I help companies see around corners as they adopt next-generation technology..navigating compliance, accelerating digital transformation, and driving operational efficiency.

With a track record in SaaS sales, I’ve consistently won net-new logos and delivered double-digit ARR growth by helping mid-market and enterprise clients modernize with Cloud, AI, and IT solutions.

I execute with precision through pipeline discipline, value-based selling, and a relentless focus on customer success and measurable impact.

Above all, I lead with sincerity, believing that how we work matters as much as what we build.


Alexandrea S.

Word of advice: don’t ever take your foot off the gas

Alexandrea Stewart

I’m a Sr. Acquisition Account Executive at Pluralsight, helping organizations upskill their technical teams and close critical skill gaps in an ever-changing tech landscape.

My background is rooted in SaaS sales, where I’ve spent my career learning how to run strong discovery, build real business cases, and create value for customers—not just sell software. Prior to Pluralsight, I spent nearly four years at Udemy, where I was a top performer and earned three promotions by consistently focusing on customer outcomes, discipline, and adaptability.

I’m especially passionate about sales craft—discovery, outbound strategy, deal qualification, and career development for AEs. I believe great sellers win by being curious, prepared, and intentional, not by chasing every deal or relying on volume alone.

Outside of day-to-day selling, I enjoy sharing lessons learned, wins, losses, and real talk about sales on LinkedIn. Always open to connecting with others who care about improving their craft and building meaningful careers.

Mike Jacovsky

The job market is no joke right now.

I get at least a couple messages every week from people asking about roles, the market, or just what I’m seeing out there. 

It’s a good reminder of how many solid people are trying to navigate the same thing.

One thing that I just keep thinking to myself: your network matters, a lot.

Your network can only help if you’ve actually taken the time to build it up.

That’s why I think we’ll see a shift this year in how people use LinkedIn. 

Less posting just to post, more real conversations, more messages, more relationship-building on here.

Enabling Enterprise Technical Teams to Upskill, Reskill & Drive Measurable Impact | Pluralsight

I love being fully remote, zero complaints, but I do randomly miss the office moments where a coworker would walk up and go, “Hey, want to go for a walk?”

Fast forward 40 minutes…

You’ve walked two miles, talked about everything except work, and suddenly realized you were supposed to be back at your desk 30 minutes ago.. (don't even bother looking at those where are you slacks)

No meeting, no agendas, just accidental cardio and good conversations.

There are a lot of great sellers, people, and voices on LinkedIn. No doubt about it.

One thing I always try to remind myself though: we don’t all work in the same industries.

A post can sound amazing - the messaging can be sharp, the results can look impressive, but sometimes what you’re reading works really well for their niche & not necessarily yours.

I don’t think the goal is to copy and paste what others are doing to win deals or boost reply rates. 

The actual value here is using their ideas as guideposts, then tailoring them to your industry, your buyers, and your day-to-day reality.

That part takes more work, yes, but at the end of the day you know your customers or at least you should...

You know their language, you know what resonates, and what doesn’t.

Borrow the ideas & customize the execution.

Quick reminder to take care of your mental health - I talked about getting a massage a few weeks back, well another one for me is being on the water.

For me, getting on the water is a reset. Kayaking clears my head, slows things down, and helps me recharge before jumping back into work - especially needed after a few days of intense learning at our RKO.

It’s easy to skip this stuff when things get busy, but I’ve learned I’m better at my job when I make time for it.

Find what refuels you and don’t feel guilty about it.

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If you stop learning, you can pretty much say that you're giving up on growing.

Earlier today I joined a webinar where 🏄🏼‍♂️ Scott Leese Leese played the role of a prospect while an AE ran a live demo. 

Afterward, Scott gave direct feedback in front of everyone.

First off, huge kudos to the people who volunteered. That’s not easy to do in front of a large group, especially with people you don’t know watching. Every one of them did a solid job.

What really stood out to me was why they put themselves in that position.

They showed up to learn.
They showed up to grow.
They wanted more for themselves.

Putting yourself out there, asking for feedback, and being open to criticism, especially from someone like Scott is how real growth happens.

I like to believe that comfort doesn’t create progress, learning does.

The people willing to lean into that will always separate themselves.

One thing I’ve noticed that really separates reps right now?

They do the extra prep, I'm talking 30 minutes of real research about what the company.

In a market this competitive, taking a little time to research the company and the person you’re meeting with goes a long way. 

And with Ai, it’s honestly easier than ever to build out a few talking points.

The reps who do it show up sounding informed, asking better questions, and having conversations that actually feel relevant & not scripted.

That effort stands out fast, especially when most people don’t bother.

One thing I’ve learned over time: a Sunday reset makes a big difference.

When I worked in car sales years ago, I used to get a massage every Sunday to reset before the week. 

I stopped for a long while… and recently started doing it again now that I'm at Pluralsight. 

The difference on Mondays has been huge so far.

I feel like I have more energy, a clear head, and I don't feel like I'm dragging myself into the week.

It’s a small investment, but starting the week strong changes everything. 

A slow Monday can mess up momentum fast.

Find your reset, whatever it is, it’s worth it.

Two days into Pluralsight's RKO (SKO), and one thing has really stood out to me - there are some incredibly smart, capable, and talented people at this company.

The reality is, most companies have people like that - but you don’t always get the chance to actually learn from them. 

Day to day, everyone’s busy - different teams, different time zones, different priorities.

That’s what makes time like this so valuable.

Being able to sit in the room, listen to how others pitch, how they ask questions, how they think through strategy and run their deals - that’s where a lot of the real learning happens.

When you’re surrounded by that much talent, there’s no shortage of ideas you can take back and put to use right away.

Attention is the hardest thing to earn in sales right now.

Prospects have more options than ever, more competitors, more noise, and it’s easier than ever for them to go with someone else if you don’t stand out quickly.

That’s why building value fast matters.

You don’t have multiple calls to “warm them up.” 

You get a small window to show you understand their world, their problems, and why talking to you is worth their time.

If you can’t capture their attention early, the deal drifts, someone else steps in, and you’re left wondering what happened. 

I won't even get into how you have to explain closing the opp to your manager after forecasting that deal in your pipe a few days ago...

If you want to stay in the game, build value quick by doing your research beforehand.

One thing I see sellers do all the time, and yes i'm still guilty of doing this myself from time to time is - they hear a “no” and immediately try to overcome it.

The problem? They don’t actually understand what the no means yet.

A prospect can say no for a lot of reasons:
- Bad timing
- No budget (right now)
- They’re happy with a current vendor
- They don’t fully understand the value yet
- They’re just trying to end the conversation

All of those sound like “no”… but they’re very different situations.

If you jump ahead too fast, you risk pushing back on the wrong thing or worse pushing yourself out of the deal entirely.

Once you slow down and understand the real no, you can decide:
- Is this worth digging into?
- Is there something to reframe or clarify?
- Or is it actually time to walk away?

Not every no deserves a fight, but the right ones deserve the right pushback and that really only happens when you truly understand what’s behind it.

taplio

The Battle

Alexandrea S.

Mike Jacovsky

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taplio

The Battle

Alexandrea S.

Mike Jacovsky

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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);}Alexandrea S.'s LinkedIn Performance

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