Matt Schalsey

Director, Enablement

Advantive

- Built a Advantive's first Onboarding Program
- Created Product Masterclass (certification) for 14 different products at a Introductory, Fundamentals, Master and Expert Levels.
- 85% CSAT for Enablement Training
- Three Sales Kickoffs and launch Presidents Club
- Enhanced and optimized the Sales Process to make our Lead Process 12% more efficient
- Grew our BDR team from 2 to 6 and raised our booked meetings from 8 a month to 55 a month
- Built out the first iteration of our GTM Play process and creation

Director of Revenue Enablement and Business Development 

We make purpose-built software for specialty manufacturing and distribution businesses that streamline complex processes, optimize operations visibility and throughput, and drive improved quality, profitability, and revenue growth. Deeply embedded in our customers’ businesses, Advantive’s software solutions add value along the full manufacturing and distribution lifecycle.

The Enablement Squad

The Enablement Squad is an online community where Enablement practitioners can network with each other to get advice or share best practices on initiatives, programs, or events they're working on.

As a Co-Founder it is my responsibility and focus area in community engagement
and content. I am responsible for having engaging content, strategic partnerships, interactive
events, and monitoring overall community satisfaction.
● Increased membership to 2,300+ in 3 years by organic growth
● Built out strategic partnerships with vendors and other communities
● Sold the community to Workramp via acquisition in March of 2022.

CEO / Co-Founder

Badassery

Member

Kaius.co

KAIUS.CO was founded in 2023 and inspired to help those in Enablement impacted by Layoffs. We’ve worked with other major communities to bring awareness to those searching but that wasn’t enough. Now we are going to continue to bring awareness to those searching and help those companies fill those open positions. 

Where does the word Kaius come from? It’s the name of my son, who was placed with us through foster care and adoption. When researching his name it means ‘Rejoice’, which when thinking about what our goal is - we want to be able to rejoice and celebrate a new role or position filled.

Chief Executive Officer

Pavilion

Integrated Life Choices

Service Level Provider (SLP)

Responsum AI

Strategic Enablement Advisor for the development of Responsum AI

Strategic Advisor

Mosaic

Chili Piper

The founding member of the Enablement Team, I had to build structure and processes from the ground up. I worked closely with the Product Marketing team to build out customer facing materials and battle cards. 
● Revamped onboarding experience (decreasing ramp time by 45 days)
● Launched company-wide product certification resulting in a 15% lift in ARR while
reducing churn by 27%.
● Built a brand ambassador program for our sales team and CAB members to be proficient
in our sales motion while at events.

Senior Manager, Sales Enablement

Lunchbox

Main priorities included revamping the onboarding program and
continuing education for the team. Heavily focused on Partner Enablement and front line
enablement as well to expand knowledge of the product.
● Built out a product masterclass brining raising our average deal size 8%
● Revised communication and training plans, and multiple product launches
● Implemented and measured success of a new Onboarding program and Sales
Methodology

Manager, Revenue Enablement

Over a decade of direct sales/customer success experience, continuing to master all areas of the customer buying process. From sales education, change management, philosophy building experience. I’ve designed, managed, and procured dozens of processes from role to role handoff processes, cross-functional initiatives, manager enablement and playbook creation.

Helping 9-5 pros build their Corporate Offramp | Land 1st client in a 1-person business you control

You’ve outgrown your 9–5. 
Now what? 

You’ve built a solid career. Maybe even a great one. But lately… 

The Sunday scaries hit a little harder.
You keep wondering, “Is this really it?”

You don’t hate your job. You’ve just outgrown it. And the money is the only part that serves you. 

You’ve done everything right.
But you still feel boxed in by meetings, org charts, and the constant anxiety of “restructuring.”

You know your skills are worth more – but no one’s shown you how to turn them into something of your own.

You're not trying to blow up your life.
You just want to know it’s possible.

That’s what the ‘Corporate Offramp’ is for.

It’s my step-by-step system to help high-performing professionals:
→ Package their skills into a client-ready offer
→ Build a simple audience of people ready to work with them
→ Land their first client in 120 days—without quitting their job

You’ll start earning outside your 9–5 and finally take control of what’s next.

This isn’t about quitting tomorrow.
It’s about progress. Building something – before you need it. 
And when you’re ready to start having control over your time. 

What others are saying:

“What really stands out about Brian is his authenticity. And his responsiveness is in a league of its own. His mix of broad entrepreneurial knowledge, specific expertise in areas like LinkedIn strategy, and straight-talking advice puts him at the top of my list.” 
– Melissa, ex-ed tech exec

“I started building while still in my 9-5, and landed my first client within 3 months (..before being let go by my company!).”
– Cassie, former tech manager

Here’s how to get started:

📥 Grab the Free 5-Day Solo Business Blueprint in my Featured section – and get the exact roadmap to land your first client without quitting your job (or even changing your LinkedIn profile). 

🎯 Want a faster path?
Join me for the Fast Track to Freedom Workshop – where I’ll walk you through:

• What to focus on (hint: not your website)
• Where 90% of your effort should go
• How to build an audience (without posting daily)
• The path to your first paid client – in 120 days

🎟 Save your seat: simplemanguide.com/workshop

Your 9–5 got you started.
Your next move is on your terms.

Brian Gallagher

The real risk isn’t leaving your job.

It’s staying just long enough that the comfort…

Becomes overwhelming.

People frame risk as walking away from stability. But stability’s not real. Just ask the people who thought they were ‘safe’ at Amazon or Microsoft.

The real danger is slower. Quieter.

You start caring a little less. You’re no longer motivated by what you're doing. You move through your days on autopilot.

You get lulled into sleep. Unsure what even makes you feel alive anymore.

You let people steal your time with fake urgency and pointless meetings.
You tell yourself you’ll make a move when things calm down.

But that moment never comes.

I remember when it started happening to me. The pay got better. The hours eased up.

On paper, everything looked fine.

But I didn’t like what the years ahead looked like.

I watched people higher up the ladder still asking permission for the simple things — a doctor’s appointment, a softball game, a random Tuesday.

And I knew if I didn’t draw a line, I might never draw one. I’d wait for the next bonus. Then the next. Then the next.

And 20 years later, I’d be so deep in it that walking away would feel impossible.

That’s how comfort works.
It feels just good enough that you stop questioning it.

Comfort doesn’t just keep you in the job.
It keeps you from becoming the person who’d ever leave it.

It’s a slow slide toward a life you never chose.

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In my last role, I was a VP in investment banking.

On paper? Looked great. But in real life… 

Yikes.

I’ll admit – the instant status it gave me when I told people what I did made me feel important. 

But I was constantly stressed. 

If I wasn’t at the office, I was dreading the next email ping from a managing director. 

Why? Because I had no visibility as to how my week would look. 

One minute I had a long weekend train trip planned. And an email ping could mean having to cancel everything. 

Honestly, it was chaos. 
But I kept telling myself it was “worth it.” 

Everyone seemed impressed with my title, so I was on the right path. That’s what I thought. 

Eventually I caved and said yes to something different. 

I started a fitness studio concept with a friend (while still at my job). 

Just a few classes a week. Nothing fancy.
But it was ours. We made the calls.

It didn’t make me rich. And unfortunately, it didn’t become my forever thing. 

But besides being the most fun I’ve ever had ‘working’, it did something else for me: 

It broke the cycle.

And once I got a taste of calling my own shots,
I couldn’t go back.

Now I help other people build something of their own too.

Because I’ve experienced both sides: 

Waking up dreading the work day. 
Waking up excited about what I get to build. 

And know I’m certain on which I’ll keep choosing.

I did a breathwork session last week.
Two words kept repeating.
And they stayed with me all week.

Kindness.
Vulnerability.

Two simple words. But they are the difference between forcing connection and creating real connection.

Kindness reminded me that everyone I talk to is carrying something I cannot see.

Clients. Prospects. Friends. Family members.
People on here scrolling through their day.

When I remember that, I show up better. My coaching is better. My conversations are better. My patience is better.

Vulnerability reminded me that the people I trust most are the ones who let me see the full picture.

Not the “everything is amazing” picture.
The human one.

So I am choosing to bring more of that into how I show up here.

And I will start today.

I am going through a breakup.

It has been difficult, but being around family, and keeping my schedule full, helps.
Movement helps. And so does work.

And during that breathwork session, something small set me off, and I realized how much I had been holding.

And yes, for a bit, I pulled back on some things while I got my footing again (work included).

But this experience is giving me something important.

A deeper appreciation for how much our personal lives shape the way we show up in our work.

A deeper understanding of what my clients feel when they are trying to build something while holding the rest of their life together.

And a deeper commitment to lead with kindness and vulnerability in every part of my life. Not just my business.

I want the people who follow my work to feel that they are seen, not judged.

And I want them to know that building a solo business is not separate from real life. It happens inside real life.

Work does not happen in a vacuum. Life does not pause while you build something meaningful. 

Who you are matters just as much (if not more) as what you do.

That breathwork session reminded me of that.

And it marked a change how I plan to show up here moving forward.

My brother’s dog, Norman, always helps too :)

“It’s been four months and I still feel stuck.”
Someone told me this the other day.
Here’s what many underestimate when starting out: 

Just how easy it is to waste time trying to figure everything out on your own. 

And when building while still employed, it’s not helpful to see 15 different paths. All promising places to start, but unsure as to which is most viable. Which leads to revenue fastest. Which has the least speed bumps. 

So what do I see most people do? 

Dabble. Start researching. Build a website. 
Try one thing, then second-guess themselves and switch. 

And four months go by. Then six. Then a year. 

And somewhere quietly in the background, they’re thinking:
“I thought I’d be further along by now.”

Time spent stuck doesn’t just slow you down.
It starts to convince you maybe you weren’t meant for this.

You can figure it out alone. Lots of people do. 
But it usually takes them 18–24 months of guessing, circling, rebuilding, and trying to reverse-engineer the right sequence.

Or…

You get help. You get a map. You talk to someone who’s already walked the road.
And you collapse that timeline down to a fraction of what it would’ve been.

Some of my clients have signed their first client in less time than most people spend thinking about how to start.

Most people don’t fail.
They just run out of time and energy they didn’t know they were burning.

So if you’re four months in and still stuck, nothing’s wrong with you.

You’re most likely trying to navigate a process in the dark that someone could’ve lit up in a single conversation.

The question is no longer:

Can you do it alone?

It’s:

How much is the extra 12–18 months worth to you?

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The Battle

Matt Schalsey

Brian Gallagher

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The Battle

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Brian Gallagher

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Engagements

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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);}Brian Gallagher's LinkedIn Performance

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