Created: February 16, 2026
Prepared for: Kristin (Partner Relations)
Timeline: February 2026 β July 2026+
Status: Ready for 1-on-1 rollout
This plan orchestrates three concurrent transitions:
Key principle: Automation and delegation enable growth, not add burden. Carmee gains design work because pathways become automated, not because she's suddenly doing both. Charlie gains strategic time because Minnie handles admin, not because she's scrambling.
Success = 3 things:
Automate what can be automated, document what must be handed off, and get Carmee ready to learn design.
Lead: Paula + Kristin in 1-on-1
Timeline: Week of Feb 17
Paula documents:
Output: Transition checklist (shared doc)
Notes for Kristin's 1-on-1: "We need to know exactly what lives in Paula's head right now. No surprises during leave."
Lead: Quan + Charlie
Timeline: Week of Feb 17 β Mar 8
Minnie takes over:
Charlie's freed time: Target 8-10 hours/week by March 15
Notes for Kristin's 1-on-1: "This is about Charlie actually seeing the time freed up. Test it. Have her report back on what she can do with the extra 8 hours."
Lead: Carmee + Quan (AI arch)
Timeline: Week of Feb 17 β Mar 15
Audit current pathways for automation:
Target: Reduce Carmee's pathway work by 20-30% by March 15
Notes for Kristin's 1-on-1: "Carmee needs to see her freed time before she takes on design. Otherwise she'll just fill the gap with more pathways."
Lead: Quan + external design mentor (TBD)
Timeline: Week of Feb 17 onwards (ongoing)
Carmee needs:
Jedi Council (Tue/Thu design sprints):
Notes for Kristin's 1-on-1: "Design is hard. Carmee is smart but this is new. She needs a mentor, not just training videos. Budget for external design support (freelancer or agency retainer for complex projects)."
Lead: Tin + Quan
Timeline: Week of Feb 17 β Mar 8
Determine what Valencia will handle:
Notes for Kristin's 1-on-1: "This frees Tin from repetitive fulfillment work. Check in with Tin on what this does for his capacity and morale."
Lead: Paula + Kristin
Timeline: Two weeks before leave (~mid-March)
Paula trains/hands off to:
Two-week overlap post-announcement:
Notes for Kristin's 1-on-1: "Paula needs a clean handoff, not a 'please monitor from home' vibe. Make the boundary clear."
Lead: Charlie + Quan
Timeline: Mid-March onwards
Charlie now has capacity for:
What Charlie stops doing:
Success metric: Charlie reports at least 2 brand strategy initiatives launched by end of April
Notes for Kristin's 1-on-1: "Check in on whether Charlie actually shifted mentally. Sometimes people keep the old task 'just in case.' She needs permission to stop."
Lead: Carmee + Quan
Timeline: Mar 16 onwards
By March 31:
Portfolio goals by April 15:
Notes for Kristin's 1-on-1: "Design takes time. We're looking for progress, not perfection. Ask Carmee what's working and what's scary."
Lead: Coverage person (TBD) + Kristin
Timeline: April 1
Whoever's covering:
Backup plan: If coverage person falls behind, escalate to Quan.
Assumption: Paula on full maternity leave starting April 11 (~12 weeks)
Social media continuity: Coverage person keeps it live, minimal changes
Community building: Hold position, don't grow aggressively (Paula can catch up)
Social-first projects: Defer until Paula returns (avoid major pivots)
Carmee: Continues design work + pathways (automation sustaining her)
Charlie: Continues brand strategy (no regression to admin)
Minnie: Keeps running automation (Quan watches for gaps)
Lead: Paula + Kristin + Quan
Timeline: Start conversation mid-June
Paula can choose from:
Option A: Full Return (Jul 1)
Option B: Phased Return (Jul 1-31)
Option C: Part-Time/Contract (Jul 1+)
Option D: Delayed Return (Aug 1)
Key: Decide by mid-June, communicate to team by end of June
Notes for Kristin's 1-on-1: "This is a conversation with Paula, not a decision made for her. Start early. What does she want? What does the team need?"
Purpose: Unblock Carmee, elevate design quality, catch problems early
Attendees:
Frequency: Tuesday & Thursday, 60 min each
Agenda:
Outcomes:
Success metric: No design project stuck for >3 days waiting for feedback
Purpose: Keep AI automation working, catch new automation opportunities
Weekly check-in: Quan + Minnie (Wed AM, 15 min)
Monthly review: Quan + Charlie + Minnie (last Wed, 30 min)
Purpose: Smooth handoff of RMA/shipping, maintain quality
Kickoff: Week of Mar 1
Weekly check-in: Tin + Valencia manager (Mon AM, 15 min)
Scenario: Pathways automation doesn't deliver, Carmee drowns with both jobs
Prevention:
If it happens:
Scenario: Carmee ships designs that need rework, projects slip
Prevention:
If it happens:
Scenario: Paula doesn't return, or returns only part-time. Coverage person wasn't trained as permanent.
Prevention:
If it happens:
Scenario: Urgent admin tasks come up, Charlie "just handles it" instead of saying no
Prevention:
If it happens:
Solution: Protect Charlie's calendar (Quan blocks Tuesday/Thursday for strategy, no meetings)
Scenario: Valencia takes work but gaps/delays require Tin to backfill
Prevention:
If it happens:
Track these weekly (Kristin reports to Quan):
Admin hours freed: Target 8-10 hrs/week by Mar 15
Brand projects launched: 2+ strategic initiatives by end of April
Time spent on brand work: 20+ hrs/week by April 1
Pathway time reduced: 30% reduction by March 15
Design projects completed: 3-5 designs by April 15
Design mentor engagement: Weekly 1-on-1s happening
Confidence growth: Carmee self-rates at 4/5 or higher by April
Handoff completeness: All docs ready by Mar 15
Social media continuity: No drops in posting or community engagement
Return decision made: Paula communicated preference by June 15
Coverage person readiness: Can run independently by June 15
Minnie automation stability: No admin tasks slipping through
Design delivery pace: No project delays attributed to design
Team morale: No burnout signals
Valencia partnership: RMA/shipping is stable
Use this when holding 1-on-1s to roll out the plan:
Feb 16 - Mar 15 PHASE 1: FOUNDATION
ββ Minnie automation sprint (Charlie's admin)
ββ Pathway automation foundation (free up Carmee)
ββ Paula's responsibility audit (handoff docs)
ββ Carmee design onboarding begins
ββ Valencia fulfillment prep
ββ Jedi Council starts (Tue/Thu)
Mar 16 - Apr 10 PHASE 2: SOFT LAUNCH
ββ Paula transitions to leave (final 2 weeks, then PTO)
ββ Charlie brand strategy launches
ββ Carmee design projects in progress
ββ Social media coverage goes live (Apr 1)
ββ Valencia testing begins
Apr 11 - Jun 30 PHASE 3: PAULA'S LEAVE
ββ Coverage person runs social media
ββ Carmee + pathways maintain baseline
ββ Charlie focuses on brand strategy
ββ Minnie keeps automation running
ββ Mid-June: Paula return conversation starts
ββ End of June: Return decision finalized
Jul 1 - Aug 31 PHASE 4: PAULA'S RETURN
ββ Paula returns (full, phased, part-time, or delayed)
ββ New coverage/social model implemented
Sep 2026+ STABLE STATE
ββ New team roles operating normally
ββ Carmee design team growing
ββ Charlie brand strategy delivering
ββ Automation supporting everything
For Quan (CEO):
For Kristin (Partner Relations):
Metrics Tracking Template (Weekly Report to Quan):
Week of [DATE]:
CHARLIE
ββ Admin hours freed: [X] hours
ββ Brand projects: [In progress / Completed]
ββ Morale: [Notes from 1-on-1]
CARMEE
ββ Pathway hours: [X] hrs/week (target: -30% by Mar 15)
ββ Design projects: [In progress / Completed]
ββ Mentor engagement: [Happened? Notes]
ββ Morale: [Notes from 1-on-1]
PAULA
ββ Handoff status: [% complete]
ββ Coverage person readiness: [% ready]
ββ Return decision: [Pending]
SYSTEM HEALTH
ββ Minnie status: [Working / Issues?]
ββ Design delivery: [On track?]
ββ Team morale: [Overall pulse]
ββ Valencia status: [On schedule?]
RISKS / ESCALATIONS:
[Any red flags?]
This plan is ready. Kristin has everything she needs for 1-on-1s. Quan reviews, approves, and we roll it out week of Feb 24.