Fintech Sales Strategist & Leader → I merge 25 years of Fintech sales + banking to guide founders from chaos to closed revenue | Advice for selling to financial institutions

If you’re building a great product but struggling to get traction with banks, I help you fix that.

From first intro to final contract, I walk alongside founders to shorten sales cycles, navigate complex buying committees, and build deals that don’t rely on deep discounts.

This isn’t just something I coach on.  It’s something I’ve lived for the past 28 years from a career that spans both worlds:

→  Started as a teller at 19 in a town of 7,500 → earned my way into community banking
→  Spent 23 years at a big-three core, mastering complex sales and buyer journeys
→  Fell in love with sales demos, boardrooms, and turning "nos" into long-term "yeses"
→  Grew into quota-carrying sales leadership, built channels, launched fintech verticals
→  Went deep into BaaS and embedded banking → and learned the value of these partnerships

That journey shaped what I now call the Bank-FinTech Partnership Methodology - a practical, hard-won approach I’ve used (and refined) alongside founders to navigate real-life banking sales cycles, complex buying committees, and long timelines.  It’s not theory.  It’s what actually works when you're in the weeds trying to turn conversations into contracts.

Here’s how we build those bridges together:

↳ Diagnose why your fintech isn’t gaining traction with FIs
↳ Develop a GTM strategy tailored to financial institutions
↳ Translate your innovation into boardroom-ready language
↳ Create a sales process that doesn’t rely on deep discounts
↳ Build trust that converts complex conversations into signed partnerships

👩‍👧‍👦 At home, I’m raising three future fintech execs with my husband - a community bank exec and BaaS strategist. Dinner conversations at our house sound like fintech-banking peace negotiations.

🛠️ At work, I serve as a fractional sales strategist, speaker, and ecosystem builder, helping teams go from chaos to closed without burning bridges in the process.

Ready to stop guessing and start growing?

📅 Book a Free 30-Minute Strategy Call (you’ll walk away with one actionable takeaway):
https://calendly.com/stacybishop20/20_intro

 Not quite ready?  

🗞️ Subscribe to Selling Fintech:  https://sellingfintech.kit.com/e1ec3c973c
➕ Follow me here for real stories, frameworks, and founder-first sales advice.

Stacy Bishop

I have closed $100M+ in contracts with banks and credit unions.
I have built sales teams, banking verticals, and strategic partnerships from scratch.
Here are my 5 Core Principles for closing bank deals: 

1. I get to know who I’m selling to as a person: 
Before I talk about product, I learn who they are, their role, pressures, goals, and how they actually work day-to-day. People buy from people they trust, not from feature lists.

2. I make sure I understand their problem:
Real selling starts with listening. I dig into where the pain lives, how it shows up in their workflow, and what it costs them in time, money, and stress. 

3. I don’t overcomplicate communication:
Once I understand their pain, I connect the dots in simple, clear language. No jargon. No buzzwords. I show how my solution fixes the problem, saves time, or reduces friction. If they can’t repeat the value back to me, I haven’t explained it well enough.

4. I sell to the group not the champion:
Big deals never come down to one person. IT, compliance, risk, operations, and leadership all have a vote. So I build trust with the entire committee and speak to what each person cares about.

5. I put risk reduction at the center
Banks don’t buy features. They buy safety, clarity, and control. Always show how the solution lowers risk — operational, compliance, and reputational.

You don’t win enterprise deals with buzzwords and hype.
You win them by knowing the people, naming the problem, and removing every point of hesitation.

#Fintech BaaS #Banking

JSESSIONID

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Talks about #hr, #banking, #payroll, #partnerships, and #earnedwageaccess

Bank <> FinTech Partnership Broker || Former Revenue Leader at Jack Henry || 🎤Keynote Speaker

I have closed $100M+ in contracts with banks and credit unions because of one thing…  
And it has nothing to do with AI or product. 
I build a relationship with the human first. 

Senior executives in banking don’t make enterprise deal decisions because of feature lists. They make decisions based on trust, clarity, and confidence in the person and team they’re going to partner with.

The holiday season is one of the most effective windows of the year to strengthen that trust if you approach it correctly. 

Here are three ways to do that: 

1. Send a year-end acknowledgment with zero agenda.
Not a pitch. Not a CTA. A simple, intentional note recognizing something meaningful in their year; a leadership move, a strategic shift, an initiative you know took serious effort. Executives remember who pays attention.

2. Ask one strategic question about their upcoming year.
This time of year, leaders are thinking in terms of Q1 priorities and resource allocation. A single question can open a real conversation: “What outcome is non-negotiable for your team in Q1?” It signals that you’re thinking about their world, not your quota.

3. Offer a short, informal year-end industry debrief. 
Not a sales meeting, a conversation between operators. Fifteen minutes to compare observations on risk, regulation, technology shifts, or operational pressure points as they look ahead to 2026. Executives value peers who think at their level.

This is how major B2B deals begin.
Stop leading with product.
Start leading with human connection.

#Fintech #BaaS #Banking

Last week, our kids came home wearing these to celebrate the 67th day of school. If you have young elementary-age kids, or have spent more than five minutes around them, you already know why that number matters. Somewhere along the way, “six, seven” turned into a full-blown phenomenon. And they don’t just say it. There’s flair. There’s tone. There are hand motions. Six. Seven.
It spread through our house earlier this year like wildfire. 
Which led me to a question I can’t get out of my head.
Has anyone successfully worked “six seven” into a business conversation?
I’m talking banker-to-customer. 
Vendor negotiations.
Fintech-to-bank. 

For example:
• “We can offer you 4.67%.”
• “What if we structure this as a six- to seven-year term?”
Ridiculous? Absolutely.
But also… kind of funny.

If you’ve found a way to sneak “six seven” into a serious business discussion, I need to hear about it.

Someone reached out and asked me, “Can you build rapport remotely?”
He’s a founder that doesn’t have the time to go chase every deal in person.
My answer is a resounding ABSOLUTELY and here’s why… 
(listen to the video to hear what I have to say)

Stop discounting your Fintech.

If you're constantly slashing prices, it's a symptom, not a tech problem.

It means you haven't proven your value.

Here's how to differentiate your Fintech product effectively:

𝗡𝗮𝗶𝗹 𝗬𝗼𝘂𝗿 𝗢𝗳𝗳𝗲𝗿: 
→ Understand how your product is truly different.
→ What unique problems do you solve?
→ How do you package it to make it a 'low lift' for the bank?

𝗖𝗿𝗲𝗮𝘁𝗲 𝗜𝗺𝗽𝗮𝗰𝘁𝗳𝘂𝗹 𝗣𝗿𝗲𝘀𝗲𝗻𝘁𝗮𝘁𝗶𝗼𝗻𝘀: 
→ Start with the banker's challenge.
→ Avoid feature-dumping.
→ Use a challenger sales methodology to point them uniquely towards your solution.

𝗚𝘂𝗶𝗱𝗲 𝘁𝗵𝗲 𝗖𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻: 
→ Don't ask, '𝘞𝘰𝘶𝘭𝘥 𝘺𝘰𝘶 𝘭𝘪𝘬𝘦 𝘵𝘰 𝘵𝘩𝘪𝘯𝘬 𝘢𝘣𝘰𝘶𝘵 𝘵𝘩𝘪𝘴?'
That's not a next step. It's an invitation to pause.

→ Instead, proactively book the next meeting.
'𝘖𝘶𝘳 𝘯𝘦𝘹𝘵 𝘴𝘵𝘦𝘱 𝘪𝘴 𝘟, 𝘪𝘧 𝘵𝘩𝘦𝘳𝘦'𝘴 𝘷𝘢𝘭𝘶𝘦, 𝘭𝘦𝘵'𝘴 𝘧𝘪𝘯𝘥 𝘢 𝘵𝘪𝘮𝘦 𝘪𝘯 𝘵𝘩𝘦 𝘯𝘦𝘹𝘵 𝘸𝘦𝘦𝘬 𝘰𝘳 𝘵𝘸𝘰.'

𝗣𝗿𝗼𝘃𝗲 𝗩𝗮𝗹𝘂𝗲 𝗘𝗮𝗰𝗵 𝗦𝘁𝗲𝗽: 
→ Provide something impactful at each step to help with the evaluation.
→ Build micro-agreements throughout the process.
→ Showcase your professionalism and authority.

When you get to negotiation, the value should already be undeniable.

Bankers have endless tasks in front of them.

Give them compelling reasons to say YES, not just reasons to discount you (𝘢𝘯𝘥 𝘺𝘰𝘶𝘳 𝘱𝘳𝘰𝘥𝘶𝘤𝘵).

Banks exploring embedded finance often reach the same point. 

At some stage, there's a need to understand how to monitor partner activity in a way that supports growth and satisfies exam requirements.

This session takes a practical look at transaction monitoring inside a BaaS environment and the changes that occur when fintech partners and their end-users begin moving money through your charter.  

You will learn how sponsor banks build visibility, stay ahead of suspicious activity, and manage alerts without slowing down innovation.

If you are evaluating BaaS or already onboarding partners, this conversation will help you understand the expectations and the tools that make it manageable.

Katelyn O'Brian, CBAP, Hanna Kness and 322 other attendees

BaaS Layers & Players:  Transaction Monitoring

Wishing great success to each of you as you chase December closings!

For those of you already looking ahead to 2026, here's your guide to selling your Fintech solution to bankers in a new year and ever-changing landscape.

By Stacy Bishop Selling technology to financial institutions is a different kind of sales motion. Over the past 25 years in banking, fintech, and fina

Open article: How to Sell to Banks as a Fintech in 2026: Lessons From $100M+ in Closed Bank Deals by Stacy Bishop • 6 min read

How to Sell to Banks as a Fintech in 2026: Lessons From $100M+ in Closed Bank Deals

Selling to banks and credit unions isn’t about a great product. It’s about proving you can operate in one of the most heavily regulated environments in the world. 
And yet…

I still see founders take a cavalier approach:“We’ll figure it out later.”
“We’ll fix compliance once it becomes a problem.”

That mindset will cost you partnerships and slow down your ability to scale. If you’re a fintech founder trying to scale beyond your first few banking partners, here’s one great piece of advice: 
Let banks do what they do best in a partnership. 
Know what you know and know what you don’t know.

Over the past two years, especially with embedded finance, we’ve watched the same mistakes repeat:
• Fintechs stepping into the bank’s lane
• Banks stepping into the fintech’s lane
• Both sides losing clarity on who owns compliance obligations

The result?
Confusion, risk exposure, delays and in some cases, regulatory scrutiny.

The founders who win share one trait: They stay laser-focused on their core competency and bring in real compliance expertise early. Because in this industry, not taking compliance seriously could very easily cost you everything. 

#Fintech #BaaS #Banking

This time of year is often confused for the "let's wait until January to reach out" season.

Avoid that knee-jerk reaction and begin to form a relationship today with bankers you hope to partner with next year.  

But not with a cold outreach message you are sending to every other banker.  Be smart and strategic.

I get into this further in this week's newsletter.   👇

From Someone Who Has Closed $100M+ With Banks After 28 years working across community banks, a big-three core, and fintech sales leadership, I can tel

5 Ways FinTech Founders Can Build Relationships With Banking Executives During the Holidays

It’s not the banker’s job to tell you their process.
It’s not the banker’s job to follow up.
And it’s definitely not their job to guide your next steps.

That’s on you as a Fintech founder selling to banks.

If you want to win in this market, show up with a plan that proves you’ve done this before, many times.

Lay out the happy path:
👉 Here’s Step 1.
👉 Here’s exactly where we are today.
👉 Here’s what happens next.
👉 And here’s who needs to be in the room — CFO, CRO, and anyone who shapes the decision.

You’re not asking them to figure it out.
You’re leading them through a proven buying journey.

When you set the North Star and drive the process with clarity, nobody wonders what happens next, they follow your lead. 

This is how you shorten cycles, earn respect, and close deals with banks in 2026.

#BaaS #Fintech #Banking #Leadership

When Synapse collapsed, regulators didn’t call the middleware providers.
They didn’t call the fintechs.
They called Evolv, because the bank sponsor is accountable for oversight.

And that’s why your Third-Party Risk Management can’t be “good enough.”
It needs to be airtight.

Because in embedded finance:
• Every partner’s controls are your controls.
• Every oversight gap becomes your exposure.
• Every compliance weakness becomes a future supervisory event.
• Every program requires continuous — not quarterly — monitoring.

TPRM has officially graduated from a “compliance box-checking exercise” to a strategic risk discipline that defines which banks win in the next era of embedded finance.

If you want to understand what airtight TPRM actually looks like, click here to watch the replay from a recent session I hosted with several experts and community banking executives who are building high-performing, high-compliance programs in real time: 

https://lnkd.in/gsy7WBa5

Interested in how my middle school dating life relates to selling your Fintech solution to bankers?  

Including some of the "secrets" inside.  👇

In middle school I “dated” in the most PG-sense of the word. I might sit with someone at lunch, pass a folded note in class, or hold hands on the walk

7 reasons banks don’t “date” fintechs

Do you get a banker on the phone and begin showing your solution shortly after learning their name?

I beg of you... STOP.  

Instead, use the first meeting strategically.  Here's how... 👇

Hi! I’m Stacy. I still remember the first time I landed a meeting with a bank after weeks of chasing. The COO said, “We’d love to see how it works.” M

Don't demo during discovery (unless you want to be ghosted by bankers)

I have closed more than $100 million in contracts with banks and credit unions. 
Here are 5 core principles for closing bank deals: 

1. I get to know who I’m selling to as a person. 
2. I make sure I understand their problem. 
3. I don’t overcomplicate communication. 
4. I sell to the group not the champion
5. I put risk reduction at the center

REMEMBER: Banks buy safety, clarity, and control. 

#Fintech #BaaS #banking

No alternative text description for this image

Fintech Founders:
AI is not your differentiator.
Stop leading with it.

Every banker you’re selling to already assumes your product uses AI. 
It’s the baseline now → and will be even more so in 2026.
It’s not the value prop.

If you want to stand out and close deals with banks:
→ Start with the bank’s real problems.
→ Speak to the pain in their current state.
→ Show the exact outcome your solution unlocks.
→ Then, only then, use AI as the supporting mechanism of your solution, not the headline.

Banks don’t buy “AI.”
They buy reduced risk, speed, compliance, and confidence.
Lead with what matters to them.

It's fun to win.

Showcasing compliance maturity in bank sales may not be your idea of fun.

But it certainly helps you win.

So maybe, just maybe... compliance can be fun after all.

It's normal for Fintech founders to assume that winning a bank partnership is about presenting a superior product, demonstrating their gorgeous UX, or

The Psychology of Selling to Banks: The One Factor That Will Increase Your Odds as a Fintech

There are people, and there are companies that the industry needs to know about.

Sometimes these companies get lumped into categories alongside others, where you have to squint to see the similarities.

Or the people have backgrounds so strong and storied that you marvel at how lucky you are to be on a Google Meet with them.  

These are the companies that I cheer for, and the people I want to work with.  

I can say with absolute certainty that ZorroFi and Sandra Wasicek-Woegenstein | Armin Wasicek, check all of these boxes for me.  

Plus they are genuine and kind people... just trying to make the front-end messy side of lending better.

I'm thrilled to advise the ZorroFi team, and invite you to check them out.  You won't be disappointed.

Founder & CEO, ZorroFi | Turning Risk Management Into Growth Infrastructure for Community Banks, Credit Unions & CDFIs | Berkeley SkyDeck Pad-13

View Sandra Wasicek-Woegenstein’s profile

Gratitude highlight today: Stacy Bishop. 🍁💛

Stacy recently joined us as an advisor to ZorroFi, and we are truly grateful for her support.

She’s one of those rare people who brings clarity, warmth, and decades of real industry experience into every conversation. Stacy has helped me stay focused, grounded, and aligned with what matters most when building for community financial institutions.

I’m thankful for her guidance - and even more thankful for her heart.

Thank you, Stacy. 🙏

As a fintech founder selling to banks, go slow before you go fast.
Here’s what I mean:

Master the fundamentals.
1. The offer: If your offer isn’t precise, bank-ready, and differentiated, you’re already losing. Banks don’t buy vague promises. They buy risk reduction, revenue expansion, or cost efficiency—spelled out in plain language.

2. The ICP: Most founders aim at the CEO. Wrong target. The CEO is influence, not ownership. The real decision-makers live in the buying committee: heads of product, compliance, risk, operations, and sometimes IT. If you can’t name the exact persona who feels the pain you solve, you can’t sell to a bank.

3. The sales cycle: Bank deals don’t “close when they’re impressed.” They close when you understand how the bank actually buys. Map the journey. Know who signs, who blocks, who delays, and who champions. Your messaging must reflect the steps, the risks, and the internal politics of the institution.

When you master the fundamentals, sales accelerate. 

#BaaS #Fintech #Banking

"Fit" may be an "F" word, but one that I highly encourage you to use all the time in your bank.

Welcome to BaaS for Bank Leaders, your weekly guide to making sense of Banking as a Service (BaaS). Here you will get practical insights into the real

BaaS Launchpad Step 5:  The secret to selecting the right fintech partners

It's never too late in the year to kick off your next sales cycle → or as I like to phrase it, "Buying Journey" with bankers.

I've included tips in this week's newsletter, along with a checklist to ensure your time with bank and credit union prospects is never wasted. 👇

Early in my career at Jack Henry, I made a mistake that most green fintech salespeople make. I walked into a meeting with a bank executive armed with 

Fintech Sales Strategy to Win Partnerships with Banks: What I Have Learned from 23+ Years in B2B Sales

SaaS Sales Leader | Writer | Keynote Speaker

Elite Performance with Humanity

Most leaders and teams don’t struggle with talent.

They struggle with execution, especially when pressure, complexity, and hidden struggles get in the way.

I’ve been there.

For 25 years in corporate sales and leadership, I watched high performers hit their numbers while quietly burning out. 

I lived that story myself, winning on the outside while battling panic attacks behind the scenes.

What I learned is this:

The difference between good and elite isn’t more hustle. 

It’s the mental frameworks, habits, and systems that make success sustainable, without sacrificing your humanity.

That’s the work I do now.

I help leaders, executives, and sales teams:

- Build the mental models that drive consistent execution

- Install elite habits that separate top performers from the rest

- Remove the interference that keeps people from their best work

Ways We Can Work Together

- Consulting & Advising – Partnering with leadership teams to drive growth, performance, and culture change

- Speaking & Workshops – Keynotes and interactive sessions that create lasting behavior change

- Coaching – One-on-one work with high performers to unlock their next level with intention

If you want a culture where execution, focus, and humanity work together, and where people can win without losing themselves, let’s connect.

📩 DM me or email jon@jongiganti.com


Jon Giganti

My son, Gabe, turns 18 today.

He made me a dad. It feels like yesterday when he showed up in this world.

Time…slow down!! 🙏🏼 

But that’s life. The days are long and the years are short.

I’m so inspired by Gabe.

He’s been battling since day one. His umbilical cord was wrapped around his neck at birth for a couple minutes. We had some scary moments early, but he fought and he survived. 

That’s who he is. 

He’s taught me more about resilience than any book or coach ever could.

In 7th grade, his basketball coach called me during tryouts and told me Gabe should probably just focus on soccer. But he loved basketball. And I knew—deep down—that he had something. He was undersized and in his head a lot. It just felt way too early to write the sport off.

So we pulled him out and let him play rec ball. He kept working. He kept growing. And he didn’t quit.

Fast forward to today: he’s a starting guard on the #2-ranked team in Ohio (D7). His senior year. A testament to the unseen hours. The early-morning sprints. The gym sessions we rent out where I get to rebound for him. (I’m a former soccer/wrestling guy… basketball is definitely not in my blood!). Rebounding suits me just fine! 

But here’s what I love most:

He’s a great kid. He looks people in the eye when he meets them. Gives a firm handshake. Means it when he says “nice to meet you.”

He’s funny, but not overly extroverted. He likes his downtime. He taught himself guitar and piano…thank you, YouTube.

When he was working on his college essay, I asked him why he’s such a pass-first guard. His answer hit me good…he loves helping others succeed. He wants to be the guy who sets people up.

I didn’t show it, but that one got me emotional. Because, that’s the whole game. When you realize life isn’t about you—it’s about serving others—that’s when doors start opening.

I don’t know exactly what’s next for him. College… maybe. Military… maybe. Starting a business… maybe. Who knows.

But I do know this…his grit, humility, and heart for others will carry him wherever he goes.

There have been hard moments. School hasn’t come easy. Sports haven’t always come easy. 

He can be his own worst enemy (wonder where he gets that from…). 😊

But for any parent who’s watched their kid struggle…there’s hope. 

Keep pouring into them. Keep encouraging them. Keep loving them fiercely.

The days fly by, but the seeds you plant will grow.

Being a dad has been the greatest honor of my life. And I can’t wait to watch Gabe’s impact unfold.

Happy 18th, buddy.

Here's the irony that hit me recently.

My last name is Giganti. It literally means "big" in Italian. And I've spent most of my career playing small.

Sitting in meetings at my old software company, deferring to everyone. 

Looking at someone's title or education and thinking I didn't belong. Holding back my ideas because maybe someone smarter should speak first.

Sound familiar?

Here's what I've realized after 11 months of building my own thing: We ALL do this. Every single one of us has moments where we play smaller than we should. And it's costing us everything.

Not just the deal we didn't close or the opportunity we didn't take. 

It's the impact we're NOT having. The people we're NOT serving. The brilliance we're keeping to ourselves.

We tell ourselves we're being humble. But really? We're just afraid of what people might think.

Afraid we'll look arrogant. Afraid we'll fail. Afraid we don't actually belong in the room.

So, we play small. 

We defer. We wait for permission. We let our fear decide our ceiling.

I saw this shift at a conference recently. 

First time going as my own company. And something changed in how I showed up. I wasn't trying to impress anyone. 

I was just showing up as someone who belongs. 

Asking questions. Being curious. Treating every conversation like "are we a match?" instead of "please validate me."

That's the shift. 

From playing small to playing big. And before you think this is about ego or cockiness, let me be clear: It's not.

Playing big isn't about being the loudest person in the room. 

It's about believing you have value to offer and actually offering it.
It's about realizing that when you play small, you're not just hurting yourself. You're hurting everyone who could benefit from what you bring.

So, here's my question: Where are you playing small right now? And what's it costing you?

Flying to DC today to lead a workshop with Copart’s sales team on Wednesday.

Here’s what I know after years of doing this work: The real transformation doesn’t happen during my session. 

It happens in the unseen hours. 

The conversations before I ever step on stage. The trust built through genuine presence, not performance.
So I’m showing up today. 

Sitting in their team sessions. 

Listening. Learning their challenges. Building authentic relationships before I share a single framework.

When their team said “better habits” was their #1 need, that wasn’t just data. 

It was an invitation to show up with intention. To be helpful first, good second.

Then my flight got canceled this morning. 

Just boarded six hours after I was supposed to. I could let that derail me. Or I could remember what I teach: setbacks are just data. 

How we respond is where the meaning lives.

This is the difference between reactive leadership and intentional leadership. One lets circumstances control the narrative. The other uses every moment, even the frustrating ones, as an opportunity to live the message.

The irony isn’t lost on me. 

I’m about to teach about systematic approaches to sustainable excellence, and I’m getting a real-time reminder that vulnerability isn’t weakness. It’s the foundation for authentic authority.

Copart , I’m ready and so excited to see you all. 

Not because everything went according to plan, but because the work of transformation never does. 

That’s where the real growth begins.

I need to be honest with you about something.

This playing bigger thing? It's a daily battle for me too.

Every single day, I wake up and have to make the choice. 

Play big or play small. Show up or hide. Offer my brilliance or keep it safe.

There's a Bible verse that's been hitting me lately. John 10:10. It says the enemy comes to steal, kill and destroy, but Jesus came to give us life to the fullest.

And regardless of your faith, here's what's true: We're under attack. 

From our own doubts. Our own fears. Our own insecurities.

We're our own worst enemy way too often.

I'm standing shoulder to shoulder with you on this. It's not like I figured this out and now I'm good. It's a daily choice. A battle.

Some days I win. Some days I don't.

But here's what I've learned: Playing bigger isn't a feeling. It's a choice.

You don't wait to feel confident. You choose to act confident and the feeling follows.

You don't wait to feel like you belong. You choose to show up like you belong and eventually you believe it.

That's why I named my company Giganti Group. It's aspirational. Even for me.

Every day I see that name and I have to ask myself: Am I living into it? Am I playing as big as my name suggests? Or am I playing small again?

Most days, honestly, I'm somewhere in the middle. Working on it. Tracking it. Getting better.

That 5 to 8.5 shift I mentioned? That's real progress. But it's not done. I'm not at a 10. 

Maybe I never will be.

But I'm choosing to move forward. Daily.

Here's what I want you to know:
You're not alone in this fight. We're all battling the same doubts. The same fears. The same voice that says "who do you think you are?"

But we get to choose. 

We get to play big. We get to live into our brilliance.
Not because we feel like it. But because we choose it.

How do you win today? How do you play bigger today?

Remember, it's not about cockiness. It's not about ego. It's about belief.

Belief that you have something valuable to offer. 
Belief that when you play small, people miss out on what you bring. 
Belief that you were made for more than hiding.

I love Todd Herman's work on alter-ego. We all need it. We all need that version of ourselves who plays bigger. 

Who shows up. 
Who doesn't defer.

And we get to choose that version. Daily.

So I'm choosing it today. Even though I'm scared. Even though I doubt. 

Even though part of me wants to play it safe.

I'm choosing Giganti. The big version. The one who shows up.

What are you choosing today?

Real numbers from my own playing bigger journey:

28 days. Daily tracking. One specific habit.

Started at a 5 out of 10. Ended at 8.5 out of 10.

Here's what happened.

I've been working with Level Up Creators as my business partners. They challenged me to get serious about playing bigger. Not just talk about it. 

Actually track it. So, I used the Habit Builder framework. 

I made it specific: "When I feel myself playing small, instead of staying quiet, I will speak up and offer my perspective."

Tracked it every single day for 28 days. Had an accountability partner (thank you Stacy). Had a great coach (Eduardo Briceño) rooting me on!

And my score went from 5 to 8.5 in less than a month (scale of 1-10). 

That's the power of intentionality. Of making playing bigger a daily choice instead of just a nice idea.

You know what else changed?

I find myself showing up completely differently than I ever have.

Not trying to impress. Not comparing myself. Just showing up like I belong. 

Match-making instead of proving. Curious instead of performing.

And the conversations were different. The connections were real. The opportunities that came out of it? 

Better than anything I forced in 25 years of "networking."

That's what happens when you track the daily choice to play bigger.

Here's what I know: Playing bigger isn't about a one-time decision. It's about the daily choice. The moment-by-moment decision to stop deferring and start showing up.

And when you track it? When you measure it? When you have someone holding you accountable?

You actually shift. 5 to 8.5. 
In 28 days.

The math is simple:
⟶ Identify the specific habit
⟶ Make it a When/Instead/I Will statement
⟶ Track it daily
⟶ Get an accountability partner
⟶ Measure the shift

It's amazing what we can do when we're intentional.

So, my question: What would change if you tracked your "playing bigger" habit for 28 days?

What score are you at now? And where could you be?

Over 10 years ago, someone introduced me to the idea that success is driven far more by leading indicators than lagging indicators.

I didn’t totally get it at first.

I grew up in the world of outcomes:

🏆 Trophies
📈 Revenue
🎯 Results

That’s how you measured yourself.

But when I started following the work of James Clear, one line punched me right between the eyes:

“You do not rise to the level of your goals. You fall to the level of your systems.”

And that’s when everything changed for me.

I started shifting from…

❌ Results-first thinking → “Did I hit the number?”

to

✅ Process-first thinking → “Did I do the things that someone who hits the number does?”

That reframe upleveled every part of my life:
	•	my sales career
	•	my leadership
	•	my coaching
	•	my health
	•	my relationships

And today, I get to see the ripple effect of that mindset inside my With Intention cohorts.

Cohort 2 is a perfect example.

Over the last 3 weeks, we’ve been running a habit builder cycle using simple leading indicators:

→ 1 daily habit
→ 1 daily reflection
→ 1 layer of identity (“Who am I becoming?”)

And here’s what happened:

⭐️ Average follow-through rating jumped 86% (3.5 → 6.5)
⭐️ On average, each person took 10.6 meaningful actions
⭐️ 71% journaling consistency
⭐️ 75% buddy accountability adoption
⭐️ Every single person improved. Every one.

None of this comes from chasing outcomes.

It comes from showing up intentionally, one small action at a time.

This is the heartbeat of the With Intention journey.

Identity → Habits → Outcomes.
Not the other way around.

And the beautiful part?

When you get the leading indicators right…
the lagging indicators take care of themselves.

If your team, or your leadership group, would benefit from this kind of transformation, I’m opening a few new seats for Q1.

Send me a note and we’ll explore it together.

Focus on who you’re becoming & 
the results will follow.

Want to know the framework that changed how I think about playing bigger?

It's called the Awareness Matrix. And it's the difference between knowing your strengths and actually living into your brilliance. Here's what most people get wrong:

They work on their strengths. They try to fix their weaknesses. And they wonder why they're still not breaking through.

The real work? It's on the edges.

Your strengths are things you're good at. You know them. Other people know them. They're visible.

Your brilliance? 

That's the thing that comes so naturally to you that you don't even see it. It's like water to a fish. You're swimming in it but you can't see it.

For me, it's listening and building trust. 

Connecting with people. Creating space where they feel safe being real.

I didn't know that was my brilliance for years. 

I thought everyone could do that. One of the best things I did in recent years was take Strategic Coach's approach to Unique Ability. I asked 15 people what they thought my unique ability was.

It was powerful...humbling...and exciting.

Hearing a dozen people say the same thing about what comes easy to me. That's when I realized: This is my brilliance. This is what I'm supposed to give to the world.

Same thing on the other side.

Your weaknesses? You know them. You can work on them. They're visible.

Your blindspots? 

Those are the things you can't see. Your Achilles heel. The thing that's limiting you but you don't even know it's there.

We all have them. 

And we can't fix what we can't see. That's why you need truth-tellers. People who will tell you what you can't see about yourself. 

Here's the other piece my business partners at Level Up Creators taught me: matchmaking.

Stop showing up to meetings trying to impress people. Stop comparing yourself. Stop wondering if you belong.

Just show up curious and interested. 

Ask questions to figure out: Are we a match? Not better. Not worse. Just a match or not a match.

That shift alone will change how you play.

So here's what playing bigger actually looks like: Do the work to identify your brilliance (not just your strengths). 

Ask people. Get coaching. Use assessments. 

Find out what's invisible to you.

Do the work to find your blindspots (not just your weaknesses). Get truth-tellers in your life. Ask the hard questions. 

Be willing to hear what you can't see.

Show up to every conversation asking "are we a match?" instead of "do I belong here?"

When you do this work, playing bigger stops being about confidence or ego. It becomes about clarity.

You know what you bring. You know what to watch out for. And you show up accordingly.

Where do you need to do the work? On your brilliance or your blindspots?

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The Battle

Stacy Bishop

Jon Giganti

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The Battle

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Jon Giganti

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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);}Stacy Bishop's LinkedIn Performance

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