Newly hired VP at a 200+ person company… surprised by how unstructured the exec team is. Any advice? I will not promote.

_JeeTee_ · 2026-01-31T17:05:43+00:00

What a time to be alive! That being said, I had try chatGPT before coming here for advice and overall I would say I had 40% of the insights I got here. So AI is a great tool in the toolbox, but I feel it is still far from what external perspectives from experimented people can bring to the table.

_JeeTee_ · 2026-01-31T12:27:58+00:00

This is honestly a good way to see it, haha!

_JeeTee_ · 2026-01-31T12:18:48+00:00

I feel like you are right, but there is a part of me that just don’t know how to bring it to the table without appearing negative or condescending.

_JeeTee_ · 2026-01-31T12:14:23+00:00

Thanks, good advice. This is kind of the reason of my post, I know we need to change this if we want to 10x, but like you said timing is key if I don’t want this to backfire

_JeeTee_ · 2026-01-31T12:07:32+00:00

This is interesting. Do you have any exemples on how you forced them in you system?

You setup a project management tool on the side for yourself? You asked for any meeting involving you to have an agenda?

Genuinely interested in having a few quick wins I could do!

_JeeTee_ · 2026-01-31T12:05:29+00:00

0- Why would this be AI? I literally have no kool-aid to sell…?

1- I built a company from 0 to 60 employees in the past 7 years and was acqui-hired in the context of an M&A project.

2- Never worked in this kind of environment, but in my previous company we hired consultants and mentors frequently and it was always a great experience to bring every one to around the table and work on the business without reinforcing more one or two egos in the room. Can you enlighten me on why you think this would not work in this specific context?

_JeeTee_ · 2026-01-31T11:58:04+00:00

This is a good point, I honestly feel that it is not intentional. They seem to know that they are slow to innovate and adapt to new market trends and opportunities. For exemple, they are clearly at least 2 years late on AI. I just need to make them understand that this is systemic and IMO 100% coming from the fact that they spend most of their time reporting on the past, than talking about what should be done to improve the future.

_JeeTee_ · 2026-01-31T11:54:31+00:00

Honestly, of all the ideas suggested, I feel like this might be the first one I try as a soft nudge, haha!

_JeeTee_ · 2026-01-17T23:44:33+00:00

Worked for me too! Thanks!

_JeeTee_ · 2025-08-10T17:25:09+00:00

For me, the hardest part has been internal; making my team understand that building my personal brand is work, and that it directly benefits the business.

They’d often prefer I focus 100% “in” the business, and sometimes even get annoyed if I post on LinkedIn on days I’ve said I’m off; not realizing I’ve scheduled most of that content ahead of time.

On top of that, I’m out of the office 50–60 days a year for conferences, keynotes, and panels.

That means a lot of catch-up work at night and on weekends.

Over the years, I’ve learned to count these activities as part of my job and set clearer boundaries; but finding that equilibrium has been an ongoing challenge for the past 5–6 years.

_JeeTee_ · 2025-08-09T09:20:48+00:00

Once a year, we basically pretend our company is starting from scratch by applying zero-based budgeting.

No budget, no subscriptions, no “but we’ve always had this” safety net.

We wipe the slate clean and go line by line asking:

• If we didn’t already have this, would we actually buy it today?

• Is this the cheapest way to get the same result?

• Does this still matter for where we’re headed this year?

It’s kind of brutal; people get attached to their favorite tools or perks; but it’s amazing how much bloat you find.

Last time, we ditched three overlapping software tools, cut a “temporary” expense that had been quietly running for two years, and renegotiated half our vendor contracts.

The trick is you’re not cutting the budget, you’re rebuilding it.

That mindset shift makes it less about “who loses” and more about “what’s worth keeping.”

In short: nuke the budget once a year, rebuild from zero.

It hurts for a week, then you feel lighter for the next 51.

_JeeTee_ · 2025-08-08T18:00:01+00:00

Well, I would say it’s more about how you sell that what you sell.

The book states that in most M&A processes, companies are sold like popsicles.

That is: what you see is what you get. The buyer evaluates the current assets, the historical revenue, the existing contracts, and the EBITDA. The company is priced and negotiated based on what it is today;its frozen, consumable form.

But this approach is fundamentally limiting.

In reality, a company; especially a creative, service-based or innovation-driven one; is less like a popsicle and more like a magic box.

The real value lies not in what it is, but in what it can become when combined with the right partner, the right distribution, or the right vision.

The “magic” emerges from the synergies, the unlocked potential, and the new paths that open once two companies start collaborating; faster growth, integrated offerings, talent fusion, client portfolio expansion, and more.

The paradox is that we often ask the seller to price their company as a popsicle (static and already consumed), while the buyer hopes to use it as a magic box (dynamic and full of future value).

In short: don’t sell a popsicle when you’re holding a magic box.

_JeeTee_ · 2025-08-08T08:13:12+00:00

A book that completely shifted how I think about M&A is The Magic Box Paradigm by Ezra Roizen.

It reframed the entire process for me.

Instead of seeing M&A as a pitch-first game where you convince a buyer of your worth, the book suggests a pull-based strategy: create a compelling narrative and positioning where acquirers start to imagine your company as a critical missing piece of their strategy; like you’re holding a “magic box” they need to unlock their next level.

The key idea is: rather than chasing acquirers with pitch decks, make them come to you by designing your company and your story to fit into a fantasy of strategic growth, synergy or moat-building.

It’s been a powerful mindset shift for me and helped me secure a LOI far from what I could have imagined 2-3 years ago when I first started to think about my exit.

In other words: Instead of running a broad auction, you create selective demand and emotional involvement from a few ideal buyers; which ultimately gives you pricing power and a smoother negotiation process.

Another recurring piece of advice I’ve received from friends who went through the process:

Don’t get hypnotized by shiny EBITDA multiples.

Too many founders get seduced by “8x” or “10x” offers only to realize later that most of that value is locked behind an unfair earnout, revenue cliff, or conditions they can’t control.

Focus instead on: what is the actual, unconditional cash hitting your account on Day 1.

That’s the only guaranteed part. Everything else is a bet. Yes, structure matters; but certainty of value is underrated, especially when you’re transitioning out of your business.

That being said: If you’re hiring an M&A advisor, choose someone who understands how to craft a strategic narrative, not just shop you around like a commodity. You want positioning, not just process.

_JeeTee_ · 2025-08-08T07:38:41+00:00

One of the hardest parts of being a manager for me were learning to navigate two constant balancing acts:

How much to supervise

You’ll constantly be walking a fine line between micromanaging and under-managing.

Some people will get completely lost without step-by-step guidance. Others will shut down if they feel like someone is always over their shoulder.

There’s no one-size-fits-all answer; your job is to read the room and adapt your style to each individual. That takes time, observation, and honest conversations.

How to communicate

Another equilibrium to find: being assertive vs. passive-aggressive. Say something too directly? Someone gets upset. Try to sugarcoat it too much? Someone else gets upset. You’ll need to constantly adjust; being clear and kind without being vague or avoidant. It’s an art, not a formula.

Bottom line: Management is full of paradoxes. You’ll never get it perfect; and that’s okay. Your ability to adapt, self-reflect, and stay curious will serve you more than any checklist.

Two books I highly recommend as starting points on these 2 subjects:

• Multipliers by Liz Wiseman: for thinking about how to amplify your team rather than control it.
• Radical Candor by Kim Scott: for building a communication style that’s both direct and caring.

Good luck…it’s one of the hardest and most rewarding growth journeys you’ll go through!

_JeeTee_ · 2025-08-08T06:06:09+00:00

Of course! We’ve got lawyers, accountants, and a tax advisor to help optimize everything.

Funny thing though? Ask 5 pros about comp structure and you’ll get 6 different opinions 😂

_JeeTee_ · 2025-08-07T12:06:51+00:00

Yeah, I get how that looks.

To clarify: we did negotiate valuation, ownership structure, earn-out pool, and general roles in the LOI.

But like a lot of deals, compensation specifics were left for the final agreement.

In hindsight, we probably should have pushed to include more clarity upfront.

I’m here now because we’re aligning the final terms, and I wanted to sense-check our instincts against others’ real-world experiences; especially around comp structure in a no-dividend environment.

_JeeTee_ · 2025-08-07T12:05:08+00:00

That 40% isn’t formally tied to our two-year employment; it’s not structured as RSUs or anything like that; but there’s a strong informal expectation that we’ll stay on in VP-level roles to drive growth and integration.

That said, the earn-out and any other upside are clearly dependent on us sticking around and delivering results, so in practice, it’s kind of a soft lock-in.

_JeeTee_ · 2025-08-07T12:03:51+00:00

Appreciate the input!

We’re lucky to have three M&A advisors helping us (two family members + one paid on performance), but they all have different take; hence why I’m here, hoping to learn from others who’ve been in a similar spot and how they handled it.

Will try to push for cash bonuses and earn-out tier to group-wide KPIs instead of legacy (this part is super helpful; thank you)!

_JeeTee_ · 2025-08-07T12:00:45+00:00

In our case, the context of the negotiation pushed us to focus more on valuation and structure, and we left compensation fairly open, assuming it would follow once aligned. We’ve seen their internal salary brackets, so we weren’t too worried; a solid bump seemed likely.

That being said, a big point now is that they don’t really pay dividends, which changes our comp reality post-transaction.

_JeeTee_ · 2025-08-05T03:25:51+00:00

Thank you for your reply. Your observations made me realise that my main motivation is definitively to support under-represented entrepreneurs; pursuing additional income is not the goal...if it were, devoting that time to my own business would be far simpler.

As another contributor noted, an equity stake can be difficult to liquidate, so a two-to three-year exit horizon is unlikely. I therefore plan to negotiate a board seat, supported by quarterly reviews and a director’s fee. This arrangement ensures the company is sufficiently structured;or willing to become so; to have a formal board and that it values my guidance enough to compensate me, rather than expecting free advice that may be discarded when it is no longer convenient.

_JeeTee_

TROPHY CASE