What happens when you lose your dream sales job?

Published: Wed, 12/07/22

December 7, 2022

TOGETHER WITH

Welcome back. Let’s make one thing clear: we’re not here to remind you that there are only three selling weeks left in the year; we’re here to distract you from that fact for about ten minutes. In this week’s issue, we interview the first (sales) employee at Outreach, share a Sales Fail about boundaries, and give some advice to a rep who regrets quitting their dream job. Let’s do this.

NUMBER OF THE WEEK

25% of data in a typical sales database is inaccurate.

Source: Internal Results

SALES ROUNDUP

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

Even the world heavyweight champion Tyson Fury is interested in getting into sales, recently revealing that he’d consider becoming a car salesman (again) after his eventual retirement from boxing. “Maybe I’ll go back to being a used car salesman and open myself a little pitch in Morecambe somewhere,” the champ said in an interview with The Sportsman. You can read more about it here.
In perhaps the most explosive case of quiet quitting yet, Salesforce co-CEO Bret Taylor has announced that he will be leaving the tech giant by the end of January 2023. The news sent Salesforce stock tumbling, and has raised questions about whether there’s more to the story than is being publicly revealed. You can read a quick report here.

FEATURE

Mark Kosoglow

An interview with Mark Kosoglow, Chief Revenue Officer at Catalyst and the first employee at Outreach

What’s it like to be the first sales employee at a fledgling startup? We wanted to find out, so we reached out to Mark Kosoglow, who was the first employee at Outreach before the company was a household name. He worked his way up to Senior Vice President of Global Sales as the company grew, and is now the Chief Revenue Officer for Catalyst Software. Mark was kind enough to sit down for an interview and tell us about his journey. (note: this interview has been edited for length and clarity, you can read the full interview here).

1. First off, how did you get your start in sales? When did you know that it would be your career?

My real sales career began when I was a teenager. My dad told me I had to get a job. He told me to find a job I wanted, or else he would take me to the grocery store the day after my birthday and I’d work there. So I relentlessly called a shoe store at our local mall, and eventually wore down the manager enough that she gave me an interview. I ended up getting the job.

When I went to college, I did a couple of telemarketing jobs. Later, I actually got a job at the same shoe store (it was a seven store chain in Mississippi). So I continued to sell shoes. I was the top salesperson out of all seven stores in Mississippi, even though I worked half as many hours as some of the employees. I was just unbelievably good at selling shoes. That's when I knew I was good at sales. Every sales job I did really well, so I decided it would be my career.

2. You were the first employee at Outreach. What was it like running a sales team at a fast-paced startup?

It was no different than any other job I'd had. It wasn't easier or harder. It was just different.

You know, the story goes that Manny Medina (the Outreach CEO) was my first SDR. That's completely true. He gave me about a thousand leads a week. I took those leads and put them into Outreach’s first product, which was a sequencing product that automates multiple touches over time. If they replied, we would book a meeting. And with thousands of people in the sequence, I had my weeks filled with meeting upon meeting.

I would run all of those meetings every day, and we did about a million dollars in sales in the first six months. Then I hired a sales team. I still did some of the sales, but I hired three people that I knew well and one person that was referred to me by someone I trusted. The person who was referred to me ended up being the top rep at Outreach. I think he is still one of the top reps, and probably sold more Outreach than anybody in history if you add all the sales together.

3. What are some things you did to win deals over your competitors?

We had some built-in product differentiators, and we identified what those were, and we sold their value, and we reordered buying criteria to make those super important. For example, we were the only company that had an unsubscribe link in our sequences, and we sold that to our customers in a way like, “you're gonna endanger your company if you don't have this.”

We would regularly release some innovation that would again create a huge gap in differentiation, and we would win at a higher rate and at a higher price point. We probably went through five or six iterations of that over eight years.

4. At Outreach, you were selling sales-tech to sales teams, how is selling to salespeople different from selling to non-salespeople. Is it easier or harder?

Salespeople think they know all your tricks. But they really don't. The things that you do, you know, the sales techniques that you use in order to help people make a good decision. You would think that they would realize what you were doing, but they don't.

The second thing is, you'd expect they would respect call calling? They don't. I can't tell you how many times people have reamed out one of my SDRs for calling, when I know that their sales team is doing the exact same thing at the exact same time.

That was the most surprising thing to me. I thought that game would recognize game. Like really appreciating a great discovery call for example. Some people did realize that they were in a great sales process, and we did get complimented on that all the time. But I would have thought that it would have made a bigger difference than it did.

5. What's your favorite sales movie?

There's a bunch of cliche ones, but I think they're all very wrong, in terms of culture, mentality, you know. I think that they actually hurt the sales profession rather than help it. I don't know if typical sales movies give you the right energy to be in the right mindset to help your customer. So I might argue there's not a good sales movie out there.

AN UNFAIR ADVANTAGE FOR SALES REPS

Salesroom was developed specifically for remote-driven sales environments. Help your sales teams stand out and cut through the noise with a video conferencing platform designed specifically for sales teams!

Salesroom includes:

AI coaching (seamless meeting framework, airtime analysis, question detection, and real-time next step detection)
Sharable video highlights and recaps
Real-time insights (including the percentage of time you’ve been talking vs. the prospect)
Airtime analysis (ML engine will learn your behavior and communication style over time/meetings and suggest improvements)
Live transcription
Suggestions based on your preferred framework (MEDDIC, BANT, etc.)
And much, much more!

Get Started with a smart, insights-driven meeting platform that gives sales reps an unfair advantage.

Try Salesroom for free here!

MEME OF THE WEEK

Source: Instagram -- Sales Humor

QUIZ

What does the acronym MEDDIC stand for?

A. Metrics, Economic Pain, Determining Criteria, Decision, Identity, Closing Process
B. Metrics, Economic Buyer, Decision Criteria, Decision Process, Identify Pain, Champion
C. Money, Education, Decision, Diversion, Interest, Closing
D. Metrics, Education, Determining Criteria, Decision Process, Intelligence, Closing Criteria

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 this past year, and I’m still not over it. I sell telecom to small businesses for a regional company. I’ve been doing this for almost eight years and am pretty darn good at it. So when I got an inbound lead from a prospect who was opening his second and third restaurants, I was confident it would be an easy deal to close. Oh, and I'm a woman, since it’s clearly relevant to this story.

We went over options and he was nice and asked a lot of questions, then he started asking about my personal life, which is fine, I can talk to anybody and it’s usually a great way to build rapport with someone. But then he said he would only be able to look at the contract over the weekend, and asked if I could go over it with him then. I said I didn’t work weekends, and our office was literally closed, so he asked if I could do it from home.

He didn’t make me feel uncomfortable or anything, so I thought ok, no big deal, and agreed to call him that Saturday. Well, the mistake I made was to call without blocking out my cell phone number. That day, all he wanted to do was have a personal conversation and he kept asking me questions about who I lived with and whether or not I was single. After a while, I had to get curt with him to keep him on track. In the end, he signed.

Well, after that, he called and texted me almost thirty times in a three day period. After I tried to keep it professional for the first few messages, he basically ignored me and kept trying to have a conversation, even when I ignored him. In the end, I put together a message explaining that this was just a business transaction, and that if he had any questions to email my sales manager and that I wouldn’t be responding or accepting any more of his calls. That finally got the point across. Let this be a lesson to all sales reps (especially women) – NEVER give out your personal phone number if there’s a better alternative.

Anonymous Location withheld

GRAPH OF THE WEEK

Source: Instagram Poll -- December 2022

WORTH A PEEK

For those of us who struggle with procrastination (almost everyone), sometimes it seems like nothing will help. Well, we came across an article – two articles actually – that break down procrastination and why we do it and how we can stop in a silly, but extremely helpful way. It’s the best procrastination article we’ve ever read. There are two parts. Start with part one here, then move onto part two, and watch your productivity explode!

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 doubt this is something you guys can even help me with but here goes: I had the perfect sales job. The PERFECT sales job. And I stupidly walked away.

This was about eighteen months ago. I had worked at this company for just over a year. We had good leads coming in, and the comp plan was ridiculously good. I was making close to 150k a year and barely working forty hours a week. Not only that, but management was super hands-off with us, totally understanding when it came to any personal issues, and catered lunch two days a week.

Then a friend from a previous job told me about this fast-growing company he had just started at and said they were recruiting for their sales team and it would be a great opportunity as all the new reps would end up with their own teams, and basically talked me into interviewing. They offered me a higher base and it seemed a bit more exciting so I went for it. And it’s not that it was bad, but it was just super disorganized, and I ended up leaving after about four months for a bigger company, which is where I am now.

My current job isn’t terrible, but both of these roles (and the ones I had before) are nowhere near as good as the one I walked away from. I’ve reached back out to my sales manager and he politely told me that they’re not hiring right now, so it doesn’t seem like I have any chance of getting back in, especially with how the economy is doing.

Do you have any advice? Is there anything you think I can do to get back to my dream job, or did I screw it up forever? Thanks in advance.

Regretful in Massachusetts

Dear Regretful,

We’ve all been there. Seriously! The grass isn’t always greener, and sometimes we have to find that out the hard way.

Here’s what you should do: take the time to compose a nice, clearly-written email to your former sales manager. Explain (in detail) that this was by far the best job you’ve ever had, that you made a mistake by leaving, and ask for another chance.

Will it work? Maybe. But it’s really your only shot.

If it doesn’t, then it’s time to move on. Sitting around and regretting things you’ve done and pining for the past is a pointless exercise. Unless you know someone with a DeLorean that has a Flux Capacitor, there’s nothing you can do to change what happened. You can only look forward, not backward.

And, while this might be difficult for you to believe, there are other sales jobs out there that are just as good as the one you left. Yes, they’re harder to find and don’t come along every day, but it’s not impossible to find a good work environment, a competitive comp plan, and some free lunch. (Check out the jobs link in our footer for some examples).

So give your old company one last try, and if it doesn't work out, then do yourself a favor and move on. Good luck!

Quiz Answer: B – Metrics, Economic Buyer, Decision Criteria, Decision Process, Identify Pain, Champion

SHARE THE QUOTA

Help us grow, and we'll send you a reward!

{% if subscriber.custom_field['RH_REFLINK'] != '' %}

Share The Quota, get cool stuff!

Know a salesperson who’d love The Quota? Give them your unique referral link (below), and we’ll give you some awesome rewards when they subscribe.

facebook

twitter

PS: You have referred people so far

{% endif %}

How did you like today's story?

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

Was this email forwarded to you? Sign up here.

Looking for a new gig or to hire for your sales team? Check out our jobs board — powered by RepVue.

Advertise with us

Books

QUOTA MEDIA LLC

651 N. Broad Street., Suite 206
Middletown DELAWARE (DE) 19709
USA

Unsubscribe | Change Subscriber Options