales metrics via Upsider to finally landed your first true Enterprise Sales Director role at a big time company. You start right away, congrats! You are excited. Big time deal sizes, challenging sales cycles, C-level decision makers, a legit expense account. Onward and upward, baby!

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Your First day

After a 17 minute Hyperloop from 217 miles away, you walk in the door to your new office on your first day feeling confident, if not a little cocky.  Your awesome new company has a powerful brand, hot product and has invested heavily in the latest and greatest in sales development and inbound marketing.  First up? Sales team orientation. You put on your standard issue Virtual Reality (VR) headset for the new hire presentation and pass out some virtual fist bumps to your new teammates in other locations.  You are all sitting in a virtual tent at a virtual base camp on virtual Mount Everest. Nice touch, inspiring!

You first learn more about your new “Sherpas” as the company has enlisted a large group of excitable SDR’s. Most of them recently went through a 12 week, online, immersive sales boot camp (2020’s version of college). Despite their lack of excessive college loans, they somehow are still super hungry and ready to rock the phones (yes, cold calls are still a thing). They also are going to be deploying dynamic, customized and contextually relevant cold emails (yup, those still exist too).   They are even sending the newest version of MicroLinkedInSoft InMail, in 2020 everyone is connected (seriously. everyone).

Finally, you get to the part about the new Sales Development Operation Innovations team you heard so much about and it’s just as advertised. It’s like having 6 automated Alfred’s working non-stop in your Batcave! This company has built a Sales Development mad-scientist laboratory and are deploying the latest and greatest AI driven technology. Automated email that uses AI and predictive analytics to identify hot buyer prospecting and to predict sales cycles, sassy chatbots, same day drone schwag delivery, advanced marketing automation, VR webinars (Vrebinars? Ugh.) – you name it!

You have got it made in the shade. You now have an army to score you demos to pitch your AI-driven SaaS solution to CMO’s! Booya! Now you can just kick back, relax and let the leads FLOW, you are ready to drop some virtual demo’s like they’re hot (disclaimer: no one says that anymore in 2020… just like 2017). You paid your dues so you can relax a bit.  No more grinding, no more early mornings or late nights trying to find that last lead to put you over your quarterly goal, no more prospecting, right? Not so fast…

The Future is Now and $200,000 Requires Prospecting

It’s always fun to think about the future, but it can be dangerous too. Who knows whether the things in this grossly exaggerated, hypothetical future come true or not. The fact of the matter is right now a  sales job that will pay $200k+ OTE in 2017 more than likely requires you to prospect, build relationships and be creative and influential in doing so.

We’re just about a year old here at Upsider, and have upwards of 50 dynamic and fasting growing NYC SaaS, MarketingTech and AdTech employers on our platform hiring salespeople. We are a personalized data company for salespeople and sales teams with a jobs marketplace component. We hear a lot of conversation about AI, Bots, etc… augmenting and/or replacing salespeople and everyone seems to have an opinion. This got us thinking, where do we stand in 2017, when it comes to prospecting? So we did what we tend to do over here and decided to dig into the data. What we learned was that if you want to make well over $200k consistently for the life of your career, you simply are going have to prospect for your own leads.  Yes – even at really great companies, with hot products.

In fact, 80% of the opportunities on our platform that offer $200,000 OTE or more, require you to generate at least 50% of your own leads.  This data, our employer partners, the market, the ever increasing competitive landscape – it’s all telling us that your current relationships, inbound marketing, an SDR program, chatbots, drones, VRebinars (yes, unfortunately, they already exist!), whatever you have currently at your disposal; is not enough to keep your sales career moving forward at an accelerated pace. Let me be clear: it’s not your VP of Sales, your CEO… or some talking head Co-founder at a startup (ahem), it’s the data that says you should always be prospecting.

Wait There’s More… Data? Do tell!

% of Leads Self-Generated is just one of the unique data points we collect at Upsider, as we are doubling down to make real sales data the first priority, before resumes and job descriptions. This allows us to stay in front of what is trending and provide insight into not only what the best opportunities are, but what they require.

If you are in the New York City area and would like to better understand your sales metrics and see how they stack up versus high growth, upside opportunities and other top sales reps (anonymously), spend the 2 minutes it takes and register for Upsider. Regardless of what an uncertain future holds, tracking and organizing your personal sales data and seeing the opportunities in front of you in real time will help you make the best career decisions at the right times moving forward.



Drew Koloski is a Co-founder at Upsider and proud father to three little Upsiders.

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