Draft OKRs

Onboarding squad OKRs, next quarter

Objective 1: New teams get their teammates in during week 1, and stay (supports the company goal: make Fieldnote the place new teams get started)

• KR1: Raise the share of new teams with 3+ people in week 1 from 29% to 45%.
• KR2: Cut the median time from sign-up to the first note someone else opens from 3 days to 1 day.
• KR3: Raise the share of new teams active in week 4 from 34% to 40% (shared with the company KR).

Planned bets, not KRs: onboarding checklist, invite flow redesign, 5 templates, onboarding emails. We'll drop or swap any of them if they aren't moving KR1 and KR2.

Objective 2: Keep the product dependable while we change onboarding

• KR1: Zero open P1 bugs at quarter end, and no P1 open longer than 5 days at any point.

Backlog, not this quarter: dark mode, AI summaries, NPS target, help articles.

---

Note to the squad

Thanks for the draft. Here's what I changed and why.

1. Outcomes, not deliverables. Most of the draft listed things we'd ship. We could ship all of it and leave week-4 activity flat. The checklist, invite redesign, templates and emails are now the bets we make to hit the KRs.

2. One clear line to the company goal. Teams where 3+ people join in week 1 are still active in week 4 58% of the time, versus 21% for everyone else, and only 29% of teams reach 3+ today. So KR1 is about getting more teams to that point. Reaching 40% overall probably needs about 45% of teams there, assuming the relationship holds. KR2 measures how quickly a new team sees value from a teammate.

3. Cut and moved. Dark mode, AI summaries and the NPS target have no clear link to the company goal, and NPS isn't something onboarding alone can move. They go to the backlog, not the bin. User interviews and help articles are useful, but as activities inside Objective 1, not KRs. "Fix 50 bugs" rewarded volume over impact, so it became a P1 guardrail.

4. Two caveats to settle before Friday. - The data implies a week-4 rate of about 32% (0.29×58% + 0.71×21%), not the 34% in the company KR. Likely a definition or timing difference, but I'll confirm which baseline we're using. - The 58% vs 21% gap is correlation. Teams that invite people quickly may already be more committed, so the real lift from nudging invites will probably be smaller. That's why KR3 sits next to KR1, so we'll see whether the outcome really moves.

5. The bonus link. Since scores now affect everyone's multiplier, the safe play is to pick easy, output-style KRs. I've deliberately not done that. KR1 and KR2 are stretch targets, and I'd rather be upfront about it than quietly sandbag. Before Friday I'll ask leadership and HR how scores convert to multipliers, and I'll push for 0.7 on stretch KRs to count as a good result. I'll share the answer as soon as I have it. If you think a target is unrealistic, tell me before Friday so we can adjust it openly.

Please reply with objections or number challenges by Thursday noon.

Q3 Onboarding Squad OKRs (Revised)

Objective: Get new teams collaborating in Fieldnote during their first week.

• KR1: Increase the share of new teams with 3+ members in their first week from 29% to 45%.
• KR2: Reduce the median time from sign-up to a teammate opening a shared note from 3 days to under 24 hours.
• KR3: Increase Week 4 retention for new sign-up cohorts from 34% to 40%.

(Note: Previously listed features like the invite flow redesign, templates, and onboarding emails will now live on our roadmap as the bets we’ll place to hit these numbers).

*

Note to the Squad: What I changed and why

Hey team, thanks for pulling the draft together. Before we send this to leadership on Friday, I’ve made some big cuts and reframed our goals. Because HR is tying our bonus multipliers directly to our OKR score this year, it’s critical that we set ourselves up to win with goals we actually control and can realistically hit.

Here is the thinking behind the changes:

1. One focused Objective tied to company math Leadership’s only goal this quarter is moving Week 4 retention from 34% to 40%. Look at our data: teams with 3+ members in week one retain at 58%, vs. 21% for everyone else. Right now, only 29% of teams hit that 3-member mark. By mathematical average, if we just move the needle on that 3-member metric from 29% to ~45%, we will single-handedly hit the company’s 40% retention target. Furthermore, since Fieldnote charges at 6+ members, getting teams to 3+ in week one is the best thing we can do for the business.

2. Moving from outputs to outcomes Our draft KRs (checklists, templates, invite flow, emails) were a task list. If we ship all four and retention stays at 34%, leadership won’t view the quarter as a success. By making the KRs about behavior (inviting teammates and sharing a first note quickly), we give ourselves the freedom to experiment. We’ll still build the invite redesign and templates, but if they work early, we don't have to build the rest. If they don’t work, we can pivot without failing our OKRs.

3. Protecting our bandwidth (and our bonuses) We are five engineers and one designer. The draft had us building dark mode, AI summaries, and four onboarding features, plus fixing 50 bugs. That’s way too much for one quarter. * Cut "Delight Users" (Obj 3): Dark mode and AI summaries are huge scope creeps for an onboarding team. Also, NPS is a lagging, company-wide metric—we shouldn’t tie our bonuses to a number that core product bugs or pricing changes can tank. User interviews and help articles are great, just as part of our weekly process. * Cut "Improve Quality" (Obj 2): Fixing 50 bugs incentivizes us to hunt for 50 tiny typos, while "zero P1s" is a baseline engineering standard, not a quarterly goal. We will keep squashing bugs in our normal sprint triage, especially anything breaking the sign-up or invite flows, without making it an OKR.

Let’s chat in standup tomorrow to make sure everyone feels good about these numbers before I send them up on Friday!

Proposed onboarding OKRs — next quarter

Objective: Help new teams experience shared value quickly and keep collaborating.

The targets for KRs 2 and 3 are proposed, pending a feasibility review before leadership approval. They are not forecasts of retention impact.

Measurement and quality guardrails

• Freeze cohort eligibility, “active,” membership, and shared-note definitions before the quarter starts. Use consistent definitions for baselines and results.
• Score week-4 retention only on cohorts that have reached week 4; report immature cohorts separately.
• Reconcile the data before approval: the supplied segment figures imply approximately 32% overall retention, rather than 34%. Confirm whether they use different cohorts or definitions.
• Track onboarding reliability alongside these KRs. Critical onboarding defects are release blockers, not a bug-count target.
• Improve collaboration through genuine value—not forced invitations or changes that artificially inflate membership.

Candidate initiatives — not scored key results

Prioritize the checklist, invite-flow improvements, a small set of useful templates, and lifecycle emails according to their expected contribution to these outcomes. Use interviews and funnel analysis to choose and refine experiments.

Defer dark mode and AI summaries unless evidence shows they address a major onboarding barrier. Publish help content where research identifies a specific need.

Note to the squad

I replaced three broad objectives and a shipping checklist with one focused objective and measurable user outcomes. Launches, interviews, articles, and bug fixes are ways to make progress; completing them does not prove that onboarding improved.

Early team participation is our strongest available signal: teams with three or more people joining in week 1 have much higher week-4 retention. That is correlation, not proof of causation, so we’ll test whether our changes improve retention rather than assume invitations alone will do it.

I also narrowed the scope for our five-engineer, one-designer squad. NPS is too broad to diagnose this onboarding problem, while dark mode and AI summaries would compete with the core work.

Because OKR scores now affect bonuses, I want targets, scoring rules, guardrails, and shared ownership agreed before the quarter—not adjusted afterward. We should review the bonus linkage with leadership and HR so it does not reward metric manipulation or discourage honest experiments.