Founder Helping You Grow | Follow for Daily Leadership & Growth Insights | Serial Entrepreneur | Ex-RBC

Most $1M-$50M B2B companies hit the same wall: what got you here won't get you there.

Your sales team follows five different versions of your "standard" process. Marketing and sales operate in silos. You're building with borrowed tools and broken playbooks. The same cold email sequences everyone uses. The same CRMs with data nobody trusts.

I help revenue leaders build systems that actually scale.

WHAT MAKES MY APPROACH DIFFERENT

My story isn't typical - at 23, as a single dad, I took an unexpected turn into corporate. In big companies like RBC and Mackenzie, I led teams from 2 to 550 people, learning about product development and large-scale expansion. But I constantly wondered: "Am I too late to start my own business?"

That internal struggle led me to leave corporate safety and build two startups in seven years - eventually exiting basix.ai, a sales automation platform backed by Forum Ventures. That experience taught me something critical: the gap between theory and execution is where most scaling companies die.

Now I bridge three worlds:
→ Corporate operations experience (scaled systems at Fortune 500 level)
→ Entrepreneurial experience (built and exited SaaS company)  
→ Technical automation expertise (hands-on with Clay, Make.com, n8n, HubSpot)

WHAT I'VE HELPED CLIENTS ACHIEVE

→ Generated 9-figure revenue growth for clients and employers
→ Scaled bootstrapped businesses to 7 and 8-figure heights
→ Built full TAM in Clay for enterprise outbound teams
→ Developed GTM playbooks that get used (not filed away)
→ Created systems that let leaders lead again

I don't just provide strategy. I walk the path with you. From Fortune 500 boardrooms to founder-led scrappy startups, I bring operational depth and clarity to every engagement.

MY PHILOSOPHY

Most consultants give you frameworks. I give you forward motion.

I don't chase buzzwords. I build revenue engines, simplify execution, and unlock leadership potential with precision and empathy.

This is not theoretical - it's battle-tested across 10 roles in two companies before venturing out, building two startups, and now advising through Techstars and Predictable Revenue.

If you're stuck in complexity or scaling feels like survival, let's talk about bringing order to chaos and traction to your strategy.

Join 190,000+ founders and operators getting my weekly playbook: https://jaymount.me/newsletter

Connect with me here - I share systems, frameworks, and tactical advice for scaling B2B operations.

Jay Mount

Bridge the Gap. Be Seen. Be Trusted.

I help Boards, CEOs, and ambitious Leaders deliver results their stakeholders can see and trust.

For over 25 years, I’ve advised Leadership Teams and Boards through high-stakes transformations: 
• integrations that stall, 
• platforms that drift, 
• cultures that freeze under politics and fear.

That’s when Leaders and Board members call me. 

They don’t need comfort. They need clarity.
They don’t want jargon. They want results.

And that’s what I have delivered.
• 40% lower operating costs while reigniting growth.
• 15% revenue gains after years of decline.
• Trust rebuilt with regulators and customers.
• Cultures shifted from politics and fear to courage and execution.

Through BRIDGE — my publication — I share the same lens I bring into boardrooms: 
• a way to move from risk to results,
• from vision to proof, 
• from effort to recognition.

👉 Follow me here on LinkedIn for daily posts on leadership, AI, and transformation.

👉 Subscribe to BRIDGE for weekly essays and playbooks – 🔗 bridge[dot]adiagrawal[dot]com

👉 Reach out if your Board or leadership team needs support for oversight, alignment, or coaching that delivers – 📧 mail@adiagrawal.com

Adi Agrawal

Self-doubt at senior levels isn’t random.

It usually follows a pattern:

a quick “good job”
then weeks of silence
then a sharp comment in one meeting
then nothing again

No real feedback.
Just noise.

And noise makes capable people do something predictable:
they start second guessing what others think.

The guessing turns into a story.
The story turns into anxiety.
Anxiety turns into overwork, second-guessing, and smaller decisions.

Not because they are weak.
Because they are operating with unclear standards.

Here’s the fix: upgrade the feedback signal.

Use this 3-question check-in with your boss or key stakeholder:

1/ What do you want more of from me?
2/ What do you want less of from me?
3/ What would make you say, in the next few weeks, “This is working”?

Then ask the question most leaders avoid:

• “When you say ‘strategic,’ what does that mean here?”
• Give me one example of what “good” looks like.
• And one example of what “not good” looks like.

Because adjectives don’t help you improve.
Examples do.
Illustrations do.

One more move that reduces ambiguity fast:

After a high-stakes meeting, send a 4-line recap:

1. What I heard
2. What I’m doing next
3. What I’m not doing
4. The decision I need from you

This isn’t politics.
It’s clarity.

It protects your work.
And it protects your mind.

What’s one vague word you keep hearing –
“strategic,” “more leadership,” “executive presence” –
with no examples attached?

📩 Want more help to strengthen your leadership? DM me
📬 And subscribe https://lnkd.in/gCdavukQ

♻️ Repost to help strong leaders who may be stuck in guesswork
➕ Follow Adi Agrawal | Bridge the Gap

Guide, Whisperer, Advisor to Boards & CEOs | I Help Leaders Deliver Results Stakeholders Can See & Trust | Writer at BRIDGE

If your team is “busy” but nothing moves,
it’s not laziness.

It’s reporting.

Most companies accidentally create
a second job:

Do the work.
Then explain the work.
Then re-explain it.

That second job keeps growing 
until it becomes the real job.

⸻

Status requests don’t just take time.

They change behavior.

People stop writing what’s true.
They start writing what won’t get them in trouble.

That’s how you get:

Long updates
Soft language
Late surprises

⸻

Use a simple test. 

Ask any strong operator:

“How many hours did you spend last week
making other people feel comfortable
about progress?”

If the answer is “a lot,”
you don’t just have a problem.

You have anxiety.

⸻

Fix this with one rule. 

If you want an update, you must ask:

“What decision will this help you make?”

No decision.
No update.

⸻

Replace the weekly status ritual with one note:

What changed
What’s stuck
What we need (and from who)

No deck.
No meeting.

Just the truth
and the asks that unblock work.

⸻

Which update in your org
creates the most reporting
and the least progress?


📩 Want help cutting reporting without losing control? Talk to me.
📬 Subscribe to BRIDGE: https://lnkd.in/gCdavukQ
♻️ If you are a high performer, repost this. Help others.
➕ Follow Adi Agrawal | Bridge the Gap

Most companies don’t have one way of working.

They have two.

The official way.
And the “special case” way.

The second one becomes the “real” company.

Because that’s where things actually get done.

⸻

Every special case creates a hidden system:

A new meeting people don’t know exists
A new approval path nobody can see
A new promise nobody can track

After a while, your team stops asking:

“What’s the process?”

They ask:

“Who do we need to get this through?”

That shift is why execution slows down
even when everyone is working hard.

⸻

Here’s the cost leaders miss:

Special cases make planning impossible.

Your best people can’t estimate
They can’t commit
They can’t protect their time

Because work keeps changing mid-flight.

Not because reality changed.

Because the rules did.

Quietly.

⸻

Do this instead:
Every time someone asks for a special case, ask:

“Are we willing to do this again next month?”

If yes
Change the rule. Make it the new rule.

If no
Don’t approve the exception. Fix what caused it.

⸻

If you want speed, stop adding process.

Remove the hidden system.

Where is the “special case” path
running your company right now?

📩 Want help removing special-case chaos without slowing the business? Talk to me.
📬 Subscribe to BRIDGE: https://lnkd.in/gCdavukQ
♻️ If you are a high performer, repost this. Help others.
➕ Follow Adi Agrawal | Bridge the Gap

The day you stop feeling unsure 😶‍🌫️
is the day you start fading.

Not because you get older.

Because your life got easier.
And your mind stopped doing the heavy lifting 🧠🏋️

Ten years ago, I believed the lie:
Experience keeps me sharp.

Today I’m living the opposite.

This is the most “senior” my résumé has looked.
And I’ve never felt more like a beginner.

Three businesses.
Multiple leadership roles.
New rooms. New bets.
No script.

It should scare me.
But it doesn’t.

Because I can feel the difference:

✅ A week with friction = awake, curious, sharp
⚠️ A week with comfort = dull, impatient, tired

So here’s the Top 10 I’m using to not de-train:

 1/ ⏱️ One hard hour/week. Same day.
 2/ 🔁 One thing you’re bad at. Reps only.
 3/ ❓ One “obvious” question asked out loud.
 4/ 🔄 One new problem type. No autopilot.
 5/ ✍️ One page written from scratch.
 6/ 🗣️ One idea explained in plain words.
 7/ 🧾 One “lost” review (deal/churn/renewal).
 8/ 🎯 One public bet (decision, not a hedge).
 9/ 🪓 One ego cut (admit “I don’t know”).
10/ 📆 Track it for 52 weeks. No drama.

If you’re comfortable, you’re de-training.

I wrote the full story here:
The Unfair Advantage That Never Retires

Read it on BRIDGE: https://lnkd.in/gwax-Asg

Where are you still willing to be bad at — on purpose?

📩 Want help building your 52-week plan? Talk to me.
📬 Subscribe to BRIDGE: https://lnkd.in/gCdavukQ

♻️ If you want to help create great leaders — repost this and help others.
➕ Follow Adi Agrawal | Bridge the Gap

When two execs disagree, you can be the answer.

And later, you may become the blame.

Don’t “manage the ambiguity.”
Force the decision back to where it belongs.

Here’s what I coach leaders to do when
two executive leaders want different outcomes:

One wants speed.
One wants control.
One wants growth.
One wants cost.

They’ll send you off with:
“Use your judgment.”

That’s not empowerment.
That’s a risk transfer.

Run this in 15 minutes:

1/ Write the choice in one line
“We will do A, not B, for the next 30 days.”

2/ Write the tradeoff in one line
“A gives us X, but we accept Y.”

3/ Write the cost of delay in one line
“If we don’t decide by Friday, we lose Z.”

Put both leaders in the same thread
Same note. Same words. No side meetings.
Ask one question
“Which tradeoff are you choosing?”

Then send the recap the same day.

This is people-first leadership.

Because if you don’t force the call upward, your team pays:
conflicting priorities, weekend work, and whiplash.

Clarity is a leadership act.


📬 Subscribe https://lnkd.in/gpFa7-gW
♻️ Repost to help leaders stuck in exec crossfire
➕ Follow Adi Agrawal | Bridge the Gap

Promotions aren’t a reward.

They are a risk transfer.

Your boss is taking some of your risk
and carrying it upward.

That’s why “I delivered a lot”
often isn’t enough.

Delivery is backward-looking.

Promotions are forward-looking.

They’re about one thing. 

Can we trust your calls
when the next quarter gets messy?

⸻

Most strong operators get stuck
because their work is visible
but their judgment is not.

Leaders above you don’t see:

What you…

• stopped early
• refused to promise
• simplified
• escalated before it spread
protected (customers, team, quality)

So when they’re asked,
“Why should we promote them?”
they can’t answer.

They believe you’re good.

They can’t prove you’re a good bet.

⸻

Make your judgment easy to see.

Not with a story.

With a simple “Calls + Proof” list:

The call you made
What you gave up
Risks you reduced
What changed after

No adjectives.
No “strategic.”
No “aligned.”
Just facts.

Examples:
•	We moved the date 2 weeks. Defects dropped. Customer stayed.
•	We cut scope. Shipped the core. Renewed on time.
•	We said no to a custom request. Support load stayed flat.
•	We escalated a dependency early. Avoided a miss.
•	We stopped a meeting. Reclaimed 6 hours/week. Output increased.

⸻

This is the shift:

Stop presenting yourself
as someone who “works hard.”

Present yourself
as someone who makes good calls
and protects outcomes.

Because that’s what leaders promote.

Not effort.

Judgment with outcomes. 

⸻

If you were being promoted tomorrow,
what are the 5 calls you’d want on your list?

📩 Want help turning your last 60 days into a promotion-grade “Calls + Proof” page? Talk to me.
📬 Subscribe to BRIDGE: https://lnkd.in/gCdavukQ

♻️ If you are a high performer, repost this. Help others.
➕ Follow Adi Agrawal | Bridge the Gap

A job isn’t a title.

It’s your days — day after day.

Most career regret comes from one mistake:

We choose the idea of the work.
Not the life the work creates.

On BRIDGE this week, I share three stories.
Different people. Different decisions. Same lesson:

Learn the day-to-day first.

Because the work you choose has to be work you can do —
and still be yourself — every day.

Before you accept any role that feels “great”:

1/ Talk to 3 people doing the job right now
Break down a normal week, start to finish

2/ Ask what the job is really made of
What takes the most hours
What drains the most energy
What you get blamed for when things break
Why good people burn out

3/ Ask blunt questions
Would you take this job again?
What surprised you after you started?
What did you wish you’d known?

Get real answers.
Then decide with your eyes open.

Read the three stories on BRIDGE:
https://lnkd.in/gCdavukQ

📩 Want help pressure-testing a role before you say yes? Talk to me.
📬 Subscribe to BRIDGE: https://lnkd.in/gCdavukQ
♻️ If you are a high performer, repost this. Help others.
➕ Follow Adi Agrawal | Bridge the Gap

AI assistants were the warm-up.

2026 is about agents.

Not tools that draft.
Systems that take actions inside workflows.

Most enterprises won’t “flip a switch.”
They’ll do the disciplined path:

sandbox → limited pilot → guarded rollout
then more teams, more systems, more edge cases.

And the real risk will show up.

Not on day 1.

In week 8 or 10, when someone says:
“Let it do this one action.
We’ll keep the rest manual.”

Then another team asks.
Then another exception gets approved.

And soon the agent can touch:
refunds, pricing, customer records, access.

Each action looks small.
But the blast radius is huge.

And when something goes wrong,
it won’t look dramatic.

It’ll look like:
a thousand tiny wrong actions done fast
in the quiet parts of the business
before anyone notices.

Governance for agents isn’t
principles and statements.

It’s operational control.

What CEOs need to have in place before scale:

1/ Action boundaries
What it can do. What it can’t.

2/ Approval gates
Which actions require a human “yes.”

3/ Access + limits
Least permission. Tight scopes. Rate limits.

4/ Replayable trail 🔁
Input → instruction → action → result
with time + version history.

5/ Same-day stop 🧯
Clear triggers, escalation, kill switch.

What getting blindsided looks like:

• Access creep through “exceptions”
• Manipulated inputs (tickets, email)
• Behavior shifts after tuning/updates
• Quiet customer harm at scale
• Human harm: pressure, blame

Govern agents even more carefully than payments.

Because soon, they’ll touch money, trust,
and people – whether you meant to or not.

📩 CEOs, Board Members: Want my help with AI Risk? DM me
📬 Subscribe: bridge.adiagrawal.com

♻️ Repost to your network managing AI and tech risk
➕ Follow Adi Agrawal | Bridge the Gap

Boards are getting blindsided by AI.
Not because they missed the tech.

Because they are still not governing it 
as a decision system.

Good board-level AI governance is this:
You don’t “approve models.”
You govern where AI is allowed to shape reality.

What you should demand:

1/ Decision map
Which business decisions are AI-influenced today,
which ones next quarter,
and which ones are off-limits.

If you can’t name the decisions,
you can’t govern the risk.

2/ Evidence trail
Not assurances. Evidence:
inputs → instructions → outputs
model/version + timestamp
what changed since last quarter

If you can’t replay it,
you can’t defend it.

3/ Change control
Model updates are releases, not tweaks.
Show the change log,
test evidence,
and a rollback plan.

No rollback = no governance.

4/ Stop controls
Pre-set circuit breakers:
drift, anomalies, fraud signals, data breaks.
Same-day stop.
Clear escalation.

AI failure rarely manifests at once.
It spreads quietly.

What boards should not be blindsided by in 2026:

• Shadow AI inside teams and tools
• “Automation risk” (bad actions at scale)
• Data contamination and weak lineage
• Agentic workflows that take actions, not advice
• Deepfake and impersonation fraud
• Human impact: trust, fairness, job pressure

If your oversight is a quarterly update
and a vendor assurance,
you’re not governing AI.

You’re blindly approving exposure.

📩 Executive Leaders; Board members: want a Board AI Oversight Pack? DM me

📬 Subscribe to BRIDGE: https://lnkd.in/gCdavukQ

♻️ Repost to your network of high performance seeking leaders
➕ Follow Adi Agrawal | Bridge the Gap

If your boss stopped backing you, you’ll notice it
before anyone says it.

Leaders I’ve led and coached (100s)
describe the same few signs:

• Your name stops getting mentioned.
• Your decisions get “checked” again.
• You hear about things late.
• You get pulled into cleanup work.
• You’re asked to “align” more than you’re asked to lead.

Nothing is said.
But the rules change.

Use this reset plan I coach leaders to run
immediately:

1/ Capture the pattern (not the emotion)
Write 5 examples. Date. Meeting. People.
This is your evidence, not your story.

2/ Force a 30-day expectation in writing
In your next 1:1 ask:
“What are the 3 outcomes you need from me in 30 days?”
“What would make you lose confidence in me?”
Send a recap email the same day.

3/ Build weekly proof
Pick 3 measures that match the outcomes.
Share progress every Friday.
Short. Factual. No spin.

4/ Close one gap with a key peer
Ask: “What’s one thing you need from me this month?”
Deliver it once, cleanly, and on time.
Let your boss hear it from the business.

5/ Stop taking on work that sideline you
Say yes to work that moves outcomes.
Say no to work that makes you the safety net.

Support doesn’t return because you work harder.
It returns when your boss can point to proof
and stop worrying about surprises.


📩 If you’re a leader in need of a strategy: DM me.
📬 Subscribe: https://lnkd.in/gpFa7-gW
♻️ Repost to inspire your network of high performance leaders
➕ Follow Adi Agrawal | Bridge the Gap

If “customer centricity” is real,
it shows up in what your customer experiences.

Not in what you say.


Your customer doesn’t feel your strategy.
They feel your friction.

They feel it when they:

Hit a policy wall
Get bounced between teams
Have to repeat the story
Wait with no owner
Get “we’ll look into it” instead of an answer

That moment is your real brand.

⸻

Most companies treat customer centricity like a belief or a slogan. 

Customers experience it like a cost.

Time.
Effort.
Uncertainty.

So the real question isn’t:

“Did we listen?”

It is:

“Where did we make the customer do “our” work?”

Because every time you push work onto the customer,
you burn trust.

⸻

Run this test.

Pick one simple journey:

Cancel
Refund
Renew
Fix a billing error
Get help during an outage

Now ask:

“How many steps did we make the customer take
that we could have taken for them?”

That number is your customer centricity score.

Lower is better.

⸻

Fix it with one visible habit.

Every week, ship one friction removal.

Write it in customer language:

What they hit
What we changed
When it’s live

Example:

“Customers had to call to cancel.
Cancel is now self-serve.
Live Friday.”

No deck.
No committee.
Just fewer steps for the customer.

⸻

Where are customers doing work
your company should be doing?


📩 Want help finding and removing the highest-cost customer friction? Talk to me.
📬 Subscribe to BRIDGE: https://lnkd.in/gCdavukQ

♻️ If you are a high performer, repost this. Help others.
➕ Follow Adi Agrawal | Bridge the Gap

You walk into a review.
They ask what you delivered.
Your mind goes blank.

Not because you did nothing.
Because you didn’t write it down.

Mid-career and senior work doesn’t show up
as neat deliverables.

It shows up as:
• hard decisions made early
• risk removed before it spreads
• teams unblocked
• customers kept
• problems that never became a fire

Then the “tell me your impact” moment arrives:
- Review
- Promotion conversation
- Board update
- Interview

And your brain does what brains do:
it remembers the last crisis,
not your real body of work.

I’ve worked with 100s of leaders.
The best ones don’t rely on recall.

They keep evidence.

Ten minutes a week.
Same day every week.

Personal Scoreboard

1/ Decisions I made
3 bullets

2/ Risks I reduced
what didn’t happen because I acted

3/ Outcomes
time, quality, cost, revenue
any real signal

4/ People impact
who grew, what got easier

5/ Lesson
what I’d repeat, what I’d change

This becomes your raw material for:
reviews
promotions
exec updates
interviews

Because it’s real.

What’s one decision you made this week
that you’ll forget next month
if you don’t capture it?

📩 Want help setting up scoreboards? Talk to me. 
📬 Subscribe to BRIDGE: https://lnkd.in/gCdavukQ

♻️ If you are a high performer, repost this. Help others.  
➕ Follow Adi Agrawal | Bridge the Gap

Platforms don’t stall from competition.
They stall from broken loops.

If you live in the real world,
These Four Horsemen show up again and again.

1/ The Feature Farmer
More shipped. Less stick.
Activations bump up. Retention stays flat.

2/ The Silo Builder
Teams optimize parts, not the loop.
Handoffs grow. Cycle time explodes.

3/ The One-Sided Deal
They subsidize one side
and quietly punish the other.
Growth looks good. Margins don’t.

4/ The Migration Mirage
Grand “announce a sunset”
without an off-ramp people will take.
So legacy never dies.
You just end up running two worlds forever.

Antidote (3 moves):

1. Map one loop: acquire → activate → retain
2. Price both sides (with a reason)
3. Migrate in stages: new rails → incentives → cutover

Board/CEO test (60 seconds):

• What is the one loop we’re funding?
• Which step is the bottleneck today?
• What is the hard date we stop dual-run?

📩 If you’re a CEO/Board member funding “platform,”
DM me HORSEMEN and I’ll send my 5-question
Platform Loop Test we use in governance reviews.

📬 Subscribe to BRIDGE: https://lnkd.in/gCdavukQ

♻️ If your team owns a platform roadmap,
save this and share it before the next QBR.

➕ Follow Adi Agrawal | Bridge the Gap

I’ve watched companies cut roles
and then spend a quarter
trying to rebuild what they cut.

They don’t cut “a person.”
They cut a capability.

That’s what Casey was.

Quiet. Reliable.
The seam between teams.
The person who stopped small fires
before they became incident calls
and customer churn.

Then he got the invite:

“Quick Sync – 5 minutes.”
No agenda. No context.

Script. Severance.
Access ends immediately.

And inside the company?

Nothing “collapsed.”
It frayed.

Escalations got loud.
Decisions turned into rework.
Teams built overlapping fixes.

The model didn’t see any of that.

Because models don’t measure:
prevented failures
execution glue
human judgment
trust.

If you sit on a Board
or own a P&L, save this.

Before you cut a role, ask:

• What do they prevent from happening?
• Where do they reduce customer pain?
• Which handoffs do they “unstick”?
• What breaks in 30 days without them?
• Who will do this work on Tuesday?

If you can’t answer in plain words,
You’re guessing.

I’m publishing Casey’s Story.
If you’ve ever approved cuts
from a calm room and a clean deck,
read it.

Who’s the “Casey” in your org
that your spreadsheet can’t see?

📩 Want the pre-cut execution audit I use to spot roles that prevent incidents, churn, and rework?
DM SEAMS and I’ll send the one-pager.

If this made you think of one decision
you wish you could redo:
♻️ Repost to your network of high performance seeking leaders

➕ Follow Adi Agrawal | Bridge the Gap

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