Day 1 — 9:00

Opening & Context Setting

Málaga Leadership Offsite

March 24–26, 2026

Icebreaker

Spectrum Exercise

Select a person, then click on the bar to place their dot.

1 / 9

Select a person, then tap the line to place their position

Analysis

Spectrum Summary

Where we agree and where we diverge

Team divergence on each question, sorted by spread.

Our Values

How We Work

Ownership

"Own the outcome, not just the task."

Take responsibility for results Step up and own projects, both successes and setbacks. Proactively seek solutions.
Act with a long-term mindset Treat every deliverable as if it were yours forever. Consider maintenance, scalability, and future impact.
Champion quality & transparency Own the data, documentation, and communication so teammates can trust the work and build on it.

Autonomy

"Understand the strategy, then make the call."

Empower decision making Make sure you understand the strategy and make the right decisions without waiting for permission.
Experiment! Iterate quickly. Don't be afraid to fail. Learn from mistakes and improve over time.
Foster self-service resources Build the tools, contribute to documentation, track the metrics that matter.

Shared Outcomes

"Your goals and our goals are the same goals."

Align on collective goals Know how your work connects to company goals. Ask questions if you don't understand.
Collaborate across teams Break silos through communication, shared metrics, and celebrating joint successes.
Remember we are on a team Everyone plays an important role. Step up to help others. Think about the big picture every day.

Context

Where We Came From — FY25

FY25 Revenue

~$11M

+9% YoY

Gross Margin

88.55%

+12% from FY24

EBITDA Margin

62.18%

+2% YoY

MRR Growth

+43%

$558k → $800k

ARPC

~$400

Up 38%

SLG Revenue

$1.7M

+6% vs budget

Milestones

Pricing project completed — eliminated grandfathering, customers no longer below cost
Built a product function from scratch — everything was engineering-led/casual before Anna joined
Team transformation: 10 departures, 9 hires, 3 short-tenure exits in FY25 alone
Notable enterprise wins: Disney, Figma, FIFA, Zara Preowned
Nexus integration copilot launched

Discussion

Before we look at where we are now — what's the thing from last year you're most proud of?

People

Team Transformation

The Numbers

16

departures

23

hires

across 15 months

More than half the company is new.

Engineering — The Hard Part

Engineering was rebuilt twice
Artem departed → Carlos hired July '25 → resigned Dec '25 → Charles hired March '26
Team went from 10 → restructuring to 7 + CTO
Carlos resigned Dec '25. Two hires terminated during probation in the search for the right fit.
We learned: fewer, better, AI-first. Charles is the leader we needed.

The Target State

CEO — Joe

Director of Growth — Tiff

Marketing, Sales, Partnerships

Director of Product — Anna

Roadmap, UX, Research

CTO — Charles

Engineering, Architecture, AI

Director of Support & CS — Janine

Onboarding, Retention, NPS

Head of Operations — Lizzie

Process, Systems, Execution

The leadership team is complete. The structure is complete.

Context

Where We Are — Current

ARR

$9.5M

+32% YoY

Rule of 40

87.9%

+18pp YoY

Revenue YTD

$2.0M

−1.6% vs budget

EBITDA YTD

$1.1M

+31% vs budget

The Scissors — Revenue vs. EBITDA

More profitable, growing slower

Revenue forecast

−2.79%

$14.2M forecast $14.6M budget

EBITDA forecast

+9.11%

$6.5M budget $7.1M forecast

The 2026 mandate: invest margin for growth. Trade lower EBITDA for higher revenue.

Reality: we're doing the opposite. Higher EBITDA, lower revenue.

Good for the board short-term. Not sustainable long-term for the company.

But the leading indicators are strong

Integration activity — monthly

Enterprise pipeline $646k → $955k +48%

NDR

~125%

Gate: >110%

Passing

GDR

~80%

Gate: >85%

Below

Enterprise ARR

$955k

Gate: $1M

At Risk

Partner ARR

$230k

Gate: $500k

Behind

NPS

—

Gate: >35

Not Measured

FAR

—

Gate: >30%

Not Measured

We set six gates. Passing one. Close on two. Behind on two. Can't measure two.

Discussion

What's the number on this screen that concerns you most?

Context

What's At Stake

$600k Salesforce Gap

Our largest partner is not renewing. The revenue hole is real.

Revenue Shortfall Across All Channels

Partnerships, enterprise, AND self-serve are all behind plan.

18-Month Category Window

The time to own "Machine Visibility" is now. Cloudflare and Botify are moving.

The Opportunity

EBITDA headroom: +$500k+ above plan
Integration activity at all-time highs
Enterprise pipeline +48% and growing
The strongest leadership team we've ever assembled is in this room

The Big Question

We have EBITDA headroom. Do we invest it in growth, protect the margin, or something else?

We'll come back to this on Day 2.

Agenda

The Two Days

Day 1

Where are we going?

9:00 — Opening & Context Setting
10:30 — Personal Intros & Working Styles
12:00 — Category Creation
14:00 — Product Vision
15:30 — CTO Technical Assessment
17:00 — Synthesis: Where are the tensions?

Day 2

How do we work together to get there?

9:00 — Cross-functional Ways of Working
10:30 — Organizational & Resource Planning
12:00 — Priority Alignment & Stress Test
14:00 — Action Planning with Named Owners
15:30 — Feedback & Closing

What has to be true by the end of 2026 for this to have been a successful year?

Hold this question through today. We'll come back to it.