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Málaga Leadership Offsite — Follow-Up

Action Planning & Owners

Translate priorities into commitments

April 16, 20263 weeks post-offsite
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Where We Are

We're aligned.
Now let's build the how.

Málaga gave us something rare: a team that met for the first time and left with shared clarity on the what and the why. Nine priorities, stress-tested and ranked. Real concerns surfaced honestly.
Today we translate that clarity into action. Owners, deadlines, sequencing — the how that everyone asked for.
This session: recap what we agreed, check alignment with Q2 OKRs, assign owners, set deadlines. One hour.
The 18-Month Window
Oct 2025 Apr 2027
Now
6 of 18 months used
The window is open. Let's use it.
Recap

The 9 Priorities

Ranked by team urgency rating. Two added during the stress test.

1
Accelerate Enterprise Revenue
Urgency: 5.0 / 5 (unanimous)
3
Fix the Product Experience
Urgency: 5.0 / 5 (unanimous)
6
Security Is a Liability
Urgency: 5.0 / 5 (unanimous)
5
Fix the Operational Plumbing
Urgency: 4.7 / 5
7
Platform Stability Is Fragile
Urgency: 4.0 / 5
2
Build the Partner Channel
Urgency: 3.8 / 5
4
Clarify What We Are
Urgency: 3.3 / 5
8
Engineering Velocity Added
Added during stress test
9
Culture & Morale Added
Added during stress test
The tension remains: Revenue priorities (1, 2) need Product (3), Security (6), and Stability (7) solved first. Engineering Velocity (8) underpins everything. Plan confidence was 3.7 / 5 — the team believed in the priorities but wasn't confident we could execute.
Unfinished Business

What we carried out of Málaga

Remaining concerns and parked items — inputs into today's planning.

Remaining Concerns

Joe
How we prioritize and ensure execution — we have a lot to tackle, a small team, and tremendous headwinds from own goals.
Anna
Execution — how can we deliver and when.
Janine
Clear picture on the WHAT & WHY, let's do the work on the HOW.
Charles
Infrastructure migration.
Lizzie
A lot of priorities — progressing as much as we can whilst maintaining team alignment and culture.
Tiff
Bringing AI to all, getting them up to desired level.

Parking Lot (unresolved)

Building a research engine — quantitative, statistically significant, shared internally and externally Joe, Category
Data warehouse — what do we mean and how urgent? Brainstorm requirements Joe, Product Vision
Autonomous agents — who is actually using them? Enterprise, self-serve? Tiff, Agenda
Team change management — departures, messaging, morale, and comfort during disruption Lizzie + Joe, CTO Assessment
CS ownership, scope, and overlap with other departments; rename to Customer Success & Support Janine + Joe
Internal notetaker feeds central documentation Joe, Ways of Working
The Exercise

How we're going to work through this

For each action item, we'll assign an owner, a priority rank, and a target month. Items will re-order by priority as we go.

Priority Ranks

P0
Do immediately
Within 2 weeks.
P1
Do within the next month
Completed within 30 days.
P2
Do this quarter
Deliver by end of June.
P3
Park it for now
Important but not this quarter. Revisit later.

What you're filling in

Owner — who is accountable (one person)
Rank — P0 through P3, drives the order and deadline
Deadline — auto-set from rank (2 weeks / 30 days / end of Q2 / parked)
Notes — context, dependencies, blockers

How we'll use it

We walk through each cluster together
Discuss, debate, assign — items re-sort by rank as we go
After all clusters: updated sequencing view
Then: personal commitments and follow-up cadence
Revenue & Growth
The Salesforce $600k gap and the growth investment question are unresolved. What's the single most important revenue action for the next 30 days?
From Action Owner Rank Deadline Notes
Enterprise Rev --
Enterprise Rev --
Partner Channel --
Enterprise Rev --
Enterprise Rev --
Enterprise Rev --
Enterprise Rev --
Category Rollout
This needs to be a sequenced work stream. Open questions: What do we say publicly in 2026? Timeline for the three commercial gates? Should the company rename?
From Action Owner Rank Deadline Notes
Category --
Category --
Category --
Category --
Category --
Product & Onboarding
Onboarding and HubSpot are the two highest-impact items blocking PLG and enterprise readiness. Onboarding was rated 5/5 urgency by every person. What's the status?
From Action Owner Rank Deadline Notes
Product Exp --
Product Exp --
Product Vision --
Product Exp --
Org Planning --
Ops Plumbing --
Ops Plumbing --
Operational Plumbing & Project Taproot
Project Taproot needs to be a named initiative, not scattered line items. Who drives it? What's the scope and timeline?
From Action Owner Rank Deadline Notes
Ops Plumbing --
Ops Plumbing --
Taproot --
Taproot --
Taproot --
Ops Plumbing --
Closing --
Ops Plumbing --
Foundation & Infrastructure
Security was rated 5/5 urgency. SOC2 is a Q3 enterprise prerequisite. What's the 30-day plan?
From Action Owner Rank Deadline Notes
Stability --
Stability --
Eng Velocity --
Eng Velocity --
Security --
Security --
Eng Velocity --
Eng Velocity --
People & Culture
75% of leadership reported work-related sleep problems. How are we taking care of this team while asking them to execute at pace?
From Action Owner Rank Deadline Notes
Parked --
Parked --
Culture --
Culture --
Closing --
Org Planning --
Closing --
Parked --
What We Just Decided

Action items by priority

Live view of everything ranked in today's session, grouped by owner. P3 (parked) items excluded.

Waiting for inputs

Assign ranks on slides 8–13 and this view will populate automatically.

Does this reflect what we just agreed? Anything missing or mis-assigned?
Add a new action item
Gut Check

Attention vs. Urgency

Bar length = weighted effort (P0 counts 4x, P1 counts 2x, P2 counts 1x). Black marker = urgency score. Gaps between bar and marker reveal under-investment.

Does this match your gut feeling? Where are the biggest gaps between urgency and attention?
Gut Check

Workload by Person

Bubble size = total items assigned. Color segments show priority breakdown. Includes all items, even unranked.

P0
P1
P2
P3
Unranked
Is this distribution sustainable? Does anyone need help, or is anyone missing from the plan?
Alignment Check

Priorities vs. OKRs in Linear

Now that we've ranked action items, let's check: are our OKRs aligned with what we just decided matters most?

Priorities with OKR/Project Coverage
P1: Enterprise Revenue
Book $1M in ICP-qualified ARR (Backlog)
Enterprise Discovery Process (In Progress, Tiff)
P2: Partner Channel
Build prioritised tech integration partner pipeline (Backlog)
Client Journey Asset Mapping (Backlog, Marcos)
P3: Product Experience
Remove integration as primary failure point (In Progress, Venessa)
One-Click Integration (Planned, Venessa)
Scalable activation program (In Progress, Aliya)
Early-warning system for churn (Planned)
P4: Category
Launch category engine (In Progress, Hannah)
Competitive intelligence loop (In Progress, Anna)
P5: Operational Plumbing (partial)
CRM Data Quality (In Progress, Tiff)
Knowledge base up-to-date (Backlog, target Mar — past due)
P7: Platform Stability
Infrastructure modernization (Backlog, target Mar — past due)
Kubernetes migration to DigitalOcean (In Progress, Mark)
Customer impact understanding (Backlog, target Mar — past due)
Priorities with No OKR Coverage
P6: Security
SOC2 project exists but in Backlog with Dec 2026 target. Pentest planned. No OKR for 30-day security basics, questionnaire process, or offboarding.
P8: Engineering Velocity
No OKR. Team composition, AI transformation plan, and delivery strategy have no tracking in Linear.
P9: Culture & Morale
No OKR. Change management, AI adoption enablement, team departures messaging — none tracked.
Other Observations
3 OKRs have March 2026 target dates that are past due and still in Backlog (infrastructure modernization, customer impact, knowledge base).
Several OKRs have no lead assigned and sit in Backlog — created but never activated.
Project Taproot (Notion governance, Slack audit, documentation) has no project or OKR despite appearing in 3+ sessions.
Now that we've ranked action items: which of these gaps need OKRs? Which existing OKRs need owners? What's the threshold for incorporating action items into OKRs vs. tracking them separately?
Accountability

Follow-Up Cadence

The Format
Weekly check-in in the leadership sync

Standing agenda item. Each owner gives a brief update on their P0 and P1 items. Blockers surface here, not in Slack threads.

Open Questions

How do we track this?

How do we track the action items so everyone understands what they signed up for and we all understand progress? What's the system of record?

How does this fit into OKRs?

Are some action items already in our OKRs? Should the rest be incorporated? What's the threshold for adding them vs. keeping them separate?

The next 90 days define the year.

This team — the six of us — this is the team that does it.

Málaga gave us clarity. Today gives us accountability.