To quit or not to quit, that is the question

Published: Wed, 08/02/23

August 2, 2023

TOGETHER WITH

Welcome to August, a fresh new month that brings with it endless opportunities to hound people into completing that Docusign before the impending end of summer fully crushes their spirit (it works). In this week’s issue, we interview a former engineer who made the transition into sales, share a Sales Fail about distrust, and give some advice to a rep looking to land an enterprise AE role.

NUMBER OF THE WEEK

5.3

The average new sales hire is fully productive in 5.3 months.

Source: Zippia

SALES ROUNDUP

Here’s what’s happening in the sales world this week:

Sales of Recreational Vehicles have cratered, especially when compared to the highs reached during the pandemic. According to Fortune, sales of RVs have tanked nearly 50 percent so far this year. In September 2021, RV sales were the highest on record, with over 55,000 sold. In June of this year, just 24,095 were sold. Experts say high rates and unprecedented pandemic-era sales are partly to blame. You can read more about it here.
WWE superstar Big Show opened up about his past, including his career as a car salesman before making it big in the weird world of wrestling. Big Show, whose real name is Paul Wight, was once a promising basketball player who dropped out of school before working a series of jobs, including stints as a bouncer, a bail bondsman, and yes, a used car salesman before getting a chance to wrestle from Hulk Hogan. You can read more about it here.

FEATURE

An interview with Brian Shimkus, a former engineer who made the transition into IT sales and hasn’t looked back

Brian Shimkus is an Account Executive at Dell. He is from Gilbert, Arizona, and has held various tech roles throughout a 20+ year career in Information Technology. We talked to Brian about his engineering background, how and why he chose to make the transition into sales, and what it’s like to work in IT tech sales in today’s ever-changing world.

You’ve been selling for over 10 years. How did you get your start in sales? When did you know it would be your career?

I started my sales journey as a presales engineer, supporting “Tier 1” customers including Commercial, State, Local, and K12 sectors. Having been a customer myself, I always appreciated working with sales teams who understood my industry, presented innovative solutions, and provided valuable insights. It was during a challenging project with a customer that I realized my passion was for showcasing how technology, combined with people and processes, could genuinely solve real-world problems and bring immense satisfaction.

You sell IT services and cloud infrastructure for Dell. But you also have an engineering background. Do you have to be technical (speak code) to sell IT/cloud solutions? If someone wanted to break into IT/cloud sales where should they start?

In the realm of technical sales, one must be adept at speaking multiple “languages.” Interacting with various stakeholders like application owners, infrastructure teams, and business process owners requires tailoring your communication to their specific needs. Some are deeply technical and seek configuration details, while others focus solely on business outcomes, emphasizing risk reduction, cost savings, and simplicity. While a technical background is beneficial, it's not an absolute requirement. Understanding business and corporate finance basics can also prove invaluable in comprehending how organizations function. For those pursuing technical sales, there are plenty of online courses available, such as those offered by CompTIA. Community college-level courses are also a great way to dive in without too much upfront investment.

You’ve been selling tech solutions nearly your entire career. How has tech sales changed since you started 10 years ago?

Over the past decade, I've witnessed a shift from point products to comprehensive solutions in the industry. Integrating multiple vendors can be overwhelming for organizations. Decision-makers are now more concerned with complete solutions and aligning technology purchases with their business goals. Working for a company with a diverse portfolio has transformed my approach to tech sales. Unlike earlier in my career, where we had limited offerings, my present organization covers multiple lines of business applicable to a wide range of customers. This shift requires a mindset focused on end-to-end solution selling and delivering direct business outcomes.

What does a typical work day look like for you? Walk us through it.

Each day in technical sales is unique but shares common themes: meeting with customers to understand their priorities and upcoming projects while exploring how our products/services can help achieve their goals. Internally, we engage in product updates, industry and technology trends discussions, account planning sessions, and more. Additionally, I actively participate in post-sales efforts, ensuring smooth transitions from the pre-sales phase to implementation teams. With an average of 10 to 15 customer-facing meetings per week, time management becomes crucial, especially when dealing with any unexpected customer satisfaction issues or “fire drills” that arise.

What's the one thing you’ve found that helps you be successful in sales?

Active listening and understanding the unique priorities and needs of different stakeholders is essential. Whether it's an Infrastructure Manager or someone from Procurement, comprehending what matters most to each stakeholder is key. Staying up-to-date with the latest industry trends and news is critical in remaining relevant to customers. Valuable information can be gleaned from various resources, including CIO-related newsletters, magazines, and industry-specific publications or user groups.

What are your long term career goals? Early retirement or future CRO

Making it to the end of the fiscal year 🙂

Joking aside, my long-term goal is to excel in the sales arena, supporting other sales teams with complex opportunities. Within our organization, the "Office of the CTO" provides internal enablement and customer-facing services. A role within that division would offer me the chance to enhance the skills of fellow sellers while continuing to engage with customers. Additionally, I find the blend of technical expertise, business outcomes, and customer feedback in Product/Program management intriguing and aspire to explore that avenue as well.

What is your favorite sales movie?

When it comes to sales movies, it's hard not to mention Glengarry Glen Ross, which depicts the highs and lows of the sales profession and the demanding expectations of zealous sales leaders. Another noteworthy film is Boiler Room, a masterclass in cold-calling and high-pressure sales tactics. On a more inspiring note, The Pursuit of Happyness is an uplifting story of overcoming challenges and achieving success in the sales world.

QWILR'S GUIDE TO HIGH-PERFORMING PROPOSALS

The quality of your proposal content matters. You only get one chance to make a first impression and in today’s competitive markets, it pays to be memorable. Our friends at Qwilr have put together this guide to high-performing proposals with real-life examples and best practices to engage buyers and progress deals.

Discover:

Creative ideas to impress and engage buyers
How to communicate the value of your solution
Content ideas that build trust and credibility
Best practices in virtual sales

Want to know how to make an impact? Download it for free today!

Get the Free Guide!

MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

The 2011 book, The ____ Sale became a highly-acclaimed bestseller.

A. Complex
B. Complimentary
C. Snuffleupagus
D. Challenger

SALES FAILS

Each week, we bring you the most cringe-worthy sales moments from across the web. To submit your sales fail story for consideration, click here. (Don't worry, you'll remain completely anonymous).

This happened to me at an old job but I'll never forget it. I was selling software to SMBs. I had spent three weeks working with a prospect who was finally ready to buy. He was really annoying throughout the entire process and kept saying he was looking for “a partner he could trust.” No matter how many times I tried to reassure him, he kept saying this.

Anyway, I finally emailed him the paperwork. It was the new standard template we had been using for the last few weeks. But it turns out that the page numbers at the bottom of the paperwork were wrong. The last page always said 'Page 8 of 9'. There was no page 9. I hadn't noticed it and no one else had said anything before.

As soon as I emailed him the paperwork, he emailed me back and asked where the 9th page was. I was surprised and apologized profusely, telling him that it was a mistake and that it was a new proposal template our company had just started using and that I would send him an updated document ASAP. He got all flustered and emailed me back saying that he doesn't do business with shady people. I never heard from him again; he completely ghosted me.

It was an honest mistake, but he really thought I was trying to pull something over on him. I talked to legal and got it fixed the next day. I still can't believe I lost a deal over something so silly, but now I ALWAYS check the page numbers on proposals before sending them out.

Anonymous Location Withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- July 2023

WORTH A PEEK

Ever heard of pattern interruption, the trick some marketers (and some sleazy influencers) use to capture your attention? Pattern interruption can work in sales too, and HubSpot has a solid article about how you can use it to get your prospect’s attention and get your message across. You can read the article here.

ASK THE QUOTA

Want to submit a question and be featured in our advice column? Click here. (Don't worry, you'll remain completely anonymous).

Dear Quota Team,

I've been working in sales since 2018, starting out as a commercial SDR in the tech space, and taking various roles with increased responsibility, and now find myself selling professional services at a software company.

I am responsible for the full sales cycle for multimillion dollar opportunities to enterprise level accounts, but my company considers my role sales support and therefore I do not have a variable component to my earnings, but software sellers that own the account get paid on it. I have a decent base salary, higher than the median mid-market AE, lower than an enterprise AE, and a metric driven bonus of 10%.

I'm tired of earning commissions for other people based off of my sales and want to pursue an enterprise AE role elsewhere (there are no open AE roles at my company). Based on my previous experience, I feel that I am going to have a hard time getting an enterprise role because I don't have software specific closing experience.

How can I improve my odds of securing an AE role that will pay me what I deserve?

Underpaid in the Southeast

Dear Underpaid,

This question was a bit above our pay grade (see what we did there?) so we reached out to Ryan Walsh, CEO of RepVue, a sales organization ratings and transparency platform, to get his take.

If you’re looking to make the switch into becoming an enterprise AE, here are some things you should highlight about yourself when you apply:

The size of the accounts you've been working
The size of the transactions you've been closing
The fact that you have full-cycle visibility
That you’re selling within a software org and understand the process in great detail
The reason you're looking is to increase your upside and round out your experience

But Ryan also cautions about your timing. He says, “Those are all ways to 'sell yourself', but also note that it's still very much a bear market for many roles and orgs in software sales, so consider the following:

Wait it out a bit, be successful, show a nice long tenure on your resume, and early next year, we feel the market will be in much better shape and your resume will be stronger too.
The hard truth is that you may need to take a slight step back in base and maybe take on a mid-market role first so you can make that transition into selling software. But if you do that successfully, enterprise roles will be available sooner than you'd think.”

We hope this helps. Good luck!