Arrival01 / 06
Tamarindo · Pacific Coast
The moment your phone finally stops buzzing
Warm air. Clear calendar. For the first time in months you're not putting out fires, you're thinking about what's possible.
3 Years Sold OutApril 26–29, 2027 · Tamarindo, Costa Rica
Your Next Breakthrough Won't Happen Alone.The Premier AI, Automation & HighLevel Founder Experience
Four days. 100 founders, agency owners, AI innovators and business leaders in one intentionally small room on the Pacific coast.
Hosted by Kaitlyn Lemus Portillo · Sponsored by HighLevel
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Watch why founders fly across the world for this room
✓Hosted by Kaitlyn Lemus Portillo✓Sponsored by HighLevel✓3 Years Sold Out✓Limited to 100 Entrepreneurs✓April 26–29, 2027
The truth nobody says out loud
You can learn almost anything online.
- How to generate leads.
- How to build funnels.
- How to automate your business.
- How to use AI.
- How to scale.
Information has never been more accessible.
Yet the entrepreneurs building the fastest-growing companies in the world all have one thing in common...
They didn't build them alone.
They found:
- ✦The right people.
- ✦The right mentors.
- ✦The right partners.
- ✦The right conversations.
- ✦The right room.
That's exactly why Kicking SaaS Summit exists.
For four days, 100 founders, agency owners and AI innovators come together on the Pacific coast to learn, collaborate and create opportunities that continue long after the event ends. No convention center, no endless pitches, no anonymous back row. Just an intentionally curated experience built to help ambitious entrepreneurs think bigger and move faster.
Because the biggest opportunities rarely happen on stage.
They happen in the conversations before breakfast...
- During lunch...
- Walking on the beach...
- Sharing ideas over dinner...
- Or watching the sunset beside someone who completely changes the way you think.
The beach is unforgettable.
The speakers are world-class.
But the people you meet may become the most valuable part of your entire year.
If you're serious about building what's next...
We'll see you in Costa Rica.
Why this exists
Why Kicking SaaS Summit exists.
There are thousands of business conferences.
Hundreds of AI events.
Countless marketing summits.
Most of them promise the same thing: more information, more strategies, more tactics.
And while information matters, it has never been easier to find. What has become increasingly difficult to find is:
- ✦Genuine connection.
- ✦Real conversations.
- ✦Honest feedback.
- ✦Meaningful relationships.
This isn't about filling seats. It's about filling a room with people who genuinely want to see one another succeed.
01
Speakers who don't disappear.
No backstage curtain. They answer questions, stay after their sessions and sit beside you at dinner.
02
Introductions that become partnerships.
Conversations continue long after the sessions end. Ideas become businesses. Competitors become collaborators.
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Entrepreneurs who stop building alone.
The kind of people who challenge your thinking instead of simply agreeing with you.
04
A room, not a crowd.
We're not trying to be the biggest event in the industry. We're trying to be one of the most valuable.
Every business has turning points.
- Sometimes it's launching a product.
- Sometimes it's hiring the right employee.
- Sometimes it's signing the biggest client you've ever had.
And sometimes it's deciding to get in the right room.
You never know which conversation will change your business. You only know one thing: you have to be there when it happens.
This is more than four days.
It's the beginning of relationships that continue long after your flight home. It's a reminder that success isn't meant to be built alone.
It's proof that your next level often starts with a simple introduction, and our commitment to creating one of the most welcoming, inspiring and valuable founder experiences in the world.
That's why we do this. Every single year.
Your host
Kaitlyn Lemus Portillo
Meet your host
Built around connection, not another conference.
Entrepreneur.Founder.Builder.Community creator.
For years, Kaitlyn has helped entrepreneurs build businesses powered by automation, AI and systems that create more freedom.
She's built companies, spoken on stages, served thousands of business owners and watched one truth reveal itself over and over again.
The biggest breakthroughs rarely happen because someone learns one more strategy. They happen because someone meets the right person.
That's the vision behind Kicking SaaS Summit. An event where conversations matter just as much as presentations, and where ambitious entrepreneurs leave with more than pages of notes.
- ✦Relationships.
- ✦Partnerships.
- ✦Ideas.
- ✦Momentum.
- ✦And memories they'll never forget.
If this is your first Kicking SaaS Summit, welcome. We're honored you're considering joining us.
If you're returning, welcome home.
The experience
This isn't just another conference. It's four days you'll talk about for years.
Founders from around the world are already arriving. Some are running seven-figure companies. Some are building the next breakthrough in AI. Within minutes, you're all speaking the same language: growth, leadership, freedom, opportunity.
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Day One02 / 06
Check-in · Sunset reception
Welcome to Costa Rica
Not registration. The beginning of your experience. Shake hands with people you've followed online for years and watch the sun disappear into the Pacific.
Mornings & Evenings03 / 06
Daily · Beachfront · Open to all attendees
Yoga, sound frequency and PEMF recovery
Between sessions, reset your body and mind. Sunrise yoga, sound frequency healing and PEMF therapy are available every morning and evening, no experience needed. Costa Rica slows life down so the conversations here stay unhurried, authentic and real.
Day Two04 / 06
Keynotes · Workshops · Panels
Learn what's working right now
Every speaker is actively building. No theories, no recycled decks. Real lessons you can put to work the moment you get home.
Day Three05 / 06
Breakfast to late night
Bigger conversations
Breakfast turns into brainstorming. Lunch becomes collaboration. Coffee becomes consulting. You're no longer meeting strangers, you're building relationships.
Day Four06 / 06
Beachside dinners · Founder afterhours
You leave different
Not because someone motivated you. Because someone challenged you. You board your flight home with more than inspiration. You leave with momentum.
Why Costa Rica
We could have rented another ballroom.
Costa Rica changes people. It slows life down and creates space to think, to reflect, and to reconnect with why you started building in the first place.
Somewhere along the way, many entrepreneurs accidentally build businesses that own them. This isn't an escape from your business. It's a reminder of why you built it, because business should create freedom.
One year from today you won't remember another webinar. You'll remember the sunset, the dinner where ideas turned into action, and the conversations that gave you clarity.
April 26–29, 2027 · Guanacaste · 100 seats total
Reserve Your Seat →The room speaks
Don't take our word for it. Listen to the people who've been in the room.
Every year we ask ourselves one question: would people come back? The answer has been overwhelmingly clear. The most meaningful feedback isn't about the venue, or the weather, or even the speakers. It's about how people felt, the relationships they built, and the momentum they carried home.
0x
Sold out, years running
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Founders per year, intentionally
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Countries represented
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Days on the Pacific coast
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The speakers were phenomenal — so many takeaways and so much knowledge shared. Tamarindo is beautiful, the locals are lovely, and I'll be back to show my daughter this side of the world.
Hayley Brown
AI Specialist
"
Kicking SaaS Summit in Costa Rica will be a before-and-after story for my business. I met incredible humans doing mind-blowing things and helping people in so many ways.
Anna Andrea
Event Strategist
"
Watching Danny speak about funnels, AI and automations was incredible — but what really stayed with me were the conversations. Powerful stories of strength, wisdom and perspective.
Elizabeth Clarke
Creative Director
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Being in that space, surrounded by incredible people doing meaningful work, reminded me that growth rarely happens inside our comfort zones.
Stefanie Kim
Marketing Automation Specialist
"
An incredible way to spend a milestone year — new culture, new food, sun, surf, family and friendship. A lot of learning and relationship building behind the scenes too.
Jason Townsend
Senior Integrator and Operations Lead
"
Experiencing the ultimate pura vida vibe in Tamarindo, empowered by incredible insights on GoHighLevel from phenomenal speakers at a truly phenomenal summit.
Amber Farrow Taggard
Entrepreneur
More than 100 entrepreneurs. One community.
Agency owners. Software founders. Marketing leaders. AI innovators. Consultants. Operators. Creators. Investors. Business owners from dozens of industries with one thing in common: a desire to keep learning and surround themselves with people who inspire them to become better.
The summit may last four days. The relationships last much longer.
This is why we keep it small.
Could we sell thousands of tickets? Probably. But we want attendees to recognize faces, remember names, continue conversations, build trust and feel like they truly belonged.
That doesn't happen in a crowd of thousands. It happens in a room of one hundred. Sometimes success isn't one big moment. Sometimes it's one introduction.
Video stories
Hear it from the room.
Event highlights
Three years of paradise.
The breakthrough year · Tamarindo
Oceanfront dinner with the whole room
Long-table dinner in the jungle
Poolside afterparty under the lights
Late-night cheers with the crew
Hands-on workshop, phones out, room engaged
Founders working the exercise in real time
Live Q&A with the room fully locked in
Nipun Syal on stage, breaking down the playbook
Complexity Kills Scale · thinkrr.ai
FAQ WebChat, live founder walkthrough
Full room, sharp frameworks
Founder mixer under the terrace lights
Perspective from the room, live workshop
The Real Problem · keynote breakdown
Mixer cheers with the HighLevel crew
Terrace bar conversations after sessions
Between sessions, the room keeps moving
Live workshop · room locked in
Costa Rica color, style, and energy
Speaker lineup banners outside the convention center
Private chef stations at the night party
Sunset terrace mixer, drinks and conversation
Live teardown, speaker working straight from his phone
Workshop talk, full room focused on the point
Laptops open, room fully engaged
Side-angle audience view, notes and cameras rolling
Poolside trophy moment with the thinkrr.ai crew
Full house, eyes on the keynote
Front-row focus, laptops open
Jungle sound bath, crystal bowls and palms
Keynote on the roadmap to 10M installs
Late-night mixology under the string lights
Founder masterclass, room locked in
2026
Photo coming
More moments coming
Swipe →
Where you stay
Two locations. One unforgettable week.
Premium attendees stay at a beachfront resort in Tamarindo. Ten VIPs disappear into a private Marriott estate inside Hacienda Pinilla.
General Admission
Beachfront Resort
Playa Tamarindo · Guanacaste
Iconic beachfront. Steps from the surf.
Beachfront Resort, Tamarindo
Premium GA guests stay at one of Costa Rica's most iconic beachfront resorts, five-star tropical pools, palm-lined gardens, and direct access to Playa Tamarindo's golden sand at sunset.
- Direct beach access
- Multiple pools & swim-up bars
- Sunset ocean views
- On-site dining & spa
- Walk to Tamarindo nightlife
- Local drivers available on arrival
- 4★
- Beachfront Resort
- 60 min
- From Liberia Intl. (LIR)
VIP
VIP Residence
Hacienda Pinilla · Pacific Coast
A private 10-founder estate inside Marriott's gated reserve.
Villa Tranquila, Hacienda Pinilla
Only 10 VIPs accepted (each may bring a +1). The entire Villa Tranquila estate is taken over for the summit, private chef, private beach club, four pools, golf carts on call, and the kind of access most travelers will never see.
- Only 10 VIPs · +1 included
- Private chef · curated menus
- Private beach & beach club
- 4 pools & relaxation areas
- Golf carts on the estate
- Marriott Homes & Villas property
- 10
- VIP seats · limited
- 4,500 acres
- Gated Hacienda Pinilla reserve
The lineup
Meet the founders, operators and innovators shaping what's next.
6 confirmed · more dropping weekly
Learn from the people who are building it, not just talking about it.
Every person we invite to the Kicking SaaS Summit stage is actively growing a company, solving real problems, serving real customers and navigating the same challenges you are. They aren't speaking because they're famous. They're speaking because they've earned the right to teach what they're doing today.
You'll hear their wins, their failures, their lessons, and the strategies they would use if they had to start over tomorrow.
Filter by track
★ Opening
"How to build a sold-out movement, not a conference"
3x sold out · 47 countries
Founder & Host
Kaitlyn Lemus Portillo
Freedom Mastery Events
View profile →
★ Keynote
"AI video and organic distribution that compounds every month"
1.5M+ followers · 500M+ views
Founder & CEO
Austin Armstrong
Syllaby.io
View profile →
"The state of the agency stack in 2027"
Platform powering 100k+ agencies
Partner Keynote
HighLevel
HighLevel
View profile →
"Inside the white-label ops playbook powering HighLevel's top partners"
Founder
Dakota Routh
White Label Suite
View profile →
"From service to scalable: productizing what you already sell"
Founder
Danny Clarke
Easy Peasy Funnels
View profile →
"Simulating your way to a self-running sales machine"
Founder · MYCRMSIM
Founder
Gary Capps
MYCRMSIM
View profile →
"Turning the GoHighLevel affiliate ecosystem into compounding revenue"
GHL Go Commander
GHL Go Commander · Affiliate Expert
Russell Robichev
View profile →
"Engineering offers that convert and products that scale"
Offer & Development Expert
Offer & Development Expert
Ron Graziano
GoHighLevel
View profile →
Hover a card for details · tap to view full profile
Apply to Speak+ More to be announced
Proudly sponsored by HighLevel
When one of the fastest-growing software companies in the world supports an event, it says something.
HighLevel continues to be a major part of Kicking SaaS Summit, not simply as a sponsor, but as a partner committed to helping entrepreneurs build better businesses through technology, automation, AI and community.
You'll hear directly from HighLevel leaders, partners and some of the ecosystem's most successful agencies. Whether you've used HighLevel for years or you're just exploring what's possible, you'll leave with practical insights you can apply immediately.
More than keynotes.
The best speakers don't disappear behind a backstage curtain. They answer questions, join conversations over coffee and sit beside attendees during meals. Learning doesn't stop when the presentation ends. It simply changes locations.
Expect conversations like
- ✦How are agencies using AI to cut costs while improving customer experience?
- ✦What automations are creating the biggest competitive advantage today?
- ✦Where is HighLevel headed over the next several years?
- ✦How are founders building teams without sacrificing culture?
- ✦What's actually working in sales, retention and operations right now?
- ✦How do you build a company that creates freedom instead of consuming your life?
Choose your experience
Three ways to experience Costa Rica.
Every ticket includes your plus one. No matter which you choose, you'll spend four unforgettable days surrounded by entrepreneurs who are building what's next. Every attendee receives full access to the education, the networking, the community events and every chef-prepared meal and drink. The difference is simply how you want to experience Costa Rica.
Early bird pricing ends October 1
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General Admission
For founders who already have accommodations or prefer to book their own.
$1,500$2,997
Early bird through Oct 1 · 15 seats left
Complete access to the summit while you choose accommodations that fit your travel style and budget.
- ✔Four days of keynote presentations
- ✔Expert-led workshops
- ✔Live AI demonstrations
- ✔Founder panel discussions
- ✔All meals chef-prepared, plus drinks, included every day
- ✔Welcome networking reception
- ✔Morning and evening yoga, sound frequency sessions and PEMF therapy
- ✔Community events
- ✔Access to sponsors and exhibitors
- ✔Your plus one included, two General Admission tickets
- ✔Lifetime friendships you didn't know you needed
If you already have plans in Tamarindo, or simply enjoy arranging your own travel, this is an incredible way to experience everything the summit has to offer.
Reserve General Admission →Accommodation not included · book your Tamarindo stay separately
3 and 6 month payment plans available
Premium Experience
The easiest way to experience the summit.
$3,497$5,497
Early bird through Oct 1 · 5 left
If you'd rather arrive knowing everything has already been taken care of, this is your ticket. Everything in General Admission, plus:
- ✔Your plus one included, two Premium tickets
- ✔Four nights at a beachfront resort in Tamarindo
- ✔Premium reserved seating
- ✔Curated networking dinners
- ✔Beachfront accommodations steps from the summit
- ✔A seamless experience from arrival to departure
Instead of coordinating hotels and logistics, you simply arrive, check in, meet incredible people and enjoy Costa Rica. Sometimes simplicity is the greatest luxury.
Reserve Premium →Nothing to book separately
3 and 6 month payment plans available
★ Most exclusive · Recommended
Inner Circle VIP
Our most exclusive experience. Limited to only 10 entrepreneurs.
$5,497
10 seats only
This isn't an upgraded ticket. It's an entirely different experience. You'll stay inside a private luxury estate at Hacienda Pinilla with fellow VIP founders, invited speakers and members of the event team.
- ✔Private catamaran experience April 25, the day before the event, with food, drinks and snorkeling
- ✔Luxury accommodations inside Villa Tranquila
- ✔Private chef-prepared meals
- ✔Daily breakfast, lunch and dinner
- ✔Unlimited beverages
- ✔Private mastermind sessions
- ✔Exclusive VIP experiences
- ✔Concierge-level service
- ✔Priority seating
- ✔VIP networking events
- ✔Your plus one included, all inclusive for both of you
This isn't about luxury for luxury's sake. It's about proximity. Some of the most valuable conversations happen when there isn't a stage between you.
Reserve Inner Circle VIP →Only ten founders will experience this
3 and 6 month payment plans available
Why entrepreneurs return.
People rarely return because they need more information. They return because of how they felt. They remember walking into a room where everyone understood the journey, conversations that lasted hours, the encouragement, the breakthroughs, the friendships.
We see familiar faces every year. Not because we ask them to come back. Because they want to.
Your investment isn't four days. It's everything that comes after.
Every entrepreneur has bought software that collected dust, courses they never finished, strategies they never implemented. The right event is different. You don't simply leave with notes. You leave with momentum.
People you can call six months later. Partners you didn't have before. Clients you hadn't met yet. Sometimes the greatest return isn't immediate revenue. It's becoming the kind of entrepreneur who sees bigger opportunities because they're surrounded by bigger thinkers.
Common questions
Everything you're wondering.
Deciding to attend an event, especially one in another country, can bring up a lot of questions. Here are the ones we hear most.
Not at all. Many attendees use HighLevel, but the summit is designed for founders, agency owners, AI builders, consultants, operators, marketers and entrepreneurs who want to build better businesses. If you're passionate about growth, innovation and meaningful relationships, you'll feel at home.
Absolutely. In fact, many attendees travel solo. One of the reasons we intentionally keep the event small is so it's easy to meet people, build relationships and become part of the community from day one. You won't feel like you're attending alone for very long.
No. Education is only one part of the experience. There are networking events, hosted dinners, workshops, beach gatherings, casual conversations, wellness activities and plenty of opportunities to connect with other attendees outside the main stage.
VIP Jungle Suites check in at 1:00 PM at Hacienda Pinilla. Premium General Admission checks in at 2:00 PM at a beachfront resort in Tamarindo. The event itself begins at 4:00 PM at Hacienda Pinilla for all ticket holders, including General Admission.
Liberia International Airport (LIR) is the closest airport to Tamarindo. The drive to the resort is approximately one hour. When immigration asks where you're staying, tell them Tamarindo, Guanacaste — the exact resort is confirmed with your booking.
No. We do not provide airport transportation for any ticket tier. Nearly every guest over the last three years has flown in days early, so pickup times are all over the map and we can't be responsible for coordinating them. Getting a ride is easy: certified local drivers are waiting right outside LIR when you walk out, and you'll also get driver options in the app once you buy your ticket. Rides typically run around $40 to $90 USD.
Absolutely. Many attendees choose to experience Costa Rica with someone important to them. Ticket options vary, so be sure to review the details for the experience you're considering.
Every ticket includes all meals and drinks. Everything is prepared on site by our chef, breakfast, lunch and dinner at Hacienda Pinilla, plus the welcome reception and summit hospitality. VIP guests at Villa Tranquila also receive private chef-prepared meals and unlimited beverages at the estate. Dietary needs are accommodated, just let us know at checkout.
If you want proximity, private mastermind sessions, and four days living alongside speakers and fellow founders inside a luxury estate, yes. Only ten entrepreneurs experience it each year. If you're optimizing for the sessions themselves, Premium is the sweet spot.
It's a private catamaran charter for Inner Circle VIP ticket holders only, the day before the summit begins. We set sail at 8:00 AM from Tamarindo Beach and return by 12:30 PM. Food, drinks and a guided snorkeling stop along the Guanacaste coast are all included, along with gear and crew. It's the easiest way to meet the other VIPs, speakers and the event team before the main event starts, so plan to arrive in Costa Rica no later than April 24 if you want to join.
Kaitlyn Lemus Portillo
Founder · Kicking SaaS Summit
A personal invitation
I know exactly what it feels like to want more.
More clarity. More freedom. More connection. More belief that what you're building matters.
I created this event because I wanted a space where entrepreneurs could breathe, think and grow together. Somewhere beautiful. Somewhere honest. Somewhere real.
Every year, I watch people arrive uncertain and leave inspired. I watch friendships form. I watch confidence return. I watch people remember why they started.
If you've read this far, something inside you is already curious. Maybe you're ready for a change. Maybe you need perspective. Maybe you simply want to be around people who get it.
Whatever the reason, I hope you'll join us in Costa Rica.
The final invitation
Some decisions change your year. Some change your life.
Four days in Costa Rica. One hundred entrepreneurs. Conversations you can't schedule and relationships you can't buy.
You can keep building alone, or you can build beside the people leading what's next. Seats are limited and they go every year.
Still not sure?
Book a Zoom with our team and we'll walk you through which ticket fits you best. No pressure, just a real conversation.
Book a Zoom with our team →April 26-29, 2027 · Tamarindo · Guanacaste · Costa Rica
From $1,500 · 15 leftPrice rises Friday
Reserve →