From sales rep to CEO

Published: Wed, 09/04/24

Updated: Wed, 09/04/24

September 4, 2024

TOGETHER WITH

Welcome back to The Quota, the sales newsletter that ages like fine wine (as long as you store it in a climate-controlled email browser). In this week’s issue, our friends at Clearitty will give you the opportunity to earn a $25 Amazon gift card simply by filling out a short survey. Otherwise, enjoy our regularly scheduled programming, including an interview with a sales rep-turned-CEO!

NUMBER OF THE WEEK

37% of sales representatives produce the most leads from phone calls during cold outreach

Source: HubSpot

SALES ROUNDUP

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

Google representatives allegedly gave ad buyers tips on how they could reach teens, even though the company bars targeted advertisements to users under the age of 18. The reported behavior could potentially raise concerns under the Children’s Online Privacy Protection Act (COPPA), which prohibits platforms from collecting personal information on kids under 13 without parental consent. You can read more about it here.
A salesman for a moving company that held customer goods hostage has been sentenced to two years in prison as part of a crackdown on moving company fraud in New York City. The salesman, Andre Prince, was convicted of conspiracy to commit wire fraud, and used fake names while working for companies that also frequently swapped identities. You can read more about the scheme here.

FEATURE

An interview with Mike Glaicar, former salesman turned media company CEO

Mike Glaicar currently serves as CEO of media company NewBeauty. Prior to becoming CEO, Mike led NewBeauty’s sales team as Chief Revenue Officer. Mike has sold digital and print media for over 10 years and founded his own sales technology company. He lives in New Jersey with his wife and three children.

(note: this interview has been edited for length. You can read the full interview here).

You’re in the boardroom now, but you started your career off in sales. How did you get your start?

My first sales job was at a company called MJH Life Sciences. At the time, they were out of a small office building in Plainsboro, New Jersey. I was selling ads to large pharma companies for a magazine called Pharmacy Times. It was kind of a trial by fire situation. They threw me right into the mix and I learned how to sell print and digital media pretty quickly.

After about a year and a half, I had the opportunity to move into sales management. I realized very quickly how much sales skills translate to management skills. In many ways, it’s just understanding people and what makes people motivated, whether that’s buying from you as a seller or working for you as a manager.

I was in management for about a year and a half before I was approached by someone at Fast Company magazine to run their finance and pharma verticals. So I went over there and sold for them for about a year and a half.

How did you work your way up to CEO? What was the trajectory?

After working at Fast Company and seeing our editors write about the most amazing startups in the world, I got the entrepreneurial itch and decided to start a company: a tech startup in the sales engagement space. I was a solo founder with a small team of developers. I worked on that company for a few years. The tech startup space isn’t easy.

One day, I was pitching our software to a CEO who was a potential client. After a 30-minute meeting, he said, why don't you come and consult for a little bit? We're not ready for the software, but come consult and help my team out.

At the time, I hadn't paid myself for a couple of years. I was investing everything back into the business, so I decided to jump on the consulting gig. After a few months, he came to me and asked if I would join the team full time. I ended up joining Sandow as EVP of Sales and Marketing.

It was funny because I said two things to myself when I started my company. I said I'd never go back to working in media and I'd never work in New York City again because the commute from New Jersey was so brutal. I ended up doing both. But the only reason I did it was because I really liked their approach on how they ran a media company. That and the brand I was working on within Sandow, NewBeauty, had very strong engagement with their audience. So I thought we could create some platforms and sell things outside of traditional media based off of the data that we were capturing from our readers. Very quickly after joining the team, we did a full corporate restructuring and I took over the Chief Revenue Office role.

At the time when I joined, our sales team was not huge. We had a regional and national sales team which equated to about twelve reps overall when I joined. It wasn't that different from the management that I had done previously.

I was CRO for two years, I had sort of taken over a bit of an operational role of the business as well. I was working on some new initiatives for our brand and ad offerings, then at the beginning of this year, moved into the CEO role, overseeing the business overall. I think being CEO has taught me more than ever the importance of finding, attracting and keeping that top talent.

What’s one piece of advice you have for salespeople reading this who want the top job (CEO) some day?

I think a great skill is learning how to manage up. So if you're a salesperson and you don't manage anyone, learn how to manage your manager's expectations.

Be super communicative as far as letting them know what's going on with your accounts and what they should expect. Always look for ways to create solutions for your manager. Never go to your manager with just a problem, come with solutions too. When you're eventually a manager, you better be able to create those solutions on the spot. You’ll be honing your skills for what you need to do as a manager or as a leader in an organization.

What’s your favorite sales movie?

Although it doesn’t seem like a sales movie, The Big Short is an amazing example of people trying to sell an idea to people who don’t believe it — great lessons from that movie.

Get real-life insights from reps who have sold to your target accounts

First, our friends at Clearitty are offering The Quota readers a $25 Amazon gift card! All you have to do is share a deal success story — you can take the short survey here (create a free account to take the survey).

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MEME OF THE WEEK

Source: Instagram -- Sales Humor

Cox Media is hiring sales leaders

Are you a sales leader looking for your next role? Our friends at Cox Media are hiring for Director-level sales roles in Florida and Louisiana, with OTE of over $220K.

Cox offers:

Competitive salary plus bonus & incentive plans
Top-notch benefits (including health coverage from day one)
Rewards and Recognition (and incentive trips!)
Work-life balance and flexibility

Looking for a different role? Cox is hiring remote and in-person roles for their sales team across the country. Browse all open roles here to join the Cox family.

Apply today!

QUIZ

Daniel Pink’s 2013 best-selling book is called To Sell is _____.

A. Honest
B. Wonderful
C. Stupid
D. Human

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 is a story that happened to me earlier in my career but actually taught me a valuable lesson about being thorough before sending out emails. I was selling marketing services for a small company. Our sales team was about 15 people total. It was a very "sales bro" environment, but it was fun.

Our company ended up buying these expensive contact lists for us to do mass cold email outreach. I got my list, which was 1,000 emails. I went ahead and wrote out my pitch for the email sequence and built out the campaign in our software. It was some really crappy outreach software that was hard to use and I never really got the hang of. Well, I messed up the [First_Name] dynamic template and ended up sending out the emails to the entire list with the 'Hey John' placeholder to every prospect. I didn't want to tell my manager, but I told one of my coworkers about the screw up over beers that evening.

My coworker ended up telling the entire team and people kept saying, "Hey John,' to me every time they saw me the next few days. We had our standard end-of-the-week all hands sales meeting, and at the end of the meeting, my sales manager put my email up on the screen of the conference room for everyone else to laugh at as a lesson for why everyone needed to double check emails before hitting send. The sales manager called me up and presented me with a custom t-shirt they had made that said "Hey John" on it. Everyone in the room started laughing as they made me put the shirt on as punishment and wear it for the rest of the day. Eventually, the "Hey John" stopped and I ended up staying at the company for two more years. But I triple check every email I send now.

Anonymous Location withheld

GRAPH OF THE WEEK

Source: LinkedIn Poll -- August 2024

WORTH A PEEK

What do CEOs from top companies look for when hiring salespeople? Inc.'s annual CEO Survey found that 45 percent of CEOs of Inc. 5000 companies believe cultural fit to be the most important characteristic in a salesperson. You can read the rest of the list 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 am 24 years old and two years out of college. My first job after graduation was a customer support role with my current company. I didn’t mind the job but the pay wasn’t great and there was really not a whole lot of room for advancement. Knowing this, I decided to switch over to sales, still with the same company.

I have been in sales for almost six months now. The first few months, I was in training and had ramp pay. But I have been off ramp for close to four months now and things are going pretty badly. I can close deals but the number of leads I have to go through to get there is very high. My company tracks everything, and I am already on something like a PIP (it’s not called that) which means they’re limiting how many inbound leads I can take, given my lower closing percentage.

Besides that, I have realized that I might hate this job. I’m not motivated to convince customers of anything, even though it means more money for me. I don’t like the “chase,” and I miss the days when I could just sit back and answer calls and help people solve problems without having a huge quota looming over me. Is this a sign that I should quit sales? I am starting to dread waking up in the morning.

Miserable in Location Withheld

Dear Miserable,

Normally, we might attribute your troubles to growing pains, but (using your own words) dreading waking up in the morning and hating your job are pretty good indicators that you’re not in the right place. Could you stick it out for another six months, just to say you gave it a fair shot? If so, do it and see what happens. If the answer is a hard no, then do yourself (and your company) a favor and ask to be transferred back to customer support. There’s no shame in doing what’s best for everyone. Good luck!

Quiz Answer: D. Daniel Pink’s 2013 best-selling book is called To Sell is Human (you can read the source article here)

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Today's email was written by Ken Kupchik, Erica Furgiuele, Steve Rado, and Emily Hill.

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