oldcloser

💀

AMA with OldCloser: 40 years in the sales saddle. Still love to ride.

If we, as humans, are defined as the sum total of our experiences, I’ve got some total.

I learned to sell on the phones at 16, after school, making appointments for in-home attic insulation pitches. -OG SDR- Since, I’ve held just about every sales org title. Got my first P-Club selling newspaper advertising in 1990. My first 7-figure deal was an AM radio Dodger baseball contract. Hopped to the Howard Stern Show in ’92 and went 0-100k MRR in 7 months.

First management job in ’94 running the Stern sales team in the Bible Belt, Dallas, TX against a market wide advertiser boycott. $4M to $7.2 ARR in 3. First VP title in ’98 at what’s now iHeartRadio. 0-$13.3M in year one. Opened and ran my own ad agency for 12 years, until I met full digital disruption. Tech went right past me. Caught up to it and fell in love with startup chaos in cable TV. Martech, Fintech and ML followed. If I could change any of it, I wouldn’t.

❤️ Bravado Community

101 comment

Sort by:

antiASKHOLE

Tycoon

Bravado's Resident Asshole

You really are an “oldcloser”. The name isn’t a gimmick at all.

I have been a big fan of all of your feedback since you joined in the WR. If you could sum up your “some total”, what would be the overall piece of advice you have when it comes to sales?

oldcloser

Arsonist

💀

Appreciate that- and yeah, I’ve been around. The one key to longevity in sales is this: The only thing you have, when the smoke clears and the dust settles, is your name. Reputations are built over time, but they get trashed in one greedy move. When you’ve got a glaring opportunity to “high gross” or take advantage of a situation, just don’t. If you’ve got any mastery of this craft, clients will remember you much longer than the solution you sold them.

You’ve put up a glowing example of this lately.

antiASKHOLE

Tycoon

Bravado's Resident Asshole

So in short, don’t burn bridges unless you absolutely have to.

oldcloser

Arsonist

💀

High road out. You don’t ever have to.

HVACexpert

Politicker

sales engineer

Wow what a work history! Bet you have a lot of war stories.

Which job was your favorite and why?

oldcloser

Arsonist

💀

When I got my first set of VP stripes, I had a boss who was 100% hands off. I had total autonomy and a local staff of 18, including a Local Sales Manager and a National Sales Manager, plus the 40 rep offices he managed. Day one on the job I was just straight freaked out. The responsibility was huge and I'd never seen revenue expectations like that. Corporate wanted $6M from a brand new radio station.
But I quickly grew into it and just got really freaking busy. Inventory management was a thing back then, so when a radio station gets ratings, that and demand drive price. I found myself having to raise prices every 2 days to keep from committing the cardinal radio sin, selling out.
I had a vet team and a new product that was on fire. Banana Joe in the morning used to say shit like "Merry Christmas, kids. And if you caught daddy with his pants down in front of the computer, he was just shopping." First 60 second rate was $50. It went to $700 in 90 days and we delivered $13.3M. Most fun I ever had.

Beans

Big Shot

Enterprise Account Executive

I'd love to hear your experience during the dotcom bubble and the '08 market crash.

What trends carried through both that resonate today?
What industry were you in, how did it react?
How long did the "feel" of the market take to turn around and buyers wanted to buy again etc?

oldcloser

Arsonist

💀

Dark era for me - both of them. I was one of the sheep chasing the dot com dream. I left corporate radio in Dallas, got my ass in a car and drove to SF. Went to work selling eyeballs at Salon com. Figuratively speaking, I didn't understand why the line of cars going the other way was so long, but I was going to conquer the web. Kept my house, wife stayed there while I went out pioneering.
Started to stack up clients at the end of the insanity... until this thing call CPC and CPA showed up. Almost immediately, the CPM model dried up and it got really difficult. Layoffs started, but in those days, sales was last to get it. Ended up staying about 9 months before blowing out and going home. There is just no beating those kind of macro economics.
I wasn't really "feeling" anything until "we don't buy it that way any more" showed up. Then it was abrupt. Was a defining moment for me. That's when I pitched my own tent selling conventional marketing to car dealers. Totally turned my back on this internet bullshit. I thought it was ill-conceived. Who knew.
'08? Another one. I had a healthy client roster that basically vanished over night. I was in deep shit. It was 3 years of selling one-offs and stringing shit together just to keep it together. I never actually felt and end to that one from that perspective because the ideal of doing what I was doing wasn't sustainable. My run had ended. That's when the web came back and said, "Hi fucker... wanna go again?"
I closed up shop and went to work at a startup cable network, put together a sales team and climbed out of a really deep personal hole. When the station GM called to offer me the job, my cell phone was turned off. I only saw the offer via email. Had to call and tell him my phone was hacked.
Stringing together a lesson through this: Don't ever be scared to bet on your own talent. What got you there will sustain you through anything. It has to.

I really hated this question, @Beans - glad you asked it though

Sunbunny31

Politicker

Sr Sales Executive 🐰

So many things to ask! I’ll start with this: looking back over your career to this point, do you have a favorite deal/sale? And if so, what made it great for you?

oldcloser

Arsonist

💀

I do have a favorite deal!
Getting off a plane in November of '01 to go pitch my agency to a really big Honda dealer. I walk over to get in line at the Hertz counter. First thing I realize is there is no line. OF COURSE there's no line. Nobody was flying after 9/11. And because nobody was flying, nobody was renting cars. Because nobody was renting cars, every single car rental company was teetering on bankruptcy. I get my keys to the rental, get in and look down. Noticed the car had 17 miles on it and smelled brand new. So.... as I'm running through my pitch on the way over, my light went on.
Typically, when a rental hits 30k miles, they're sold at wholesale to franchised new car dealers. But these new cars were sitting in rental lots with the companies paying huge interest for them as they sat. This was actually a crisis.

So, I conjure up this thing called "carrentaldisposal.com" and pitched it to the Honda store like this: "Attention Phoenix, THIS. IS. A. PUBLIC NOTICE. Due to the airline crisis the rental car companies are in trouble. You can now buy late model, low-mileage vehicles for pennies on the dollar." The dealer says, "can we be the exclusive rental car disposal outlet?" I said, "yes, for three days only, but you absolutley have to put up a fence and show cars by appointment only." Then he says, "can we extend the event the following weekend?" I said, "of course! Let's do 3 weeks."
He approves a $200k budget and we let it loose. He sold some 400 used cars that month for an easy $2.5M in gross margin. I took that idea around the country and sold it to no fewer than 40 other dealers. It was the gift that kept on giving. I was a 3 person operation at the time. The party lasted for about 18 months.

I still tell this story in interviews. The moral? The bigger the idea, the bigger the sale. Honestly, I haven't had one that good since.

Sunbunny31

Politicker

Sr Sales Executive 🐰

That is an amazing story! Seriously brilliant idea, too. Making a sale relevant, solving a problem.

oldcloser

Arsonist

💀

Thanks Bunny- that’s the moment I learned the value of an idea.

Sunbunny31

Politicker

Sr Sales Executive 🐰

That was a true brainstorm. Must have hit you like a bolt of lightning. So true, so obvious, so simple - and no wonder your customer grasped the value. It made so much sense. What an opportunity!

oldcloser

Arsonist

💀

It was a rare floodgate moment. I wasn’t entirely sure it was even legal when it came out all over their conference room table. Their buy in validated it entirely. Crazy moment. My take on that deal was $40k. Almost had to find a bathroom on the way out. 😂

Retired Sales Professional

Same sentiments as Anti here oldcloser, I haven't been here that long but your insight into your craft is spot on and enjoyable to read and also to learn from

My question is who were your biggest influencers that made you who you are today?

oldcloser

Arsonist

💀

Two managers stand out. The first was a woman who was the most intense monster I've ever met. She used to call me asshole. Was my first management gig. "Come here asshole. What the fuck were you thinking with this deal?" I never had an answer that held up either. "Well, I was thinking that...."
"Do me a favor, stop fucking thinking and do things the right way."I took it, because she was honestly the sharpest negotiator and most talented straight driver that ever lived. When we broke the station's revenue record in year 2, she started to give me the reins. To this day, I am grateful for that woman.

The next one was the polar opposite. I referenced him in the reply to @HVACexpert . Dude knew how to handle me also. Plenty of rope, but always watching out of one eye. This guy taught me how to recognize talent, then set it free and let it soar once it takes off.
Thanks Frank

Retired Sales Professional

👍👍

Sunbunny31

Politicker

Sr Sales Executive 🐰

Holy cow. That first manager is the blueprint for every tough guy cop captain out there in television.

oldcloser

Arsonist

💀

She was living with a guy she was supposedly was engaged to. Then, she later came out and most things started to add up. Brilliant freaking human. Just angry.

GDO

Politicker

BDM

damn, never expected the name to be so spot on.

oldcloser

Arsonist

💀

Keepin’ it real 💀

CuriousFox

WR Officer

🦊

Southern. A distinguished gentleman.

oldcloser

Arsonist

💀

Thank you, ma'am.:::::belch::::::

CuriousFox

WR Officer

🦊

🦡

BTQ

Politicker

Account Manager

I always appreciate your feedback in here. Has helped me move the needle in a few of my deals moving forward or at least getting an answer.
How has the SDR role changed since your days as an SDR compared to today? How does the average SDR from the dinosaur days compare to now?

oldcloser

Arsonist

💀

Generally, its the same, but the tone today is so different. We used to get all kinds of animated. Manager at the front of the room looking at us-- "I want to hear an ENTHUSIORGASM!!" "Get pumped up boys! Next appointment pays a $5 spiff!"
The room would go wild.

BTQ

Politicker

Account Manager

I cant imagine calling on a floor man. My GF has to call for her job sometimes and I can't focus when we call at the same time lmao. Crazy shit

oldcloser

Arsonist

💀

People used to hang up when they heard the chatter. Was a thing.

Kosta_Konfucius

Politicker

Sales Rep

Insane background, curious how do you keep yourself industry agnostic and working a wide variety. Especially how do you show you can succeed in the early stages when selling in a new indsutry

oldcloser

Arsonist

💀

I guess over time the self-merchandising becomes natural. Selling up in a new org with a new product is absolutely required. The expectations have to be set for onboard ramp. I don't think any one of us really get any command over a complex product for at least 6 months, so it's important to get that in the open from the start. And when the dev isn't done yet, that's a moving object.

I like to either bring the leadership in, to diversify the accountability for lost deals, or make damn sure they know what objections really are.
When selling an established product in an industry new to me? Yeah, that part has its moments. Worse yet, is having to train a team of sellers on a product you know nothing about and an ICP you've never met.
The easiest out for me is hyper-candor, almost to the point of self deprecating humor. "Look team. You know I just got here. I know I just got here. And we all know I don't know how to pitch this yet. I promise you, that when I develop my spin, I'll be able to add value, but for now, you gotta lead. That's just the truth. Most will appreciate it. One guy says.... yeah, they hired another stiff who can't sell. Then, over time, you prove it.
New sales managers that come in beating their chest about this and that... prime targets for back channel mutiny.
Long story short, own what you don't know. Then know it as fast as you possibly can. Those early days require long hours.

jefe

Arsonist

🍁

Thanks for stepping up to share your wisdom, @oldcloser ! You've been around the block and back again - a few times...
In sales, many of us have found ourselves in a toxic environment at some point in our careers. Have you had any experience with this? If so, how did you deal with it, and what kind of advice can you offer others to handle it and keep moving forward?
Do you have any thoughts on the best way to avoid this?

oldcloser

Arsonist

💀

I guess toxicity comes in all kinds of different forms, but the common thread is always ego. I have no tolerance for bluster or bloated bullshit from management, so my encounters have always been short. The best sellers in any org are always politically agnostic and keep their head down. I always tried to model that, but when it gets too thick, I'm out.
This is a great question. I have no idea how to manage within toxic environments. I just go into self preservation mode and GTFO.

jefe

Arsonist

🍁

It's not shocking that this would be your approach!
Have you had any times where you sniffed out this toxicity before coming aboard? If you have, how'd you do it?
I imagine you're asking a ton of questions during your interview process.

oldcloser

Arsonist

💀

It's hard to get a grasp on the environment before accepting any role. Even if you can, you still have to weigh potential bullshit against need for employment. I think we've all gone into jobs bright-eyed and willing to accept a less than perfect dynamic due to economically induced circumstance.
The worst thing about this dilemma is that it is just so freaking common. VCs have really trashed what could otherwise be the average "decent place to work."
This is a great question that I hadn't really thought much about 'til now. So, having just dropped my kid off at school, here's the verdict. The Peter Principal. You know this one? It says that in every organizational hierarchy, people will ascend through promotion into a role where they are completely incompetent (paraphrasing). This is real and more alive today than ever.
"Kill that VP of Sales! He's useless! Promote that guy! Jim knows how to get it done!"
Then, Jim accepts the promotion he's worked hard to earn. His CEO tells him - "more headcount! more heads = more sales. We need to raise another round! Get on it, champ! Congrats on the promotion!"
And here we are. Jim has not only never conducted an interview, he has no clue where to even start.
My point? Look for this phenomenon in the hiring manager. You see it? You run. People who only appear to not know what they're doing, don't know what they're doing. It's rampant.

braintank

Politicker

Enterprise Account Executive

Did you ever meet any members of the whack pack?

oldcloser

Arsonist

💀

Gary DelAbate is a collector of old animation art. I had an animation art dealer in LA who used the Bababooey endorsement. Was magical. And yes, as a result of that, I spend many evenings with them at The Mens Club in Dallas. Howard brought the big wad of ones. :)

SoccerandSales

Big Shot

Account Executive

Seems like you have a ton of experience and a lot of successes. What keeps you motivated to do more?

oldcloser

Arsonist

💀

Dopamine first. I still haven't figured out what feels better, closing a deal, or teaching someone to close their own. Two different levels of gratification. Otherwise, I've just always been wired this way. I don't know any other way but to grind. Always chasing a new way to win.
I think most of us have some variation of this kind of sales addiction.

SoccerandSales

Big Shot

Account Executive

Completely agreed on the dopamine, but as someone 3 years in, I do tend to get concerned it might wear off one day

oldcloser

Arsonist

💀

Unlimited supply for life. As long as we sleep it comes right back. All clear 👍

Coffeesforclosers

Notable Contributor

Director Sales and Market Development

Love it! Great track record. Similar story for me in ad sales to tech

oldcloser

Arsonist

💀

Few make the transition. But when the writing is on the wall, you just gotta figure it out to avoid becoming a dinosaur.

Coffeesforclosers

Notable Contributor

Director Sales and Market Development

Yessir

oldcloser

Arsonist

💀

Would you go back to ads?

DataCorrupter

Politicker

Account Executive

I don't think this has been asked yet, but how has sales changed over the last decade in your eyes?
I was starting out in sales around 2015 and all these older guys had epic war stories, massive deals, and million dollar checks. In my experience, these seem fewer and further between as time goes on. What's changed, if anything, in your experience over the last decade?

DataCorrupter

Politicker

Account Executive

Also, since this is your AMA, just wanna give you a shout out as a top contributor here in the War Room. I know we don't know each other, but I'm a big fan and appreciate what you bring everyday.

oldcloser

Arsonist

💀

Visa versa and likewise, homie. You bring a ton of value. Appreciate the good words.
Funny, I think I just did a mini novel in my last reply to @HappyGilmore about what's changed. Sales is still the same basic function. It just requires so much more to get through the constant messaging that buyers receive. Not to dis the question, but please see that reply for my opinion, for what its worth.

DataCorrupter

Politicker

Account Executive

Damn that guy, he asked the same question 15 mins before me... ha.

oldcloser

Arsonist

💀

I was literally spilling it as you asked.

Diablo

Politicker

Sr. AE

Wow this guy is a rockstar.
Are you still involved in closing deals or purely on the leadership team?

oldcloser

Arsonist

💀

Currently part of a team that’s building a seedling. Wouldn’t do any of it if I couldn’t pitch. Actually learning a new vertical.

Diablo

Politicker

Sr. AE

Awesome 👏

saaskicker

Celebrated Contributor

Enterprise AE

Based on your radio experience - what are your thoughts on the unbundling of linear TV & cable today? will it go back to re-bundling?

oldcloser

Arsonist

💀

I think its toast. The 35 character limit in a Google search ad dethroned creative game. And fragmentation is slow-drip torturing broadcast television. In that industry the young are eating their parents. Take Peacock and NBC.
Big agencies known for producing the best television spots now have the biggest OTT departments. A target demographic used to be M25-54. Now, it's credit worthy M27-39 who purchased domestic beer 6+ times in the last 90, drive an EV and have show intent signals for ground beef at Costco. Hyper-targeting and personalization will only improve.
Linear TV will hang around because the screens aren't going anywhere, but the audience erosion will carry on.

saaskicker

Celebrated Contributor

Enterprise AE

spent time in the OTT world, more on subscription growth - but yes the hyper personalization thats table stakes now is mindblowing.

oldcloser

Arsonist

💀

Would you go back?

saaskicker

Celebrated Contributor

Enterprise AE

i wouldn't at the moment.

oldcloser

Arsonist

💀

You know where to find me 😁

Filth

Politicker

Live Filthy or Die Clean

@oldcloser I agree with you a lot on the reputation and name being the only thing a salesperson has but I wonder if maybe the tech space makes this harder to stand by then it used to? I find myself in situations recently where I am transparent and consultative and make good sales but then I turn around and find out in the implementation that the product I've sold isn't as far along as I was lead to believe (and relayed to the customer) from internal sources...

This leads to friction and pain, and yes, I know that comes with any implementation, but I'm wondering how you keep this name and handshake relationship in a good place when things are out of your control...I can't go fix things with my limited tech knowledge and at times my org doesn't agree with the level of escalation or changes that need to be made to make the sales already made go right.

Instead the emphasis from internal leadership is to make more sales and, "there are always bumps in the road" comments are made. With my reputation and client relationships at stake it's hard to just push forward with more sales with the knowledge that I may be bringing a client into a rough situation.

Any advice/comments for the above feels/situation?I would assume this happens in tech a lot or maybe just b/c I'm on the AM side versus AE I feel it more? Is it just my control freak showing?

Also, love your attitude you aged bastard and appreciate all the input you have on this site whether it's real advice or a quick pun or outlandish image/gif - I'd be happy to get shitfaced with you any day.

oldcloser

Arsonist

💀

@Filth You just plain get it. After my interview with the Corvette VP, I was contemplating just hanging it up and practicing my "Would you like fries with that?" pitch. You gave me the IoT puppet master manager story and lifted me right back up. Why I war room. Still grateful for that one.
As for that middle-man squash phenomenon. Yeah, the days of self-reliance for delivery are gone. You've got to rely on folks with an entirely different work ethic, come from a different generation, have a different set of priorities, and have no idea what it takes to find, let alone close a real deal. It's like being a waiter in a shitty restaurant. You guide the main course choice and the wine pairing. They put up an old pot roast and a Pabst Blue Ribbon.

For me, this is where the sale within the sale happens. When you have to re-set expectations. A few tricks in this realm - Transparency leads, always. Tell them the fucking truth, and never, ever apologize. Always ask for, and thank them for their understanding. There is something about becoming completely vulnerable that brings out the human in the frustrated human.

There's always an analogy you can connect between their growing business and yours. They will understand. It's hard to flip from the guy that's gonna save their world to the guy who can't get their problem under control, but the minute the excuses start, it gets worse.
I once tried talking a client out of a deal because we couldn't deliver. But he stuck because the tech was just too good to ignore. I was off the hook. 5 years later I sold him again from another org. They do remember.

Filth

Politicker

Live Filthy or Die Clean

HA! man it's crazy how spot on you are with this. I literally was on a call a month ago trying to tell a client NOT to use us for something b/c of issue x and y. They said they can get over it and like me/my org and would be ok dealing with the issues until it gets fixed...then of course they want things done yesterday seemingly forgetting the whole conversation. It's ok, we'll charge them for the work and eventually it will get done right but man it hurts in the middle of it when I still have fucks to give.
I do have an issue/question with the apologies...HOW DO YOU NOT APOLOGIZE?! I like this idea I just have the habit of "I'm sorry this is taking so long" or "I apologize for the issues we are seeing" how do you tackle issues without sounding like a cold uncaring asshole (I am that at times I just would prefer not to sound like it)? Is this when you do the ask for understanding? how does that look, b/c I've thanked for it but never quite asked for it.

Sunbunny31

Politicker

Sr Sales Executive 🐰

I'd like to hear how to not apologize as well - and once more for our Canadian friends for whom it's a way of life.

oldcloser

Arsonist

💀

I thought I answered this somewhere, but can't find it so I forgot to send? Could be.

I'm not advising to not apologize. I'm just saying you shouldn't use those words. Example: What happens in a prospects behavior when you say... Hey, let me ask you a question. They always stop and let you ask. You've made them the authority on something. They want to meet that mental label and answer.
Similar but reverse effect when they hear, "I am terribly sorry." That statement validates the complaint they just made, when there's a reasonable chance they're just pushing for more. Further, it opens the gate for the next ask.

"I wish this had met your expectations. I have to ask for your understanding. Certainly you've seen similar in your own org. Not to make excuses. We will get this resolved in short order."
Followed shorty after with "I really appreciate your understanding. I'm on it and will advise as progress commences."
That way, you don't lose leverage or face. You have a chance of getting some empathy. But if not, they still haven't been given a license to ask for more stuff on top of the stuff you already owe them.
Semantics maybe, but its served me well.

Filth

Politicker

Live Filthy or Die Clean

thanks my man, I'm going to integrate this into my modus operando b/c I def feel I open the gate when I actually say sorry to have to do more for less/free and then lead to more frustration or friction.

oldcloser

Arsonist

💀

My pleasure, homie.

Gasty

Notable Contributor

War Room Community Manager

My turn. I’ve been an SDR Manager. How was the SDR setup like back then? Appointment setting only? Metric-driven with funnel conversions like it’s now? Was there any “SDR Manager” you reported into?

oldcloser

Arsonist

💀

This cracks me up. No, none of this existed. Totally different era. We didn't have computers. Our leads were on peach colored 3 x 5 cards and written in pencil. Our phones had cords. When someone got animated or heated and started walking around their desk, sometimes they'd yank that bigass phone off the desk.
I was working at The Ideal Energy Company. We were calling homeowners and asking if "this was the lady of the house?" The manager's name was Michael Hughes, a bugeyed little guy who wore makeup to cover his age spots. He had a huge whiteboard and chicken scratched the nights appointments next to each rep's name and tallied the team goal too.
Metric? That was the measurement system the country had just fully denied because we had yards. Nobody wanted meters. There weren't fax machines then. Pagers were for doctors, but they were called beepers.
Absolutely zero correlation from then til now. None. Wish I could add value here, but I got nothin'.

Gasty

Notable Contributor

War Room Community Manager

Today, we're drowning in metrics and conversions. It's like living in Excel. I wish we had the simplicity you're talking about – when a good day's work was measured by the weight of your stack of peach-coloured cards, not the number of CRM entries.
Your era of sales sounds like it had more character (and characters!). Makes me wonder how much personal touch we've lost in this age of automation and analytics.

oldcloser

Arsonist

💀

You just nailed it. KPI over quota.. the current model. Takes human talent out of the game entirely. What happened to good selling? I think it's gonna rebound.

oldcloser

Arsonist

💀

"I'm grateful for your understanding" keeps the field level, and keeps you out of the way of being hammered with more requests posed as make-goods for the shortfalls. Buyers can be a bitch when they think they own you. I'm sorry puts the seller in a subservient place.

HappyGilmore

Politicker

Account Executive

An absolute legend in the War Room to say the least.
Might be a bit cliche to ask but in your view, how has selling evolved over time from when you first started on the phones to now?

oldcloser

Arsonist

💀

This! It's a freaking book to answer this one. There is no doubt it's evolved. We used to meet buyer resistance, and it was a relatively short road to get them to drop the tension level once credibility was established on the seller side.
Now, it's a whole different level. Buyer resistance still lives, but it's wrapped in a whole new layer of emotional closure due to the sheer volume of messaging buyers see every freaking day. They just close down. We've all seen it. We have to know when its happening or the buyer shuts down harder.
Been there? I have. It's that moment in a virtual pitch when they look at another screen, or mute themselves when talking to someone else. Or worse yet, when they take a freaking call. When this happens, the tug of war game begins.
Seller thinks they've got to pull harder to get the prospect's focus back. Prospect senses it and drops the rope altogether. Seller flies backwards. Probability of close? Null.
The trick to avoiding this is that the seller needs to know when to drop the rope first, before there's tension in it. When the first layer of sales adversity shows up, the seller has to run to the prospects side of the desk, get a good look at their whiteboard and start asking about their priorities. This is why decks in disco are a death wish. You just don't get the room reading time. And room reading is a skill in it's own right. I'll save the rest for the book.
Point is, its much more difficult to get and hold a prospect's attention these days. Sales success in this era is a measure of talent, not more damn calls.

HappyGilmore

Politicker

Account Executive

Really insightful stuff here. I agree with you its a measure of talent in this day in age. I'd also say too in a way buyer research going into a call from their side is fairly high from what I've seen. They'll do a bunch of research on different vendors for what they're looking to solve for before even getting on a call.

oldcloser

Arsonist

💀

100% - Its not like you can go in and just start knocking people over. They know what you do. So, a little bit of the sizzle factor is usually stolen. It's just freaking harder.

Pachacuti

Politicker

They call me Daddy, Sales Daddy

No questions. Sounds like you’ve had a fun career.

oldcloser

Arsonist

💀

I’m just a dopamine addict like most of us.

antiASKHOLE

Tycoon

Bravado's Resident Asshole

One more question... With you being in an entirely new vertical, what have been some challenges you have had to overcome? Which skills have transferred seamlessly for you?

oldcloser

Arsonist

💀

I love this question! I was initially tasked with hiring and training a team on a subject I know nothing about. Also, building out a logical process in an industry that's got deeply ingrained garbage in it is a challenge. How do I handle training a team on a subject that's a foreign object? Very transparently... Owning what I don't know and committing to know it fast is key. I immediately got immersed in industry specific training. I spent the majority of the first two weeks studying. I got low level certs, then mid level certs quickly. Once that happened, I better understood terminology and the process I'm trying to disrupt.

I did a few demos in isolation and got the marbles out. 3 weeks in, I closed a small deal, and called myself onboarded. Once that had settled, all of the sales/management/process skills just kick in and take over.
With each new role, I get better at being a transparent human. I'm not the least bit worried about getting caught not knowing something. I suppose that's because I do know enough to have an impact, even coming in blind. I think it's important in a new role to self-affirm a little bit. Like... yeah buddy, you've done this before. Let's go.

lowhangersalesbanger

Executive

Director of Sales

40 years! Any plans to hang 'em up?

oldcloser

Arsonist

💀

I just can’t imagine quitting. Not yet, anyway. Gotta admit, I have burned out hard on cold prospecting, but that’s only recent. Personal gratification shift, I guess. Just don’t have that kind of grind left. If that were a part of it, I probably would.

Fortunately, I’m in a spot where I can build something. Never been part of a successful exit. Never had shares in one anyway. That’s the last goal. This one goes right and I’m out on a boat for sure.

punishedlad

Tycoon

Business Development Team Lead

I don't really have any questions, just want to echo a lot of other folks here. I'm entering year 9 of my sales career, and really value all of your input. You're a joy to have around the WR.
I've really only been popping into share wins, been pretty head down at work recently (and it's been paying off). Will probably be more active in here come Q1 and things slow down a bit.
Cheers!

oldcloser

Arsonist

💀

Thanks Lad. We see you... keep lighting it up!

ChumpChange

Politicker

Channel Manager

That many years in ad sales!?! That makes you a true battle-tested, seen-it-all, sales emperor. I personally know a handful of people that dipped their toes in it but all of them transitioned to something else. The grind is REAL.

oldcloser

Arsonist

💀

That it is. I don’t know about the emperor stuff. I think I just have calluses on my calluses. Appreciate the kind words tho

CallMeMaybe

Opinionated

Director of Sales

you know beetlejuice?

oldcloser

Arsonist

💀

dated his wife

Shabadoo

Contributor

Head of Growth

This is gold. Thanks @oldcloser

oldcloser

Arsonist

💀

My pleasure

CuriousFox

WR Officer

🦊

You ain't chick fil a

oldcloser

Arsonist

💀

And you ain’t just a chick.

Shabadoo

Contributor

Head of Growth

This is gold. Thanks @oldcloser

LambyCorn

Arsonist

A mfkn E

fuck I missed this AMA!

oldcloser

Arsonist

💀

I"m still talkin'

oldcloser

Arsonist

💀

Always here for 🫵

oldcloser

Arsonist

💀

@Maximas did you ignore my AMA? I think I might be sadz

Maximas

Tycoon

Senior Sales Executive

How dare I,lol.Just offered Uncle G a chance to do mine but I guess I was the one that got ignored:) so I decided to wait for it all..lemme give him a shout @Gasty and do yours too!

oldcloser

Arsonist

💀

Appreciate the participation! I think, to be fair, Gasty had much on his plate. I wouldn't hold it against him.

Bravado is a community of trusted sales professionals endorsed by their customers.

Products

The War Room Jobs Salary Guide Tech Sales U

Company

About Us How It Works Blog Bug Bounty

Contact

Press Careers

If you are hired as a contract sales rep by a Bravado customer, we may ask you to prove access to the employee email account provided to you by that customer. This data will be shared with customers to track your sales productivity; customers can use this data to confirm you meet the minimum activity requirements to pay out your ramp stipend and commission.

oldcloser

AMA with OldCloser: 40 years in the sales saddle. Still love to ride.

101 comment

Related posts

Lost my inside sales support--would like to die now

Is tech sales still as desirable a career today as it was 5 years ago?

Love in the Time of Sales