Sydney Senior

Member

Happily Ambitious

A podcast about balancing achievement, expectation, and fulfillment in the world of SaaS, Sales, and Entrepreneurship. New episodes weekly.

Co-Host

RevGenius

RevGenius is a group of revenue generating Sales, Marketing, and RevOps professionals brought together to learn, share, support, and grow with each other. You can consider us your alt work family!

Deel

SMB AE

Sell Better 

Daily Sales Show Host

Falkon

Senior Business Development Representative

Pavilion

Chili Piper

Product GTM Manager

Associate GTM Manager

Trailblazer SDR

Chili Piper is the leading inbound conversion software, used by top B2B revenue teams like Intuit, Twilio, Spotify, and Gong.

We’re on a journey to build the best company to work for and to work with while trying to make the world a better place. Our team is distributed around more than 160 cities and 35 countries around the world. Join the movement!

Sales Development Representative

Brand30

Zgraph

- Conducted sales needs analysis with new and prospective customers
- Developed solutions based on specific client needs
- Maintained existing relationships with clients through regular communication and outreach

Account Executive

Kerigan Marketing Associates, Inc.

•	Certified in Google Ads and Google Analytics
•	Managed social media accounts and Google Ads marketing accounts
•	Created monthly performance reports for clients
•	Assisted with new website development and content migration

Social Media Marketing Intern

demystifying success & happiness | co-creator of Happily Ambitious | SMB AE @ Deel | building in public | mindset + productivity | Sell Better host

Feeling lost, stressed, burned out, or unable to get off the achievement treadmill?

Want to take design a life you actually love, but don't know where to start?

One of my biggest passions is demystifying success & happiness.

I've spent a lot of my life working incredibly hard (past the point of burnout) and still not feeling satisfied by my achievements, feeling like achieving one goal only meant that the goal post had to be moved further away from the next one.

While I'm far from having figured this out, I co-host a podcast (Happily Ambitious) and a companion newsletter (The Ambitious Breakthrough) to learn from some of the best in this area and share my journey as I go.

My goal is to build in public - through my role in SaaS sales, as a podcast host, as one of the founders of a growing community, and as someone who very frequently deals with all of the stressors described above.

Netradyne

Enterprise Sales Manager

Commsor 🦕

Head of Mid-Market & Enterprise Sales

Salesroom 

Sales Director

Head of Enterprise Sales

Jamf

Strategic Enterprise Account Executive

A lot of places

Career in Physical Fitness and Rehabilitation

Bob the Builder of Pipeline | Cold Calling Mercenary | Sales and Humor | Voted “#2 Best Parent” - by my 2 year old 🤷🏻

Welcome to my page - where you’ll find my best attempt at bringing some humor along with some fun facts and GTM tips and tricks!

We can all agree that life is typically too serious and stressful, especially on a professionally based platform, so I enjoy breaking that norm with some laughter in both my content and sales process.

Professionally: I specialize in building and refining sales motions and top of funnel processes, bringing a unique twist that “breaks through the noise” of the modern day dreaded norm of what people believe is good revenue generation.

Before moving to Sales, I had the pleasure of coaching and treating thousands of clients through rehabilitation and personal training for almost 10 years, where I now channel the same energy and passion in leading GTM teams.

You’ve scrolled this far, we might as well get to know one another.

I’m a redneck working a white collar job living in a blue collar state 🥔

“When you turn a passion to a profession and truly love what you do, then you don’t work a day in your life.”

💥I’ve been lucky enough to do that twice💥


↙️“About me”↘️

Mission 1: To push past the “limitations” that your mind sets whether it be physical or mental.


Mission 2: To build my career in Sales and build a bridge between my old world of fitness and apply those principals to the business world.


- Constantly looking to learn. Go spark up a conversation and learn something about them and that little conversation could change your life. 

- “You don’t know till you try” I find to many people (myself included) stay comfortable and are afraid of breaking complacency.

- There is no greater feeling being coached or better yet, coaching someone else, and watching them succeed.

Eric Iannello

I instantly lose trust to any person who exercises during a work trip


“Were you able to snag a few hours of decent sleep at the hotel last night?”

Oh yeah it was great! I got up early, went for a run, had a good meal and got to the office early. How about you?

“What’s wrong with you? I barely slept because I stayed up all night watching what ever movie I wanted without my wife or kids fighting me. Then I took a bath this morning for no other reason than I could. And I hate baths! I almost missed the complimentary breakfast but still managed to squeeze in 3 servings simply because it was a hot meal, hence why I got here 15 minutes late”

Umm, ok then

“Wait…does that mean you consciously packed workout clothing?”

Yeah, I’m on this super strict plan that…

“Get the hell away from me Stuart”

0x PClub | 0x Exits | Voted “#2 Best Parent” - by my 4 year old 🤷🏻

I left the Zoom call within the first 2 minutes because of what the rep was wearing

Remote work has set in some bad habits and wearing a hat is the top of the list!


Please excuse my crossed eyes after they roll so hard when reading things like this 

Things that are far more important than caring what anyone wears during a sales call:

Their posture 

The quality of their camera 

Their background

Their picture on LinkedIn

Their picture in their highschool year book

Their choice of breakfast

The car they drive

The music they listen to

The place they live

Their favorite place to dine

And their favorite park to swing at when they were in 3rd grade

Now this tells me far more about the level of professionalism they are capable of above choosing to wear a hat


Sincerely

A father who has young kids and who doesn’t always have time to shave his head every day and prefers to wear a hat instead of looking like Dr. Phil’s half bred cousin and who has never lost a deal because of it…

3x RIF | 2x Org Close | Voted “#2 Best Parent” - by my 4 year old 🤷🏻

When they know their written content sucks

No alternative text description for this image

My morning routine in order to achieve peak mediocrity:

4:29 wake up from kid crying
4:35 realize I’m up for the day
4:40 make coffee with my tears
4:48 head to 🚽 after coffee hits
5:10 try to get the feeling back in my legs after sitting for to long
5:26 pour second cup of coffee with a dash of whiskey
5:27 laugh at people posting their mourning routines on LinkedIn 
5:45 walk to fridge and contemplate having Dino nugs for breakfast because, f*** it
6:02 hear second kid wake up and realize its about to get real
6:11 pour glass of whiskey with dash of coffee
6:30 contemplate becoming a forest ranger in shower
6:48 hide in closet till family goes downstairs
7:02 begin writting resignation letter
7:06 delete resignation letter after hearing kids laugh and begin to regain hope
7:23 walk down stairs and begin the day



Course link in bio

Everyone: Parenting is the hardest job 

LinkedIn: Well you clearly have never tried cold calling during the holidays…

If I see one more, just graduated, never carried a number, learned how to spell AI yesterday, kid 

Tell me I have a lead gen problem…

…I’m flipping this table

This may ruffle some feathers

But you know who’s not going to get hired?

The folks who treat their job search the same as they did 2-3 years ago

It’s so sad to log on here and see people post that they’re about to lose their house after submitting 600+ applications

*Also why everyone should work in hospitality and sales at least once in their life
Boy, do they prepare you for the real world between understanding a grind and how to sell a product…or yourself*

In order to land a position today, at a minimum, you need to:
- Connect like a sales person at a convention
- Constantly build and engage with a network 
- Attend events and be apart of communities
- Be the first one in line but also stay after closing 
- Be creative and make yourself stand out
- Be a step ahead and lead the process
- Ask the dumb questions and let curiosity leave no stone unturned
- Be resilient beyond belief and dont let the “no’s” knock you down
- Prepare for anything

And above all, lead with confidence

*whispers nicely so to not hurt people’s feelings* kind of like sales today…

If you’re just submitting a resume, what does that show the hiring team?


Sincerely,

Someone who has been through 2 org closures, 1 RIF and 1 product rebuild, all within the last 3 years, which has left him with a resume that looks like Nicholas Cages acting career

Bob the Builder of Pipeline | Sales & Humor | Voted “#2 Best Parent” - by my 4 year old 🤷🏻

I love it when I see people put their achievements in their heading

14x presidents club

Top 2500 Sales Leader to follow

$1M-$2B ARR in 42 days


I’m going to start walking around with medals around my neck with all my achievements 

“Voted #2 Best Parent”

“Saved more than 15% on my car insurance”

“Put clothes in dirty hamper x5”


Next im going to have a name tag with all my {ex’s-name} on it

I may need some more name tags…




Course link in bio

Do you feel stupid when you leave a comment and they don’t DM you the secret?

Or just when you do get it and realize it’s worthless

I scored the most touchdowns during a single season in highschool

“Get over it dude! The heydays are gone…”


I drive a brand new sports car and have a huge mansion 

“Wow, can you believe the ego on this guy?”


Presidents club 4x, 2 Exits, ex-Meta

“Oh…my…God, this is gold!”


LinkedIn logic…

Just when you think you’re on top of your game

Rippling goes and shows you how to really troll

 
Well played team

Absolutely well played



Your move Deel…

Literally no one ever


Everyone on LinkedIn:

“Want to know how I’m better than you?”

Lately it’s been feeling like I’m lost for answers

My oldest recently turned 4 and is becoming amazingly more aware…and curious

Most questions having simple responses like

“Why is the sky blue?”
- well, the earth is made up of mostly water and it’s a reflection of all the oceans

“How fast can a person run”
- Somewhere between 15-20 mph but your dad can run 30 mph!


But then there are those that just make me sit there, lost, trying to find the answer myself

“Hey dad, where does pipeline come from?”

….

Remember kids

It’s not the algo

Your content just sucks

Happy Thanksgiving!

Hey Chat GPT, give me a post that’ll generate a ton of engagement

“Hold my beer”

Steps to writing a post that’ll feed your dopamine craving

1.) victimized story
2.) half baked correlation to profession
3.) selfie 
4.) offer a course

What selfie should I choose?

“Pull open your camera feed. Close your eyes and scroll. Count to 3 and then stop and place your finger on one. That’s the one”

That’s it? That’s all I have to do?!

“Yup”

What about creativity?

“Ha”

Ok, anything else?

“You should tag someone popular on here too, just in case”

What if I don’t know them?

“So…you’ll get so many ‘this is gold’ comments it’ll make your hair grow back”

Wow, thanks chat! I guess I’ll be back tomorrow for another

“I got you fam”

I built an AI agent that scans all of LinkedIn and downloads every course offered

It then scans the course

Summarizes the content 

And then builds a GTM motion according to its instructions

I haven’t booked a single meeting or closed any deals with it…

But it took me just shy of 32 hours to build but you can have it for free!

Just comment “we are doomed” and I’ll drop you the link

You must first be connected with me and my neighbor Stuart in order to get it

But before that, make sure you’ve tickled a pandas big toe on Sunday and then counted to 735 while in a head stand

Didn’t know I had a newsletter?

Idiot 

Of course I do and it’ll change your life

Follow Eric Iannello for more useless tips

I’ve been on LinkedIn consistently for 2 years now

These are the facts Ive come to learn about this platform


- Networking is the single greatest thing you can do for your career, no matter the industry 

- Most who post are looking for validation rather than trying to deliver value or teachings

- There is a ton of great learnings on here, hidden deeep down in the scroll

- Follower count is an illusion. Between automated sequencing tools and engagement bates, follower count usually just points to the fact that they post stuff that drives vanity metrics

- People need to go outside and take a big breath of reality before posting

- Free courses and selfies are mainly useless ploys to drive your attention, not value

- Agree in public but disagree in private 

- We have no idea what we’re doing but we sound good

- Cut all result “claims” in half, maybe more

- They aren’t dumb, just disconnected

- It’s not a podcast, just a Zoom call with a fancy mic and a lot of head nodding

- Everyone has an angle

- “Qualified” to write on a topic is a manner of interpretation - check your receipts! 

- It is was you make it. You treat it like a networking platform, it will be. If you treat it like social media, it will be.


Any I missed?

This time last year, right before Thanksgiving and my second kid was born

I was laid off 

No warning or severance

Healthcare was shut off the next day

“We’ve run out of runway”

I thought you told me I had 4 more months?!

“Today is sadly your last day…”


And then again, the November a year before

“We’re not going to be able to cover this month’s pay period, we’re still waiting for investor funds to clear”

It’s been 3 months since we’ve been paid! This is insane, I’m a single income family, come on {CEO}

“You think you’re hurting?! I have $1M of my own money invested in this company! You knew what you were signing up for when you accepted a position at a start up!” 


And then the year before that…

Yup, you guessed it

“Eric, we’re going to move back to founder sales”

Wait what, why?! I just hired another team after you let the last one go?

“Please start to conduct their exit interviews and yours will be held shortly after. You’ll be covered for 2 weeks following your departure…”


I’m sure there’s a lesson in here, somewhere 

Wouldn’t be a LinkedIn post without one

Something like:
- do the deepest due diligence you can into the company you’re joining
- always be prepared for the door to get unexpectedly closed on you
- build a network strong enough to shorten the gaps between employments


Q4 is the “weirdest” time of year for sales people

You get happy holidays vs missed annual benchmarks vs possible layoffs

If you have a twitch in your eye or some weird heart palpitations because 69% of sales people are due to miss quota on an annual scale this year

You’re not alone

I couldn’t believe what I heard

My son storms into the house and yells 

“Mom! Dad made me lose a fish!”

How did your dad make you lose it?

“He CUT my line while I was reeling it in”

My wife turns to me like I just canceled our Disney+ subscription

“Why on Earth would you do that?!”

Calmly I explain

Now hang on just a second - it was probably a monster, and watching him reel it in reminded me of all the deals I’ve lost at the finish line. 
The ones that were ‘committed’… until they weren’t. So I cut the line trying to prepare him for the real world.

“Babe, for the last time, B2B sales isn’t the real world!”

Log on to LinkedIn just once and you’ll see you’re wrong…


Anyways, I’m currently shopping for a new couch, this one isnt comfortable to sleep on

Any recommendations?

If you choose to conduct staff reductions during the holiday season

You should also choose to kick the corner of the couch with a barefoot

…repeatedly

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The Battle

Sydney Senior

Eric Iannello

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The Battle

Sydney Senior

Eric Iannello

Followers

Posts

Engagements

Likes

Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Eric Iannello's LinkedIn Performance

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