Santi & Co (WithSanti.com)

I am an executive coach to founders, entrepreneurs, and leaders growing their businesses and navigating key transitions in life and work. I offer 1:1 coaching and three types of peer groups I curate and facilitate: Startup Founder Peer Group, HoldCo Owner Peer Group & Leaders in Transition Peer Group.

Owner & Executive Coach

Sabbatical

15Five

15Five is a human-centered performance management platform that creates effective managers, highly engaged employees, and top-performing organizations. From engagement surveys and 1-on-1 tools to performance reviews and OKRs, 15Five is the most complete solution that combines software, education, and community to develop successful managers and unlock peak employee performance. Built using the Positive Product Design™ method, 15Five is the only platform that offers software aligned to the latest positive psychology research. Through it’s HR Superstars community and podcast, 15Five aims to empower every leader to create highly engaged, high-performing organizations by helping people become their best selves.

15Five Senior Executive

Emplify - Employee Engagement

Emplify is on a mission to help organizations unlock human potential so employees can do the best work of their lives. While US companies spend a staggering $720 million annually on employee engagement, measuring the return on this investment is often derived from outdated annual surveys or ad-hoc polls. Emplify’s unique agile engagement platform leverages both quantitative and qualitative employee feedback through hassle-free survey administration and analysis to provide visibility across the entire organization to leaders. Rooted in the belief that yearly surveys alone are no longer effective to create highly engaged cultures, Emplify’s agile measurement framework combines surveys with quarterly check-ins and pulse polling to uncover the core issues behind symptoms like high turnover, low productivity, and poor innovation, enabling leaders to make data-driven decisions that bridge people and profit. Learn more at emplify.com.

CEO & Co-Founder

Bluebridge

Bluebridge helps organizations communicate and engage with their internal audience (employees) and external audiences (customers, visitors, members, etc) through a mobile app engagement platform. Corporations use the Bluebridge Mobile Engagement Platform to communicate internally with their employees and many, like Conventions & Visitors Bureaus (communicate with visitors) and Churches (communicate with their congregations), leverage the Bluebridge mobile app engagement platform to communicate with their external audiences. 

With interactive app content features and world-class, highly personalized push notification messaging capabilities, the Bluebridge platform empowers organizations to grow their organizations by engaging their audience through branded, compelling, and easy-to-use native mobile apps. With over 500 mobile apps published in various app stores and serving hundreds of customers around the world, Bluebridge is headquartered in Indianapolis, IN where the team of over 30 passionately builds the future of mobile communication and engagement. Learn more at gobluebridge.com.

CEO & Founder

U.S. Music Camps

Founded and directed entrepreneurial venture; designed and implemented marketing plan including website with e-commerce integration, direct mail, email marketing, and print media advertising campaigns.

Hired and led staff of 20 and served over 120 customers.

Developed plan to expand to three locations in 2009 and executed the plan in the summer of 2010 successfully to expand into two states.

Founder

ExactTarget

Lead out ExactTarget's competitive intelligence programs and strategy. Publish the weekly CI Newsletter as well as support the sales organization in competitive situations.

Competitive Intelligence

Worked with Partners Manager to develop and nurture ExactTarget's relationships with key partners in Asia-Pacific such as: Microsoft, Adobe Omniture, Webtrends, Salesforce.com, BazaarVoice, and others.

As part of the partnership team, met over 150% of the sales target for Q2 2011 in channel revenue, trained sales staff on on how to leverage partners to close more business, and coordinated ExactTarget's presence at several partner events: Webtrends Engage 2011 (Sydney) and Dreamforce 2011 (Sydney).

Asia-Pacific Partnerships - Sydney, Australia

Specialized in competitive intelligence in the Product Marketing.

Drove the creation of the Competitive Insight Newsletters, with all of ExactTarget's worldwide employees as the audience. The newsletter included analysis and positioning on competitor's actions in the industry.

Was brought in by the corporate sales team to aid in engaging  a prospect in an international opportunity. Built rapport and overcame objections to close a significant international deal in Spanish.

Product Marketing 'Slingshot'

University Storage, LLC

Created entrepreneurial venture to meet need of college students; incorporated business in the state of Indiana; developed a business plan and oversaw a marketing blitz that resulted in more than 100 customers in the first month.

Hired and trained a sales team of 12 students and developed pricing structure and commissions.

Exited in 2010, selling all interests to University Storage's cofounder.

Founding Partner & President

I am an executive coach to founders, entrepreneurs, and leaders growing their businesses and navigating key transitions in life and work. 

As a former founder and CEO myself, I started, built, and sold several successful, high-growth companies now worth almost $100M, hired nearly 200 employees, and was able to positively impact millions of lives. I now draw on my 10+ years of practical experience to help clients achieve transformational growth and improved business results.

I’m also the co-author of “Agile Engagement” (Wiley, 2016) and a national keynote speaker and columnist on topics like innovation, enterprise growth, employee engagement, org culture, and workplace strategy. My ideas have been featured in publications including Inc., Forbes, Fast Company, and the Indianapolis Business Journal.

Other awards and accomplishments include:
- Indiana Latino Businessman of the Year (2016)
- Indianapolis Business Journal 40 Under 40 (2015)
- Inc. Magazine's 30 Under 30 (2013)
- Whitehouse.gov "Champion of Change" - Obama administration (2013)
- Techpoint "Young Professional of the Year" Mira Award Winner (2013)
- IndyStar "Rising Star" Award Winner (2013)

One of the most dangerous assumptions in business (that I learned the hard way): 

Your market intuitively understands your value proposition. 

Spent an entire summer cold-calling prospects for a mobile app idea.

Zero sales. 

Not because the idea was bad, but because I was asking busy executives to imagine value they'd never experienced.

So I pivoted from persuasion to proof-of-concept.

Since this was 2011, I built a politically-neutral "Occupy Wall Street" newsfeed app.

10,000+ downloads in weeks.

Created a paid version for $1.99.

Then the Super Bowl came to Indianapolis.

I saw opportunity everywhere, which turned into:
- Indy Transport
- Indy Eats
- Indy Nightlife
- We Love Indy

Four apps. One massive event. Real traction.

Finally, the Kokomo Visitors Bureau called.

They'd seen my work and wanted their own app.

They became Bluebridge's first customer.

The framework that emerged:
Assumption → Prototype → Measurement → Iteration

NOT: Research → Plan → Build → Scale

For sophisticated operators, this means:
👉🏽 Instead of presenting strategic initiatives to your board—pilot them.
👉🏽 Instead of proposing new customer segments—serve a few and measure retention. 
👉🏽 Instead of debating team structure changes—test new models with willing volunteers.

The meta-insight: Your next breakthrough likely exists in the gap between what you're PLANNING to validate and what you could ACTUALLY validate this week.

What business assumption could you test now with a prototype instead of a presentation?

Santiago (Santi) Jaramillo

Executive Coach to Founders & Leaders (3X Exited CEO & Founder). AI Consulting.

My Bluebridge co-founder Adam Weber and I celebrating the launch of several tourism mobile apps for the 2012 Indianapolis Super Bowl at Lucas Oil Stadium

At 22, I found myself sweating through my dress shirt in my co-founder’s living room, pitching his wife on our startup, Bluebridge.

Cara Weber, AIA had just asked the question I was not prepared for:

“Will my kids have health insurance from Day 1?”

I was still on my parents’ plan. Had no clue about how to set up health insurance benefits.

But I knew I could figure it out.

So without hesitation, I said: “Absolutely. Not a single hour of coverage will lapse.”

That “fake it till you make it” moment led to:

• Adam Weber joining as my co-founder
• Building Bluebridge to millions in recurring revenue  
• Raising millions in VC funding
• Growing to 40 employees
• Becoming the world’s largest tourism app platform

Yes—vulnerability matters. Your team needs to see you own your mistakes and be human.

But there are moments when the most authentic thing you can do as a leader is act more confident than you feel.

But the difference between confidence and all-out delusion?

Delusion says: “I already know everything.”

Confidence says: “I don’t know how, but I’ll figure it out."

Your team doesn’t always need to see you sweat.

They need to see that you believe the mountain can be moved—even when you’re still figuring out where to find the shovel.

Learning in real-time and owning your ability to solve problems isn’t being “fake.”

It’s being a leader.

How do you decide when to project confidence vs. show vulnerability?

What’s the boldest “I’ll figure it out” promise you’ve ever made?

Unpopular opinion: Giving advice is lazy leadership.

Most CEOs yearn to be told the "right answer.”

That's exactly why great coaches don't.

Carl Jung was right: “The shoe that fits one person pinches another; there is no recipe for living that suits all cases.”

Advice:
- Assumes situations are universal
- Gives you my answer to your problem
- Creates dependency on external validation
- Fast but shallow
- Makes you feel helped in the moment

Coaching:
- Assumes situations are unique
- Helps you find your answer to your problem
- Creates increased capacity for clearer thinking
- Slow but deep
- Makes you feel more capable long-term

When a CEO asks “What should I do?” I usually respond with:

- “What are the options you're considering?"
- “What information are you missing?”
- “What would happen if you did nothing?”
- When has a similar situation worked out well for you?

The answers are already inside you. I'm not doing my job as a coach if I take the opportunity to discover them away from you.

When I was a kid, lobster hunting with my dad meant one thing: tunnel vision.

Every muscle tense. Senses heightened. Zero peripheral awareness.

Oh, I caught lobsters (and got much-needed braces). But I missed everything else.

15 years later, I found myself in "hunter mode" again.

But instead of a snorkel and mask, I was donning a dress shirt and blazer.

Always chasing the next deal, the next milestone, the next win.

And I was ravenously exhausted.

Here's what I've learned since building and selling three companies:

24/7 "Hunter Mode" is unsustainable.

Many celebrate the leader who works 80-hour weeks and never takes vacation.

But constant hunting creates blind spots.

You miss market shifts. Team burnout. Strategic opportunities. The coral reef around you while you're tunnel-focused on the lobster.

The best leaders operate like skilled divers.

They know when to hunt with precision:
- Closing critical deals
- Managing crises
- Executing time-sensitive strategies

And when to explore what's possible:
- Scanning for new opportunities
- Building relationships without agenda
- Reflecting on long-term vision
- Recovery and enjoyment of life beyond work

Hunters focus intensely but exhaust quickly.

Explorers stay curious but lack swift action.

Great leaders flow between both modes intentionally.

Now I prioritize. I breathe deeper. I "switch off" routinely.

I notice the coral while still tracking the lobster.

Success isn't about constant intensity.

It's knowing when to dive deep and when to surface for air.

Right now, in your leadership:

Are you hunting or exploring? Or both?

And more importantly—how is it serving you?

8-11 PM used to be my second workday.

When inspiration (or necessity) strikes at night, it can be intoxicating.

But it comes with a cost. Sometimes that cost is worth it. Often it’s not.

Working late usually meant: 
• Racing work thoughts as I try to fall asleep
• Dreaming about work all night 
• No/little mental recovery time 

The key insight:

I needed unscheduled time DURING the day, not a packed calendar that forces passion or admin work late into evenings.

Creativity compounds when it has space to breathe and recover.

How do you approach switching off from “work mode”?

Plot twist: The most authentic leaders I know aren't just "being themselves."

They're being their best selves.

Here's the difference, and why it matters:

In my second startup during hypergrowth, I hit a wall.

My natural patterns weren't scaling with the business.

I was making decisions from stress instead of strategy.

Reacting instead of responding.

Running on caffeine and adrenaline instead of sustainable energy.

My team needed a CEO who could handle complexity and pressure.

I was giving them someone who was barely handling his own life.

That's when I learned a hard leadership lesson:

Your business will only grow as fast as you do.

So I started doing “the work:”
✅ Sleep became non-negotiable. 7+ hours, every night.
✅ Morning routines to center myself before the chaos.
✅ Regular exercise to manage stress and think clearly (hot yoga was 🔥).
✅ Mindfulness practices to catch reactive patterns.

The business transformed as I did.

Better decisions. More sustainable energy. Stronger relationships.

After three exits and 1,500+ hours coaching senior leaders, I've seen this pattern repeatedly:

High-growth companies require leaders who commit to high-growth mindsets.

Not just strategy and systems.

But rather sleep, nutrition, emotional regulation, and self-awareness.

Your "authentic self" isn't who you are right now.

It's who you're capable of becoming.

And your team is counting on that evolution.

What's one area of inner work that transformed your leadership effectiveness?

Unpopular opinion: Most leaders make executive decisions 3-6 months too late.

I see this pattern constantly with the executives I coach:

What they think they're doing:
- Giving people a chance to improve
- Being supportive and developmental
- Showing loyalty to their team

What's actually happening:
- Eroding trust with other high-performing senior leadership
- Sending mixed signals about performance standards
- Burning their own credibility 

The real cost isn't just underperformance.

It's the opportunity cost of what your organization could accomplish with the right person in that seat. 

Imagine your highest-performing leader in the company (let’s call them “Amy”). 

Now, imagine having an Amy-level leader in the seat of the underperformer. What could you and the team accomplish with someone truly world-class in that role? Doesn’t the mission and team deserve an “Amy” in every leadership seat?

One of my favorite decision-making frameworks for leadership personnel decisions?

Netflix’s “Keeper Test:”

If this person were to resign tomorrow, would you fight like hell to keep them?

If the answer is “no,” stop hoping for a miracle, and start planning for the transition.

One of my CEO clients said something that stopped me cold:

"My biggest strength has become my biggest weakness."

He was talking about leadership competence.

His ability to see solutions quickly.

To organize resources and people.

To get things done efficiently.

In business? This skill made him tens of millions.

In his personal life? It was killing his relationships.

His wife felt managed, not partnered.

His kids felt fixed, not heard.

Here's the paradox of high-achiever psychology:

The skills that create professional success can create personal struggle.

We become so good at solving problems that we forget some problems aren't ours to solve.

We become so efficient at making decisions that we forget some decisions aren't ours to make.

The solution isn't to become less competent.

It's to become more intentional about when and how we use our competence.

Sometimes leadership means stepping back.

Sometimes strength means letting others struggle.

Sometimes the best thing you can do is ask:

"How can I support without taking over?"

The people in your life don't need you to fix them.

They need you to see them.

To trust them.

To love them without an agenda.

That's one of the hardest skills for high achievers to learn, and perhaps the most important.

A question that's been on my mind: Why do we expect leaders to scale businesses without scaling themselves?

We rightfully obsess over growth metrics, market strategies, and operational systems.

But we often ignore the most critical factor: the leader's capacity to grow in lockstep with the demands of the role.

Here's what I've learned after three exits and coaching 20+ leaders:

A business will hit a ceiling at exactly the point where its CEO stops growing.

Not because they lack skills.

But because they lack the self-awareness and inner work to develop those skills.

The leaders who break through aren't just learning new tactics.

They're doing the deep work:
- Building routines that support sustainable energy (sleep, exercise, nutrition)
- Developing emotional regulation under pressure
- Creating space for reflection and strategic thinking
- Identifying and changing limiting patterns and beliefs

This inner work isn't "soft skills."

It's the hardest work you'll do as a leader.

And it's what separates leaders who plateau from those who scale.

So here's my question:

What's one area of inner work (sleep, emotional regulation, self-awareness, habits) that you know would improve your leadership?

Drop it in the comments—let's normalize talking about the real work of leadership.

The hardest lesson I learned as a 3x founder: assumed understanding is the enemy of execution.

I used to think being a good leader meant people would just "get it."

So I'd assume everyone was on the same page as me.

Skip the follow-up conversations.

Then get upset when people delivered work that didn’t meet my expectations.

Finally, after the umpteenth time around this circuit, I realized something:

I was having conversations in my head that never left my mouth. I was asking the team for things without giving them context. I was making decisions and then forgetting to tell anyone.

George Bernard Shaw said it best, "The single biggest problem in communication is the illusion that it has taken place."  

Clear communication isn't about being articulate.

It's about ensuring the message was received and understood.

It's not about what you say—it's about what they understand.

Now I coach CEOs who sometimes struggle with the same thing.

Smart leaders who think clarity means saying it once.

Sending the email. Making the announcement. Assuming understanding.

But your team doesn't need you to communicate perfectly.

They need you to communicate completely and repeatedly.

The most successful leaders I work with have mastered this:

They don't just deliver messages—they confirm receipt.

They ask: "What did you hear me say?"
They check: "How does this land with you?"
They verify: "What questions do you have?"

Because in leadership, assumed understanding is the enemy of excellent execution.

Leaders: What is the hardest communication lesson you’ve learned?

A massive reality check for everyone investing in AI:

75% of the C-suite think their AI adoption is “very successful.”

Only 45% of employees agree. 

(Source: WRITER’s 2025 AI Survey)

The missing piece I’m seeing:

Strategic vision communication + systematic upskilling.

Because here's the truth:

AI requires the kind of intentional change management most organizations have never attempted.

AI  ≠ software deployment

You can't train someone out of old habits with a two-hour workshop.

You need sustained culture change.

So here's my question for you:

Leaders: How are you personally driving AI literacy in your organization?
Employees: What would make you feel more confident about AI at work?

The disconnect is real, but it's not permanent.

It just requires leaders who are willing to own the change process.

I see this fear paralyze so many leaders: 

The fear of being seen as "too important" for the day-to-day work they ought to delegate.

The anxiety that stepping back means stepping away from their people.

"What are you afraid will happen if you're not as connected internally?" I asked my client the other day.

His answer: "People will think I don't care about them anymore."

But here's what I've learned coaching 20+ executives:

Your team doesn't need you in every meeting.

But they DO need your clarity in every decision.

Your evolution as a leader isn't about becoming less involved.

It's about becoming more strategic about where you add unique value.

When you communicate WHY and WHERE you're shifting your focus, something magical happens:

Your team doesn't feel abandoned. They feel trusted.

They see a leader confident enough in their abilities to focus on what's ahead.

The best CEOs I work with have learned this truth:

Stop measuring your leadership by how busy you are.

Start measuring it by how capable your team becomes without you.

The goal isn’t to be indispensable.

It's to make your vision so clear that it guides decisions even when you're not in the room.

So here's my question for you:

If you freed up 10 hours this week by delegating better, what would you focus on instead?

We're asking Stone Age brains to work in Space Age environments, and wondering why everyone's kind of burned out.

Think about it:

Our ancestors spent 12+ hours outdoors every day. Moving. Problem-solving in natural light.

Today, we lock our teams in windowless conference rooms under fluorescent lights for hours, then wonder why productivity tanks at 2 PM.

I now schedule walking catch-ups and networking meetings outdoors whenever possible.

The difference is noticeable. 

Not just energy levels (though those improved).

Walking meetings produce different conversations entirely.

Something psychological shifts when the body is in motion instead of sitting still.  

People open up differently. Ideas flow better. Problems get solved faster.

The data backs this up: Stanford research shows walking increases creative output by 60%.

But most leaders ignore biology in favor of "best practices."

Start designing WITH human nature, not against it:
- Move your next 1:1 outside
- Host brainstorming sessions near windows or outdoors
- Take difficult conversations for a walk
- Ask your team where they feel most creative

Any fans of walking meetings out there?

I stared at the conflicting data on my screen, my anxiety rising.

Our customer acquisition costs had doubled. Retention was slipping. The executive team was pointing fingers.

How had we veered so far off course?

Three months earlier, I'd proudly implemented "proper management structure." 

Hired experienced executives. Created clear reporting lines. Stepped back to be "strategic."

I followed the scaling playbook perfectly.

And it was killing everything special about our company.

This painful lesson taught me what business schools don't: 

Founder-led companies are different. They thrive on a unique energy that conventional management wisdom often extinguishes.

In founder-led companies: 
• Decision velocity matters more than decision perfection 
• Cross-functional innovation happens through unexpected collisions 
• Culture emanates from the founder's authentic presence & creativity

When Brian Chesky followed traditional scaling advice at Airbnb, the company nearly imploded. 

Only by returning to "founder mode" – deeply connected to product, customers, and culture – did they recover their magic.

I've now worked with 20+ founder-CEOs navigating this exact transition.

The successful ones don't abandon their unique strengths. They evolve them:

✔️ Maintaining product intuition while building scalable processes
✔️ Preserving customer obsession while expanding market reach
✔️ Infusing their values through the organization without bottlenecking decisions

Your unique founder energy isn't something to "grow out of." It's one of your competitive advantages.

What founder superpower have you suppressed in the name of "proper management" that your company may need right now?

Your calendar reveals more about your priorities than your mission statement.

A CEO client just told me she implemented "No Meeting Wednesdays."

Her exact words: "It wasn’t easy, but it seems to be working."

Before: 
• Back-to-back meetings from 9-5
• No time for strategic work 
• Consistently working late nights and weekends 
• Constant task switching between investor calls, customer calls, and internal team meetings 
• Self-blame: "Why am I not getting things done?"

The breakthrough moment: She stopped blaming herself—and started redesigning her structure.

After implementing Wednesday boundaries: 
• 6+ hours of uninterrupted focus time 
• Space for strategic thinking 
• Better preparation for all other meetings 
• Energy sustained throughout the week 
• Tuesday thinking shifted from "it's only Tuesday" to "relief is coming tomorrow"

The real test came when a client requested a Wednesday call.

She almost said yes. 

Then she protected the boundary and suggested Thursday.

If your schedule doesn't align with what matters most, you're not managing your time—your time is managing you.

Sometimes the most confident move a leader can make is to signal, “I’m not available right now, because I’m working on what matters most.” 

When everything feels urgent, the problem isn't your workload. 

It's your focus and your boundaries.

Question for you: What's one calendar boundary that could transform your week?

The transition from "inside CEO" to "outside CEO" is one of the most misunderstood leadership evolutions.

Last week, one of my CEO clients faced a brutal truth:

His team thought he was "checking out."

Missing meetings. Less face time. More external events.

The reality? He was evolving his role exactly as the business needed.

Most founders resist this shift for three psychological reasons:

1. Guilt - "My team will think I don't care about them."
2. Control - "What if everything falls apart without me?"
3. Identity - "Who am I if I'm not needed in every important meeting?"

But many businesses’ evolution depends on the CEO evolving through three phases:

Phase 1: Firefighter CEO
You ARE the business
Every decision flows through you
Success = your personal output

Phase 2: Orchestra Conductor CEO
You're IN the business
You conduct but don't play every instrument
Success = team output

Phase 3: Architect CEO
You take the business OUT into the world
You foster external partnerships, vision, and strategy
You curate and develop the team to execute the strategy
Success = market position

The problem:
Most teams only see Phase 1 as "real leadership."
When you evolve to Phase 3, they may think you're disengaging.
So my client sent one email (and 5 minutes in an all-team) explaining his evolution.

The response?

His team felt MORE connected to him, not less.

They understood their CEO was thinking 10 years ahead, versus 10 minutes.

What phase are you in? And more importantly, does your team know?

Want to expose fear and confusion in your company?

Ask: “Who’s using AI, and for what?”

Watch what happens:

Marketing brags about cutting hours to minutes.

Finance looks lost.

Sales asks if it’s even allowed.

IT smirks—they’ve been using it for months.

This isn’t innovation—it’s fragmentation.

Every department moving in different directions. No shared definition of “good” AI use.

The AI fluency gap isn’t about skills—it’s about confidence + clarity.

The winners?

They align on when, where, and why to use AI.

Then they scale it across the org.

What’s the biggest AI win or fail you’ve seen in your company so far?

FearConfusionAI

I ask almost every C-suite exec I coach: "On a scale of 1-5, how are you feeling at work? How about in life?"

Common responses:
"Work: 4. Life: 2."
"Work: 5. Life: 1."

Here’s what I almost never hear:

"Work: 4. Life: 4."

The pattern is brutal.

Lots of high achievers sacrifice everything to keep work at a "5."

And we tell ourselves it's temporary.

"Once we close this round…"
"After we hit $50M in revenue…"
"When I hire the next exec…"

But there’s always another milestone to chase. Another emergency to solve.

Meanwhile:
- Fitness deteriorates
- Relationships atrophy 
- Energy wanes
- Joy fades

But here’s the truth: you don’t have to choose between “winning at work” and “having a life.”

Your life energy is your highest-return business asset.

Protecting it isn't selfish.

It's strategic.

I learned this the hard way. 

I spent my 20s as a "Work: 5, Life: 1" CEO.

Now I help leaders avoid that same trap.

Protecting your energy isn’t soft. It’s the most aggressive growth strategy you’ll ever deploy.

The most successful leaders I coach?

They protect their energy like they protect their P&L.

They understand that sustainable success beats unsustainable heroics.

What’s one system, habit, or hire that gave you more of your life back? 

What's something that helps you reconnect with more vitality and aliveness in your work and life?

Having "too many good ideas" isn't always a superpower.

It can be an Achilles Heel.

Everyone celebrates the visionary founder—the one who sees opportunity everywhere.

I was that founder.

At Bluebridge, we had 5 different market strategies early-on:
Tourism apps
Church apps
University apps
Sports team apps
Corporate apps

We called ourselves "the WordPress for mobile apps."

Sounds impressive, right?

Here's what that ACTUALLY meant:

Three salespeople chasing 5 completely different audiences.

Totally different messaging, buyers, and go-to-market plays.

Little alignment. Constant resource battles and focus challenges.

The hard truth:

What got you HERE (spotting opportunities) won't get you THERE (executing them).

Visionaries see possibilities.

Operators create focused realities.

The best leaders know when to infuse new ideas to spark growth—and when to double down on the core, protecting it from distractions.

Your ability to say no to good ideas is what allows you to say yes to great outcomes.

How do you decide when to pursue an idea vs. park it?

What’s one "good" opportunity you passed on—and are glad you did?

What does AI fluency look like for someone who lives in Salesforce vs. someone who lives in Excel?

Every team needs to be fluent in AI—but in different dialects. 

So I created a matrix that explains.

Match AI training to the role. Match the tools to the problems. Match the success metrics to what actually matters for that job.

Taplio

Santiago (Santi) Jaramillo's Linkedin Analytics

's Best Posts (last 30 days)

Want to drive more opportunities from LinkedIn?

Taplio

.css-1jgreyo{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;}Santiago (Santi) Jaramillo's Linkedin Analytics

's Best Posts .css-qqfgvy{font-size:var(--chakra-fontSizes-md);}(last 30 days)

Want to drive more opportunities from LinkedIn?

Santiago (Santi) Jaramillo's Linkedin Analytics

's Best Posts (last 30 days)