Jake Wolpert

The ISH

I specialize in helping early-stage startups and growing companies set the foundation for scalable revenue by ensuring their initial sales hire is set up for success. My work focuses on aligning go-to-market strategy with talent acquisition, onboarding, and early sales process design.

Here are the key areas I support:

*Defining the ideal profile for a first sales hire 
*Structuring the hiring process to attract and close top talent
*Designing onboarding plans that drive quick time-to-impact
*Building repeatable early sales playbooks and pipeline strategies
*Coaching founders and first reps through early-stage sales challenges

Founder

I help people in two situations: those wanting to escape corporate and build their own thing, and successful solopreneurs who feel trapped by their own success.

For corporate professionals ready to make the leap: You're successful but restless. Good job, decent money, but Sunday nights feel heavy and you keep thinking "Is this it for the next 20 years?" I help you build your exit strategy while you're still employed - no reckless quitting, just systematic planning.

For established solopreneurs: You've built something profitable but you're working 60+ hours a week. You need systems that let the business run without your constant oversight. I focus on the practical stuff: prioritization frameworks, systematization strategies, and preparing for scale.

My approach is direct and actionable. No vision boards or "find your passion" sessions. Just frameworks, accountability, and strategies that work in the real world.

Currently developing a comprehensive program for corporate professionals looking to transition to independent work.

Coach

Shalion

Developed and led the agency GTM motion as we attempted to break into North America

Vice President of Global Agency Sales

Intentwise

Vice President of Sales

Advisor & Fractional VP of Sales

Acquco

Head Of Sales

Blue Wheel Media

Director of Sales

Feedvisor

Director of Enterprise Sales

Sales Manager

Senior Account Executive

Rutgers Business School

MBA Student

Chief Executive Network

Director of Sales 

Sales Leader @ Shalion

I was put on this planet to empower people. I believe you put people first and everything else second. 
That’s what leadership is about and I’m really good at it. Over the last decade I’ve built lean sales teams where people feel good and do their best work. The results always follow but I don’t think about getting the best work out of my team. Instead, I create environments where they bring it out of themselves.

Reach out to me if you need help in any of the following areas:

-Making your initial sales hire

-Creating sales process and infrastructure for your next stage of growth

-Looking to become a solopreneur or get clarity on your next strategic move

Two identical VP of Sales offers. Same salary. Same equity. Same title.

Company A: $2M ARR, burning $400K/month, $3M in the bank, 15% monthly growth

Company B: $2M ARR, burning $150K/month, $8M in the bank, 8% monthly growth

Which one do you take?

In my experience, most senior leaders don't know how to evaluate these numbers. No one teaches this stuff. You learn it the hard way.

Trust me, I've learned it the hard way. Multiple times. When they say "we're building a rocket ship," make sure to ask how much fuel is in the tank.

I've seen too many talented people (including past me) get excited about a title and equity without asking the questions that actually matter. Then six months later they're blindsided by layoffs or watching the company slowly die.

Here's what to watch out for:

How long can they actually survive? Company A has less than 8 months of runway. You could be walking into a role where fundraising pressure dominates every decision. Miss a quarter and suddenly you're managing layoffs instead of building a team. Company B? Over 4 years of breathing room. That's the difference between desperation and strategy.

What's the growth actually costing them? Company A is growing faster but burning 3x more cash to get there. Are they building something real or just buying revenue they can't sustain? You need to know if you're joining a rocket ship or a house of cards.

Are customers actually sticking around? A company can show you $5M ARR all day long. But what if they're hemorrhaging 10% of customers monthly? You're inheriting a retention crisis, not a growth opportunity. Are you building on a foundation or constantly replacing what's breaking?

And I get it. This information is not always easy to get. It’s uncomfortable asking these questions but if a startup won't share these metrics with a VP-level hire, that's your answer right there.

If you're betting your career on their vision the least they can do is show you the scoreboard.

Founder @ The Initial Sales Hire | Big goals for 2025! | Empowering the Next Wave of Solopreneurs

You might see me in your feed pretty often but I'd consider myself a behind the scenes guy.

DMs. Texts. Quick calls. Coffees. FaceTimes for a select few. Commenting on other people's stuff. Reaching out with no agenda.

That's where the real work happens. Intentional, but not transactional. You do the work without keeping score and let the wins find you.

There's no dashboard for this. No way to track which text, which coffee, which comment ends up being the one. Might pay off tomorrow. Might take years. You just trust the work compounds.

The proof is in two of my most exciting opportunities right now. One came from a random conversation at my gym. The other from someone I worked with 8 years ago, for four months, on different continents. Talk about a slow play.

My business partner? Met her on LinkedIn after trading DMs a year ago.

None of this was strategic. But all of it compounded.

Show up. Stay curious. Don't be weird about keeping in touch.

The math doesn't make sense until suddenly it does.

Be careful hiring someone you know for your first hire.

I know that sounds backwards. Everyone says "hire people you've worked with, you already know they're great!"

Except... you know they were great THERE. You have no idea if they'll be great HERE.

This is how it goes:

You worked with someone who absolutely crushed it. So naturally you think: "They were amazing. I should hire them." (Seems logical, right?)

But you're not asking the right question: What environment made them amazing?

Maybe they thrived because of:

- Clear structure and processes
- Resources and support teams
- Established playbooks

And your business has:

- No documented processes yet (you're winging it)
- Limited resources (it's just you)
- You're building (in your brain) as you go 

Be careful assuming past success automatically translates.

That person who was incredible at their last company might be incredible BECAUSE of that specific setup. Change the conditions, change the results.

Before you hire someone based on past success, ask: "What made them successful THERE, and do I actually have those same conditions HERE?"

If the answer is no, you're setting both of you up to fail. (And could be torpedoing a friendship in the process.)

Your prospects have no idea what you're talking about.

Not because they're stupid. Because you have information they don't.

Here's a quick test:

Pick a well known song. Hum it or tap the beat on your desk. Ask someone to guess it.

They won't get it. Even though it's obvious to you.

Know why? Because while you're humming, you're also hearing the full song in your head. The lyrics, the instruments, everything. You have perfect information.

The other person just hears tapping.

This is exactly what happens in sales.

You pitch your product. You know what you're trying to convey. You understand the impact, the value, the ROI. It's so clear to you.

Meanwhile your prospect just hears tapping.

They don't have your training. They don't have your experience with the product. They haven't seen it solve the same problem fifty times.

Stop assuming you're on the same page. You're not.

Slow down. Check for understanding. Ask questions. Make sure they're hearing the full song, not just the tapping.

This applies outside of sales too. Anytime you're trying to explain something that's crystal clear in your head, remember: the other person is only hearing what you're saying, not what you're thinking.

Adjust your perspective. Close the information gap.

That's when things actually click.

To everyone who's subscribed to LaunchIT! Labs so far, thank you!

To everyone else… whatever.

But seriously, the replies we've been getting have been incredible. People sharing what resonated, asking real questions, telling us "this is exactly what I needed to hear right now."

That's the stuff that makes this worth doing.

When Nikki and I started this newsletter, I wasn’t sure if our style would translate (luckily, Nikki did). We're not polished. We don't follow the typical business newsletter playbook. We just wanted to share what's actually worked for us, give you tactical stuff you can use, and challenge you to think deeper about what you're building.

And while we’re just getting started, it feels like we’re on the right track.

Engagement rates are high. We're adding new subscribers every day, and honestly it's been wild to watch. If you haven’t already, subscribe now and you'll get the first two newsletters right away, plus everything we've got coming.

To everyone already in, seriously, thank you. Your engagement is what makes this fun.

If you weren't touching base with me before the holidays, don't try touching my bases after the holidays…


Just kidding, please call me in January.

Having an emerging coaching business was not something I necessarily planned. I kinda stumbled into it, which is probably why it's working.

I didn't get certified. I didn't read books on how to be a coach. I didn't create a framework first and then go find clients to fit into it.

People kept reaching out because they were facing decisions I'd already navigated. And I started helping them using the only thing I had: real experience from actually doing it.

Turns out, not having a "coaching playbook" is my biggest advantage.

Most coaches learn how to coach and then find people to coach. I lived the thing my clients are trying to do, then started helping others navigate it. There's a massive difference.

I'm not a life coach. I'm not going to ask you about your childhood or tell you to journal about your feelings (these things are important though).

My clients are high achievers at major inflection points who need more than just motivation and encouragement. Yes, I'll support you. But you also need someone who will challenge your thinking, push you to think bigger, and call out the limiting beliefs that are actually holding you back.

ISH is still going strong. But if you're wrestling with a major career or business decision and want to work through it with someone who's been there, message me. I have two spots open for December.

I just helped a client make their first hire. We didn't talk to a single candidate for almost a month.

Felt slow. Probably looked slow from the outside too.

But here's what most founders do: Feel the pain of a gap on the team, panic, post a job that afternoon, start interviewing the next week. They're moving fast. It feels productive. (Look at this interest!)

Three months later they're still "seeing candidates." Or worse, they settle for someone out of exhaustion and they're gone in 90 days.

That's the hare. Feels fast but finishes slow.

We were the tortoise.

We used that time to get clear on what we were actually looking for. Not just a job description, the real stuff. What does this person do every day? What does success look like over the first few months? What kind of person thrives here? What do the first two weeks look like so they're not just figuring it out on their own?

By the time we started interviewing, we knew exactly who we wanted AND how we'd set them up to win.

The process was smooth. Didn’t go through a ton of candidates and the interviews were efficient.

The tortoise can feel like nothing is happening. Until suddenly everything happens all at once.

Slow and intentional still wins. Even in hiring.

To the BDR who's been grinding and hitting quota for the last year:

You're more powerful than you think. And I don't mean that in a motivational poster kind of way.

You've sent thousands of emails and made thousands of calls. You know which messaging gets replies and which gets ignored. You know what titles are worth targeting. You've heard every objection before a deal even starts. You are the first to hear about new competitors. You know why prospects ghost.

You have information that marketing, sales leadership, and product are all trying to figure out separately. Meanwhile they're scheduling cross-functional syncs and building dashboards. You just... know.

But you're not thinking about that. You're thinking about hitting your number and getting promoted to AE.

I get it. That's the path everyone talks about.

There’s nothing wrong with that but AE is one option. It's not the only option.

You could move into product marketing because you already know what messaging lands. Sales enablement because you can teach what actually gets responses. Marketing ops because you understand the funnel better than the people building it. Customer success because you know what's being promised before the deal even closes. RevOps because you've lived inside the systems everyone else just reports on.

Or you take everything you've learned and go somewhere else where that expertise is even more valuable.

Most BDRs think they just book meetings. Meanwhile, they’re learning how their company's product lands in the market with real buyers. That context is irreplaceable.

We're in an expertise economy. And BDRs are sitting on more of it than they realize.

"I'll just do it myself."

Every founder says this at some point. Usually multiple times a day. Can also sound like:

“Ok just send it to me and I’ll finish it.”

“I want to look it over before sending it out.”

We all get it. You CAN do it faster. You WILL do it better. Training someone else feels like it takes forever when you could just knock it out in 20 minutes.

But think about what's really happening when you say that:

It's not about speed. It's about control.

You don't trust someone else to do it the way you would. You don't trust them to care as much. You don't trust them to get it right.

So you do it yourself. Again. And again. And again.

And now you're the bottleneck.

Every decision runs through you. Every task waits for you. Your business can only move as fast as you can personally execute.

Congrats, you've built a company that can't function without you.

Keep in mind, every time you say "I'll just do it myself," you're choosing short term efficiency over long term leverage. You're trading the 30 minutes it would take to teach someone for the hundreds of hours you'll spend doing it yourself forever.

You're not building a business. You're buying yourself a job that never ends.

The real question isn't, "Can I do this faster myself?"

The real question is: "What am I NOT doing because I'm busy doing this?"

Because while you're handling tasks that someone else could learn, you're NOT:

- Building strategy
- Developing your team
- Working on the business

"I'll just do it myself" feels productive but I promise you it’s not.

This is a hell of an opportunity. And even if you're not ready to make a move right now, I'd start following Isaiah Crossman and the Repeatability team.

Partner @ Repeatability (former CRO @ Tropic & Strategic AE @ Wunderkind)

Things are going so well at Repeatability that we’re hiring yet *another* person. Perfect role for a BDR, early career AE, or anyone smart & ambitious (read my pitch to you below…)

Most companies suck to work for.

Most managers are useless.

Most products suck to sell.

And yet people bounce from job to job every couple years (at best) over and over again, hoping something will change.

Woof.


Perhaps our most important guiding principle at Repeatability is to build a company so good that we can all work here for the next ten years (maybe longer).

Basically, we’re building the company we’ve all always wanted to work for.

For example, we own the business outright. We’re profitable. Salaries are paid by the revenue from our customers, that’s it.

And it’s just plain fun to work here.

For example, our team meetings are hilarious (and only half business). You can easily validate with any of the five of us (Elsie, Hayley, Brooke, Luke, or me).

And perhaps most importantly, there’s nothing better than being on a winning team. We’re absolutely killing it for our customers (hence hiring for our own team…). And I don’t mean this obnoxiously at all, but we have a *very* talented team (exactly who any top performer should want to surround themselves with).


Yes, you’d be making a career change to recruiting (or perhaps you're already a recruiter?).

And depending on what you’re doing now, you might take a short term comp hit, but long term I believe (1) you’ll be way happier and (2) you’ll end up making way more.

Comp is at least $100k (some flexibility depending on seniority etc… if you think you’re the right person, don’t let this be a reason to not at least chat with us).


Recruiting is awesome. It’s just another form of sales.

But the “product” is consistently amazing (we’re helping very talented and/or high potential folks find high paying jobs at the best startups)...

The biggest reason to not chat with us would be if you can’t commit to 9-10 productive, focused hours during the week. Nothing required on weekends.

That said, we do also take care of ourselves (for example, we’re shutting the company down for a week and a half around new years).


‼️ If this piques your interest (OR if you know someone), please do hit me up. I’d love to chat with you.

And if not, anything you can do to help get this post in front of a ton of people would be v appreciated 🙏

taplio

Jake Wolpert's Linkedin Analytics

Jake Wolpert

Performance ScoreJake Wolpert's LinkedIn Performance

What is Jake talking about?

Jake Wolpert's Best Posts (last 30 days)

Ready to grow your LinkedIn presence?

taplio

.css-6ytdur{background-image:linear-gradient(284deg, rgba(39, 43, 72, 1) 0%, rgba(33, 47, 183, 1) 100%);color:transparent;-webkit-background-clip:text;background-clip:text;}Jake Wolpert's Linkedin Analytics

Jake Wolpert

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);}Jake Wolpert's LinkedIn Performance

What is Jake talking about?

Jake Wolpert's Best Posts .css-1emoo84{font-size:var(--chakra-fontSizes-md);font-weight:400;color:var(--chakra-colors-gray-600);}(last 30 days)

Ready to grow your LinkedIn presence?

Jake Wolpert's Linkedin Analytics

Performance ScoreJake Wolpert's LinkedIn Performance

Jake Wolpert's Best Posts (last 30 days)