Two-Day Leadership Offsite
Wednesday–Thursday, August 5–6, 2026 · following the Q3 board meeting
Naomi OkaforCEO
Maya SundaramCTO
Talia RosenCPO
Danielle ReyesCRO
Genevieve WellsEA
Day 1
Wed, Aug 5
· Financial and operating decisions
8:309:00
Opening and goals for the two days
Agree on the decisions we must leave with, and the norms for getting there.
Owner · Naomi Okafor (CEO)
Discussion9:009:45
ARR and net revenue retention targets
Decide the next-year ARR and NRR targets we will plan against.
Owner · Naomi Okafor (CEO) · prework: draft targets circulated one day prior
Presentation9:4510:00
Morning break · 15 min
10:0010:45
GTM efficiency review
Align on whether CAC payback, magic number, and pipeline coverage support the targets, and flag where they do not.
Owner · Danielle Reyes (CRO) · prework: metric pack
Presentation10:4511:30
Compute economics and gross margin
Agree the gross-margin floor and the inference-cost-as-percent-of-revenue assumption the operating plan will use.
Owner · Maya Sundaram (CTO) · prework: cost and margin model
Discussion12:302:00
Operating plan and headcount workshop
Draft the operating-plan envelope and the headcount lines by function for next year. Builds directly on the morning's targets and margin floor.
Owners · Naomi Okafor, Maya Sundaram, Talia Rosen
Workshop2:002:15
Afternoon break · 15 min
2:153:00
International engineering hiring: go / no-go
Decide whether to hire engineers internationally, and if yes, agree the locations and the headcount range.
Owner · Maya Sundaram (CTO) · prework: entity & cost-of-employment options from Talia
Discussion3:003:15
Day 1 wrap-up
Confirm the decisions logged today and preview Day 2.
Owner · Genevieve Wells (EA) · keeper of the decision log
Discussion6:309:00
Team activity: cooking class and dinner
Build the trust the group needs before Day 2's sensitive sessions. The social evening is deliberately placed before the compensation redesign.
Organized by · Genevieve Wells (EA)
Social
Day 2
Thu, Aug 6
· Strategy, compensation, and decisions locked
8:308:45
Day 2 opening and recap
Confirm the Day 1 decisions carried forward and lock the Day 2 decision list.
Owner · Naomi Okafor (CEO)
Discussion8:459:45
Series D narrative and category positioning
Agree the one-sentence category positioning and the three proof points the Series D story leads with. An energizing reconvene after the team dinner.
Owner · Naomi Okafor (CEO)
Discussion9:4510:00
Morning break · 15 min
10:0012:00
2 hours · fixed · sensitive
Compensation and equity band redesign
Decide the new comp and equity bands, and agree how the sales-comp changes are rolled out to Danielle's team. Placed on Day 2 after momentum is built, and neither first nor last. Includes a 5-minute midpoint stretch that does not count against the 2 hours.
Owner · Talia Rosen (CPO) · Danielle's concern is on the agenda by name · prework: draft band structure two days prior
Workshop12:001:00
Lunch · 60 min · a natural cool-down after the comp session
1:001:45
AI-usage and data-governance policy
Agree the internal policy for AI-tool usage and data handling, and name its owner.
Owner · Maya Sundaram (CTO) · owner to confirm (see open questions)
Discussion1:452:00
Afternoon break · 15 min
2:003:00
Closing: decisions, owners, dates
Confirm every decision from both days with a named owner, a date, and what gets communicated to the company and by whom.
Owners · Naomi Okafor (CEO) and Genevieve Wells (EA)
Workshop
Open questions for Naomi and Maya
To confirm before the agenda is circulated.
- Final attendee list. Beyond the five leaders, do Finance, RevOps, or IT join specific sessions (for example the operating plan or the AI-governance policy), or is the offsite leadership-only?
- Sequencing of AI-governance vs comp. Both touch how people feel about how they are treated. The draft places AI-governance after the comp session; confirm that order, or move it ahead if you would rather settle policy before pay.
- Danielle's participation. Does the CRO attend the full two days, or primarily join for the comp and equity session where her concern is centered?
- Team activity. The cooking class and dinner were noted tentatively. Confirm the activity, venue, and the 6:30 start.
- Day balance. Day 1 finishes mid-afternoon and Day 2 ends at 3:00. If you prefer more even days, we can pull Series D into Day 1's late afternoon; it sits on Day 2 morning here as an energizing reconvene.
- AI-governance ownership. The brain dump did not name an owner; it is assigned to Maya by subject fit. Confirm, or reassign.