The Week Wonsulting Took Over New York

Culture

By
Hassan Bayo Adesoka

We’ve had offsites before.
Different cities. Different seasons. Different goals.

But this one felt different even before we stepped off the plane. Maybe it was the momentum we’d built this year. Maybe it was the feeling that Wonsulting was entering a new chapter. Or the mix of people, energy, and timing just made everything crackle.

We didn't know. But we were about to find out in the most Wonsulting way possible.

Spoiler: It involved cold plunges, color personalities, rock climbing, revenue charts that told hard truths, 10x dreams, legendary pizza spots in NYC, and the kind of conversations that change the trajectory of a company.

Let's rewind.

Why We Met (And Why It Matters)

We've always been a remote team. Our founders, Jon and Jerry, have always been together. But the rest of the team spans cities, countries, and time zones, connected by Slack messages and Google Meets squares.

Naturally, it works. We've helped thousands of job seekers land their dream roles without ever being in the same room.

But there's something about meeting face-to-face that video calls can't replicate. The energy. The breakthroughs. The kind of conversations that happen over cold plunges and pizza at 10 PM.

So we did something we'd only done twice before: We brought the leadership team to New York City for three days of connection, strategy, and let's be honest, a little chaos.

Day 1: The Warm-Up (aka The "Are We All This Tall in Real Life?" Day)

Everyone flew in. Everyone hugged. We were excited to see each other again in person, and tired from the long flights. 

Escape Room: Where Strategy Meets Chaos

Our first night was at an escape room, where we solved some fun puzzles and got our creative juices flowing. Nothing like being locked in a room together to accelerate team bonding.

Brooklyn Exploration

The next day, we started by exploring Williamsburg and Greenpoint. The kind of Brooklyn neighborhoods that somehow feel gritty and bougie at the same time, places where a craft coffee shop sits next to a bodega that hasn't changed since 1987.

Rock Climbing → Lunch → Bathhouse

Then we hit Vital for rock climbing. Nothing builds trust like watching the coworker who's usually calm and composed on Slack suddenly cling to a wall like a terrified house cat in athletic gear.

After lunch at Hole In The Wall (because where else?), we headed to Bathhouse Williamsburg. Cold plunge. Sauna. A pool with a view that tricks you into forgetting you're not on vacation.

This is where the Zoom barrier started breaking. You can't be formal when you're sweating in a sauna together.

The Legendary Pizza Crawl

By evening, we were ready for the main event: hitting five of New York's top pizza spots in one night.

Was it excessive? Absolutely. Was it worth it? Ask anyone, especially Alif, our Sales lead, and Jerry, our Co-founder. (But don't tell them Marketing called them the life of the party)

The first phase of the meetup accomplished exactly what it needed to: it turned coworkers into teammates. It built trust and set a relaxed, open foundation for the deeper work ahead.

Day 2 - Morning: Looking in the Mirror

If Day 1 was about connection, Day 2 was about confronting reality, and reimagining what's possible.

Leadership Weekly: Setting the Stage

We kicked off with our regular leadership sync, but this time in person. The energy was different. Seeing faces instead of squares changes everything.

2025 Reflection: The Revenue Reality Check

Then came the moment that would set the tone for everything else.

Jonathan pulled up a chart showing our total revenue by month for 2025. And there it was, plain as day: a dip that stretched from January through July.

The room got quiet.

The Three Insights That Changed Our Trajectory:

1. The dip showed where our collective knowledge had reached its ceiling. We'd been optimizing the same strategies, running the same playbooks. We needed fresh eyes and new approaches.

2. This period wasn't wasted, it helped us identify where the biggest opportunity for growth was: systems, 10x thinking, and pilots. We learned what not to do. And more importantly, we learned we needed to think bigger.

3. It reinforced our team's #1 ability: There is no problem we cannot solve. Because look at what happened next: August and September showed a sharp rebound. 

What changed?

  • We stripped away assumptions and started making decisions based on real signals instead of guesswork.
  • We moved to a more agile approach that let us test, learn, and adjust faster.
  • We brought in external expertise to unlock solutions we hadn't considered.
  • The right combination of mindset, process, and people changed outcomes almost overnight.

But Jon didn't let us celebrate yet. He pulled up another slide.

The Hypothesis Tree: What We Got Wrong

Ken had built a detailed hypothesis tree back in January, breaking down every element that drives conversions:

  • Content Strategy (selection, structure, timing)
  • Psychological Elements (persuasion frameworks, trust building)
  • Visual Design (layout, components)
  • CTA & Action Elements
  • Offer Elements (value configuration, offer framing)

Ken's hypothesis tree was solid. The problem? We focused on the wrong branches.

The Insight: "We had the right hypothesis tree, but we focused on the wrong branches. We assumed the offer was strong enough and left it unchanged."

We'd been optimizing copy, tweaking CTAs, testing visual layouts, all while ignoring the foundation: our actual offer.

The Hard Truth: "Our underlying assumptions kept us from questioning the status quo. We optimized for incremental gains instead of exploring bold changes."

The Real Learning: "Mindset matters as much as strategy. Without challenging defaults, even a solid framework leads to limited progress."

This wasn't just a marketing lesson. It was a company-wide wake-up call.

Team Goal Alignment: Getting Everyone on the Same Page

With the year's narrative laid out, we moved into goal alignment. Each team lead shared their priorities for Q1. But more importantly, we talked about how those goals interconnected. Because we learned from the revenue dip that siloed excellence doesn't scale. Systems that work together do.

Lunch Break

We needed it. That was a lot to digest, literally and figuratively.

Day 2 - Afternoon: The Transformation Sessions

Culture & Ways of Working: Courage vs. Comfort

After lunch, Cadogan, our head of revenue, stood up and wrote two words on the board:

COURAGE COMFORT

He asked us to write down the first four words that came to mind for each. Ken saw "courage" and immediately thought: brave, determined, confident. Bold moves forward. Another team member looked at the same word and wrote: nervous, unstable, chaos.

Same word. Completely different interpretations. Cadogan let that hang for a moment. Then he made the point that would echo through the rest of the offsite:

"Words don't carry meaning. People do."

If something as simple as "courage" means ten different things to ten different people, what does that mean for how we write copy, how we coach job seekers, how we talk to teammates, and how we communicate our vision as a company?

The Implication: If we want our messaging (whether internal or external) to actually land, we need to speak in ways that multiple "inner dictionaries" can understand. We need to meet people where they are, not where we think they should be. This was supposed to be a communication exercise. It turned into a self-discovery moment.

(Someone may or may not have gotten emotional. But what happens in New York stays in New York.)

Zone of Genius: Finding What Makes You Unstoppable

Then came an exercise that would help us understand not just how we communicate, but where we thrive. The framework breaks down into four zones:

  1. Zone of Incompetence: Activities other people do better than you and that drain your energy.
  2. Zone of Competence: Things you do fine, but so can others. They might bring you joy, but they're not unique to you.
  3. Zone of Excellence: Activities you're excellent at, better than most, in fact but don't love doing. When you're honest with yourself, these drain your energy.
  4. Zone of Genius: Activities you are uniquely good at in the world, and that you love to do, so much so that time and space likely disappear when you do them. These activities charge up your metaphorical batteries.

Everyone took 15 minutes to map their own zones.

Jerry's Example (Our Co-founder):

Zone of Genius:

  • Structured Problem Solving.
  • Data Analysis.
  • Poking holes & breaking systems of logic.
  • Bringing energy.
  • Strategy.

Zone of Excellence:

  • Social media ideation & scripting.
  • Operations.
  • Copy.
  • Sales.
  • Managing the details of projects.

Zone of Competence:

  • Technical Concepts
  • Delegating
  • Details of a Functional Area (e.g., email marketing, paid ads)

Zone of Incompetence:

  • Design.
  • Manual work (e.g., sending emails one by one)
  • Detailed QA.

The revelation? Jerry's been spending too much time in his Zone of Excellence, doing things he's great at but that drain him, instead of doubling down on his Zone of Genius.

And he wasn't the only one.

When we shared our zones with each other, patterns emerged:

  • People were doing work that wasn't energizing them.
  • Certain Zones of Genius were being underutilized.
  • We had opportunities to restructure responsibilities so people could thrive.

This wasn't just a feel-good exercise. It was strategic talent optimization in real time.

Communication Styles Workshop (Led by Alif)

Alif kicked things off by showing us a video breaking communication styles into four core drivers:

🟥 Power & Results: Direct, decisive, outcome-focused. 

🟦 Logic & Structure: Analytical, organized, detail-oriented. 

🟩 Peace & Stability: Calm, supportive, harmony-seeking. 

🟨 Fun & Connection: Energetic, spontaneous, relationship-driven.

The first thing that followed the presentation was chaos. People guessed their colors. They guessed each other's colors. And it was refreshing to hear how your communication sounds to other people.

Daniel, our product lead, is still surprised he's absolutely NOT the color he thought he was. It was hilarious, revealing, and wildly useful. Because once you understand how someone communicates, you figure out how to collaborate with them.

Peter Luger: Where Ideas Became Commitments

We wrapped the day over steak at Peter Luger. And between bites of some of the best meat you'll ever taste, the conversation shifted.

It wasn't "what if" anymore. It was "what's next."

Day 3: From Vision to Action

If Day 1 was connection and Day 2 was discovery, Day 3 was all about execution.

The 10x Hypothesis Workshop (Led by Daniel, CMO at Cluely)

We were joined virtually by Daniel, CMO at Cluely, a startup that raised $15M from a16z. He brought youthful exuberance and an unforgiving creative work ethic.

His message was simple but brain-bending:

"Stop thinking incrementally. Start thinking 10x."

He asked each of us to identify our "golden metric"—the one number in your role that, if it skyrocketed, would literally change how people think of you.

For Ken, it was career consultation calls booked. (So, if you're enjoying this blog post, do Ken a favor and book a free call so our career consultants can tell you what you really need to do on your job search. Of course, the call comes with ZERO obligations.)

For other members of the team, it was product adoption, revenue, content reach, etc. Then came the challenge:

"What would 10x look like?"

Not 10% better. Not twice as good. Ten times.

If we punch 10x of our regular effort into what we do, what would the result look like?

Daniel's philosophy: Once you identify your golden goal, imagining what 10x effort or 10x creativity looks like massively increases your odds of achieving it. It forces you to think beyond incremental improvements so you can act faster and swing boldly.

The room got quiet. You could almost feel people's minds rewiring.

Strategic Exploration: Building the Experimentation Muscle

The conversation expanded into hypothesis-driven thinking:

  • How do we test ideas faster?
  • How do we experiment without needing everything to be perfect first?

We ran through rapid-fire exercises:

  • Comfort vs. Courage Exercise #1: Where are we playing it safe?
  • Comfort vs. Courage Exercise #2: What bold move scares us most, and why does that mean we should probably do it?
  • 10x Opportunities Exercise: For each golden metric, what's the craziest idea that might actually work?
  • Customer Journey Exercise: Where in the user experience could we create 10x more value?

The energy felt like creativity with a stopwatch. And it kept sparking until it was time for lunch.

Lunch: Refueling

We needed the break. Our brains were full.

Storyboarding: "What If This Works?"

After lunch, we moved into storyboarding, a session Jon led to help us visualize what success actually looks like.

For each of our top 10x ideas, we asked:

  • What does the customer experience if this works?
  • What does the team experience if this works?
  • What does the business look like if this works?

This wasn't just daydreaming. It was pre-mortem planning in reverse. Instead of asking "why might this fail?" we asked "what does winning look like?" And then we worked backward to figure out what needed to be true.

Example: If we 10x career consultation calls booked, what happens?

  • Ken's calendar is full.
  • We need more consultants.
  • We build scalable systems so quality doesn't drop.
  • Revenue grows, but so does customer satisfaction.
  • Our marketing message clearly communicates the value.

Suddenly, "10x calls booked" wasn't just a number. It was a roadmap.

Prioritization and Action Planning (Led by Jon)

Our CEO, Jonathan Javier, brought the 10x conversation full circle.

We revisited our golden metrics. We talked about turning mindset shifts into repeatable systems. We made commitments for Q1 and beyond.

The Framework:

  1. Celebrate: You actually did the thing. (Acknowledge the wins.)
  2. Study: What's the 20% that drove the 80%? (Identify the leverage points.)
  3. Scale: What's the new baseline we just created, and what would 10x of that look like? (Keep raising the bar.)

Example: The 2-Month Job Guarantee

Our original offer: "If you don't land a job in 4 months, we'll give you a refund. 90% offer rate."

What happened when we 10x'd it:

  • New offer: "If you don't land a job in 2 months, we'll give you a refund. 100% offer rate."
  • Results:
    • 3x increase in conversions
    • 5% reduction in refund requests
    • Monthly services revenue grew from $30K → $150K
    • Lowered hesitation and increased trust

This wasn't just a tactic. It was proof that bold moves work. But Jon didn't stop there. He asked: "Now what does 10x of that look like?"

And the cycle began again.

Wrap-Up at Saigon's Bread Café

By the time we gathered at Saigon's Bread Café for our final meal, the energy had shifted. We had a quiet wind-down, Vietnamese iced coffee, and cackled at inside jokes that formed over only 48 hours.

And then we said goodbye, at least until the next offsite.

So… Was This Offsite a Success?

Yes. And the reason is simple. Remote work is powerful. But real human connection is rocket fuel. We're going into Q1 2026 with:

  1. Clearer messaging that speaks to job seekers' real fears and desires
  2. Stronger internal communication because we truly understand each other's styles
  3. An energized approach to growth fueled by 10x thinking
  4. Renewed focus on our mission: helping job seekers 10x their results.

And because after this week, one thing became obvious:

We’re just getting started.

Wonsulting helps job seekers land their dream roles through AI-powered tools like ResumAI, InterviewAI, NetworkAI, and Job Search Plan.

Want to 10x your job search? Start here.

Hassan Bayo Adesoka
Junior Copywriter

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