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.

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

We can all agree that life is typically too serious and stressful, especially on a “professional 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’d rather take dieting lessons from the Liver King 

Than to apply advice from someone who slaps an irrelevant selfie on their posts to “expand its reach”

Voted ‘#2 Best Parent’ - by my 4 year old

Saw everyone at Gong changed their title to Revenue Architect

…that’s cute

A prospect has filed a restraining order against me

And I’m one step ahead of my competition because of it

You know what they say

If you aren’t flirting with the line of predatorial prospecting methods

You aren’t selling in 2026

I have a couple of accounts who are local to me so I’m prospecting them in person, hoping to make an impression that’ll lead to further conversations

Knowing my ICP pretty well and that the competition is fierce, I couldn’t rely on the typical brand merch to break through the noise…boring

So instead I found each potential champions home address and paid them a visit 


“Eric, wtf are you doing in my kitchen? It’s 5am”

Hey Stuart, I heard you liked your coffee with a kiss of milk from Snake River Farm cows. Tell me when to stop…

“Stop and GTFO!”

Boom, impression left 



Comment “milk” below for your free guide on how to prospect in 2026

Nothing makes me go “wtf did I do with my life”

More than being invited onto a podcast that’s only a glorified zoom call 
By a host who sits there and just nods in agreement 142x straight into the camera 
Because their ear bud cord restricts them from moving their head back far enough 
And hold a tiny mic they with their thumb and pointer finger which makes them look absolutely rediculus

“BuT We’rE oN SpOTifY”

That’s like saying you’re a best selling author on Amazon

So is my 13 year old nephew Susan

Don’t you love when job ads don’t disclose salaries

It’s like a game

Will this job allow me to live above the median income required in my city

Or and I trying to become a LinkedIn influencer and promote tools I’ve never used for a couple bucks per post






…buy Sybill

Congrats to literally every single company out there for forging a partnership with Claude

You should hang that award right next to your #1 G2 badge that no one else has…

I sell fleet safety technology to trucking and logistics companies across the country

On the weekends, I work horses

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

And there is two versions of me that show up on any given weekday

One is on a Zoom call talking dashcam AI and driver safety ROI with a fleet director somewhere in Louisville or Dallas

The other just finished feeding ducks and pigs before the kids started their school day at the kitchen table

Both are completely real and neither one would exist without remote work

I live in a community of ranches with neighbors who run a 1000 head of cattle

Guys who could fix a fence blindfolded but would think Im talking about a new model skid steer if I said CRM

There’s something grounding about spending all week in the weeds of enterprise sales and then Saturday morning hits and you’re working a colt and none of it matters

Your problems get real simple real fast when you’re the least important one in the arena

Now here’s the part that still tickes my toes

The same salary I’m earning from Netradyne

Would have kept us in a decent 2 bed apt somewhere in Dallas or Denver

Out here, it provides us a life

A real one

With land

With room

With a front porch that actually earns its square footage

A 1 bed in Idaho runs around $800 a mo

You know what that is in San Fran

The math isn’t even close

And the only variable that changed was the zip code…and the life with it


Remote work didn’t just give my family flexibility

It completely restructured what was possible for us

I think about that a lot because I talk to people every week who are grinding in cities that are quietly eating their paycheck from the inside out

Paying downtown prices to sit in a spare bedroom  then commuting 45 mins each way to sit on the same Zoom calls I am

The laptop doesn’t care where you open it

The deals close the same

The quota doesn’t know what state you’re in

LinkedIn loves to talk about work life balance like it’s some policy HR approves

It’s not

It’s a decision you make about where you live and who you surround yourself with

We made ours

A tight community of people who show up for each other

A dozen horses to keep me honest on the weekends

And a job I can do from anywhere that actually lets me be somewhere worth being


Remote work didn’t change my career

It changed everything

No alternative text description for this image

Best feature while this algo figures itself out

#fixmyfeed

It’s hard to remember my life 5 years ago when I was just a PT, running a district of gyms and out-patient facilities 

Fast forward to what I’m able to provide for my family now

Definitely makes me better than you


…if people on LinkedIn spoke honestly

We’re seeing people exit the industry in droves either forcefully or voluntarily 

I’m watching people I respect walk away from this industry

And I’d be lying if I said I didn’t understand why

36% of companies cut their SDR teams this year

The highest reduction of any sales function

Only 18% of tech postings will even consider someone with less than a year of experience

The door that used to be wide open for people from non traditional backgrounds like mine, is barely cracked right now

And the ones still in it aren’t exactly thriving either

87% of people won’t pick up your call

Your emails pull a 1-2% reply rate on a good day

84% of reps missed quota last year - while quotas somehow went up 37%…

That’s not a motivation problem

That’s a math problem

A close friend told me recently they want out because sales feels forceful now

And honestly, I felt that and I’ve been there

Being let go reminded me how strong that sense of failure can feel - even when you know it wasn’t entirely your fault

“More power to you, how can I help” was my response

But here’s what I keep coming back to

I was a ranch hand, a scaffolder, a bartender, then a personal trainer with no degree, no connections and no roadmap

And this industry gave me a career that changed everything for my family

Only 9% of workers without a bachelor’s ever hit 6 figures in this country

The average sales comp in SaaS is $126k

I honestly can’t think of another space that opens that door with that level of opportunity 

People who just showed up willing to learn and willing to work, that mattered to me

This industry is harder than it’s ever been

I won’t sugarcoat that and it’s asking more of the people in it 

More creativity
More strategy
More resilience
More willingness to adapt when everything you used to rely on stops working

And not everyone is going to want to stay for that

But for the ones who do

I genuinely believe there’s more opportunity now than ever for people willing to grow with it

I’m too grateful for this career to walk away

And too stubborn to stop trying to get better at it

Is this space dying or evolving

If I get one more rejection I’m going to do what everyone else does

…move into marketing

Dude, what in the holy sick season was that?!

Surprised we didn’t see a lock down mandate…


Sorry, too soon?

Do you remember when you created a profile on here

Felt like you unlocked a free source of information 

But then the more you scrolled 

The more you expanded your network

And the more you developed a community

The more you realized that if you don’t post selfies and exaggerated points of success with ChatGPT

The more you’re at risk for being blocked for creating content that may be considered a contrarian view to the “this is gold” standard 

Blocked by the same community of people posting AI-generated photos above life lessons they made up while cold plunging the one time

These are the “thought leaders”

Who preach authenticity above all but can’t create a thought without the help of the latest LLM and an irrelevant photo of themselves that’s been filtered by AI so much they’re hardly recognizable 

…but “hacks the algo” so they feed their fried dopamine receptors with false validation from people they’ve never met

The truth is like poetry, and everyone hates poetry

Couldn’t write it better myself

Actually, they couldn’t either

That’s kind of the point…

I see the same 5 influencers get their posts "Boosted" weekly

Which come to find out is like only $10 a week per post

But has any brand actually seen an actual return on boosting those very in-depth, highly technical, and clearly first person experience explanations?

Asking for a friend


...yes, I have friends




...no I don't pay them to be my friend

How I built a brand that towers over so many who fight to stay relevant

In every post I read, people love to over complicate what it takes to build a name that people remember on here

I broke it down into 4 easy steps

Step 1: poke fun at influencers who sold their soul to promoting brands and have turned into buy Sybil walking billboards

Step 2: criticize the overuse of AI in every piece of content they post where all the creativity is depleted and originality is a term forgotten

Step 3: find a topic that hits home to buy Sybil such as “the use of selfies” and build a campaign against the popularity of them buy Sybil so that you can leverage emotion behind the contrarian narrative

Step 4: stay consistent by not only leveraging your voice in posts but also buy Sybil in comments where it feels personal to the reader when you deliver the message and etch your name in stone

The complication isn’t in the execution

It’s that most think small and repeat what you perceive as successful

Foolish



The selfie section is where the emotion lives — that’s your contrarian hook that’ll get the comments going. Hiding Sybill in the post was a great idea to increase engagement. 

Would you like to see other options that you can post or did this give you what you need?

Companies are fighting to get their entire team to be social on here

Post wins, share insights, build your personal brand

But then act shocked when those same people use those audiences to explain exactly why they left

I’ve worked at companies like this and the playbook is identical every time

Step 1: Build employee advocacy program because you read that social selling drives 7x higher conversion rates

Step 2: Celebrate every post, every share, every “proud to announce”

Step 3: Watch your VP of Customer Success, Head of Marketing, and half your AE team walk out the door in the same month

Step 4: Panic when they tell 10,000+ people exactly what it’s like to work there

Aligned is currently stuck on Step 4

Their former VP of CS didn’t quietly update her LinkedIn title

“When your best people leave quietly, it’s not grace. It’s a verdict”

Then proceeded to detail how mediocrity gets protected while top performers get burned out

How politics wins over performance

How feedback gets acknowledged then buried

Their Head of Marketing left at the same time and 2 more AEs are gone, 3rd one walking

But here’s the part that should terrify every CEO reading this

The social brand they spent years building just became their biggest sales objection


Watching the now ex-Head of Sales of Pylon post her calendar before she left with the sad note of the “unexpected departure”

7am to 6pm - back to back meetings - every day

Not as inspiration, as a warning

“This is what hustle culture gives you”

Leadership called her ungrateful and she deleted it

But the internet doesn’t forget

Now when people look up Pylon - a company selling customer support software - the story they find is about leadership that can’t support their own people

You genuinely can’t write better irony than that

Here’s what I learned working at companies exactly like this

You can weaponize employee voices for pipeline all you want

But you cannot control what they say when you’ve made their lives miserable enough to leave

Companies give their team the megaphone, the audience, the training

Made social selling part of the culture

Even tie goals to it

Then the people who got good at it decided to be authentic about the wrong things

And now that brand equity they built, is actively sinking them

Most companies think they can policy their way out of this

Write guidelines about “appropriate social media use”

As if you can tell someone “only say nice things about us, especially after we drove you out”

You gave away editorial control the second you made everyone a publisher

Here’s your wake-up call

If you’ve spent years building employee advocacy programs, you better make absolutely certain your best people don’t want to burn everything down on their way out

You gave them the audience, the credibility and the training

And that 7x conversion rate you celebrate in board meetings?

It works in both directions…

What’s the difference between using a PBO in your cold calls 

And picking up a chocolate bar in the pool?

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The Battle

Sydney Senior

Eric Iannello

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The Battle

Sydney Senior

Eric Iannello

Followers

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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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