The Playbook on OKRs and KPIs for Startups

General FAQs

When do I introduce OKRs and KPIs?

When your team is large enough to require multiple key stakeholders collaborating to launch cross-team initiatives, you probably need OKRs and KPIs.

When you don’t have enough time to have eyes everywhere and know how all your departments are doing, you need OKRs and KPIs.

If you have enough shit to do to justify hiring a Chief of Staff or operational person on your team, you probably need OKRs and KPIs.

👀 Bonus: if you’re the CoS or ops person reading this, congrats! It’s probably time to implement something like this if you’ve already been hired.

How often do I audit OKR and KPI progress?

Ideally, once every two weeks (bi-weekly) at minimum.

This should take place during the ELT meeting with all the key stakeholders. Each stakeholder will be responsible for KPIs, and it’s their responsibility to report on how things are going. This also creates an opportunity for leaders to sync with other leaders and share what information or resourcing they’re missing to achieve their KPIs.

You can make this a very quick, painless process by having each person prepare ahead of the meeting. Try following this template to make this as easy as possible.

Ideally, every person should write whether their OKR/KPI is On Track, At Risk, or Behind.

• On track is straightforward.

• At Risk is if they’re about 1-2 weeks behind.

• Behind is if it’s more than 2 weeks behind and in the danger zone of being missed.
  

How often should I refresh OKRs and KPIs?

General cadence is once a quarter.

Usually, towards the end of a quarter, you will want to set new ones for the next quarter, and you will conduct a postmortem or retrospective on what happened in the previous quarter’s OKRs and KPIs.

During the meeting, cause each person to write what they think went well in this planning process, and what they think could’ve been better. Timing, scoping, objectives, and DRIs should all be considered with a score 1-5, where 3 = meeting expectations.

When should I choose new OKRs and KPIs?

These should be done by the leadership team, either during a strategic offsite, or in a single meeting towards the end of the quarter.

The larger your team grows, the more likely you’ll need a facilitator to help keep the team on track and cause them to do pre-work ahead of the meeting.

Additionally, each department head should conduct an overview of department-specific OKRs/KPIs and how they ladder up to the larger company OKRs with their teams, so the ICs are all on the same page on what matters and why.

If this doesn’t get done, you risk creating “siloed successes” that don’t actually move the company forward.

Should we be hitting all OKRs every time?

…no. If you’re hitting ALL of them, they’re probably too easy. If you’re not hitting majority of them, they’re probably too hard.

Most successful companies I’ve coached have about a 70% hit rate on their OKRs. That’s why prioritization via stack-ranking is so helpful - you can make the calls on which stuff will get pushed to the wayside if and when needed.

Ideally, the operator is the one who can help the CEO spot when OKRs are too easy or too hard.

Most CEOs I know shoot for outrageously ambitious goals that aren’t possible to achieve and lead to burnout for the whole team, but on the occasion, the goals aren’t ambitious enough. The Chief of Staff or ops person will know the best on how realistic it is to achieve what the CEO wants.

Good OKRs

👉 There should be two segments of OKRs: company-level and department-level.

The company-level OKRs are usually projects that require multiple departments to function with one another to reach the goal. It involves much more thoughtful teamwork.

Note: There are, on occasions, company-level OKRs that are entirely owned by one department. For example, “Achieving SOC 2 Type II compliance by September 30” could be entirely owned by Security or Ops, but might be important enough for it to be company-mission-critical.

From those company-level OKRs, you should then encourage each department head to declare what their department-specific OKRs will be. These are the things they promise to achieve in order to meet the company-level OKR.

OKRs can be qualitative or aspirational in tone, but they need to be observable or provable through your KPIs. The KPIs should be the quantifiable measurement on whether you’ve hit the OKR or not.

👉 OKRs should always have clear, unmovable deadlines.

Do not push the deadlines - they should be written in pen, or enter a database that is locked. You either hit those goals on-time, or not.

Of course, things will come up - but it is important to see when the original goal was set, and how often it moves. This gives you better data on knowing what the company is actually prioritizing.

👉 OKRs should have a clear owner.

This is the person who will own the outcomes no matter what. This person should usually be on the leadership team to take such a huge responsibility on.

Ideally, the CEO is the one who determines which leaders own which OKRs. Their Chief of Staff or ops person can help by identifying who would be best for owning the OKR based on both their hard and soft skills - how likely they can complete the OKR, and how collaborative the OKR has to be.

👉 Lastly, OKRs should be prioritized.

Not everything can be prioritized as “#1.” What happens when emergencies come up, and your department heads have hard decisions to make on what to prioritize and what to deprioritize?

Stack-ranking them in order of 1-3 will allow them to have the right information to prioritize accordingly, without having to loop you in constantly and ask you for permission.

Good KPIs and Actions

👉 The way OKRs are qualifiable, KPIs should be the measurement on whether you’ve hit the OKR or not.

Each OKR should have about 2-3 accompanying KPIs to determine how successful the initiative was. Those KPIs should define a quantifiable metric that is an easy yes/no answer on whether the initiative was achieved or not, with a clear deadline and tied to a business outcome that matters.

👉 Each KPI should also have a clear owner.

The worst is when there’s a really important task to get done, and everyone thinks someone else is doing it.

Without a clear owner, KPIs become "everyone's responsibility" which usually means "no one's responsibility.”

The way OKRs have clear owners, KPIs should too. Sometimes, they are the same person. Other times, it makes sense for the OKR owner to delegate specific KPIs to members on their team.

For example, if a CTO owns an OKR, they may choose to assign a KPI to the Head of Product, and another KPI to their Tech Lead. At the end of the day, the CTO is still responsible for the overall performance of the OKR, but this helps them get the individual nodes working without having to be everywhere all at once.

Write a clear owner’s name next to each KPI.

Whenever possible, the OKR owner should check with the KPI owner in advance and make sure they’re bought in. But if you’re the exec assigning it, own the delivery even if you have to delegate accountability fast.

The KPI owner should be accountable for tracking progress, reporting on status, and driving necessary actions to achieve the KPI during the aforementioned bi-weekly leadership team check-ins.

Note: They don't need to do all the work themselves, but they need to be the person who loses sleep if the KPI isn't met. And it’s their head on the chopping block at leadership team meetings if things aren’t done.

👉 KPIs should always lead to Action Items for each department.

Because KPIs are usually owned by department heads, they’ll be the best equipped person to pass work down to the Individual Contributors on their team.

These Action Items should be specific tasks that need to be completed by a designated due date in order to hit the KPIs. I recommend tracking them in your Master Task Board for full visibility.

Or, you can check out my playlist on how to use Asana to track your action items here.

For example, if a KPI is: “Increase customer retention by 15% by end of Q3”…

Action Items might include:

• Create customer feedback survey

• Implement new onboarding flow

Each Action Item should have a clear deadline and owner, just like the KPIs above them.

A Real-World Example:

Pricing Strategy Rollout

🏢 Company X Context

Company X is a B2B SaaS startup growing fast in the workflow automation space.

They’ve been getting crushed in mid-market sales cycles because their pricing is too rigid and competitors are undercutting them. Win rates are dropping and sales is getting loud about it.

Leadership agrees it’s time to rework pricing.

Step 1: Setting the company-level OKR

“Launch competitive pricing model for ProductX by September 30, 2025.”

This OKR is chosen because pricing is now a clear strategic blocker. Fixing it impacts win rates, revenue growth, and retention.

Step 2: Choosing the company-level OKR owner

The CEO assigns ownership to the VP of Product. They decide not to assign it to Finance or Sales, because:

• Product owns how pricing is packaged, surfaced, and toggled inside the product

• The VP of Product has cross-functional pull with both stakeholders in Sales and Finance

• They’ve previously shipped large initiatives across teams

The Chief of Staff supports the CEO by recommending this owner based on the initiative’s scope, dependencies, and the VP’s track record for collaboration.

Step 3: Choosing the company-level KPIs for the OKR

To measure whether this pricing revamp was successful, the VP of Product works with RevOps. Together, they decide these are the smartest KPIs to measure:

• Maintain pricing within 2% of top 3 competitors

• Achieve 85%+ win rate against direct competitors on key deals

• Keep gross margins above 65% post-rollout

These metrics are quantifiable, tied to business impact, and pass the “stranger test” (if a stranger reads these KPIs, they know exactly what’s going on and what they’re trying to measure.)

⚒️ Product Team OKR

“Enable dynamic pricing based on real-time competitive data”

• Build automated competitor price tracking system by Aug 1

• Launch dynamic pricing engine in ProductX by Sept 15

• Owner: Director of Product

💰 Finance Team OKR

“Ensure pricing changes maintain gross margin targets”

• Model margin impact across 3 pricing tiers by July 30

• Launch real-time margin tracking dashboard by Aug 15

• Owner: FP&A Lead

📞 Sales Team OKR

“Enable sales team to confidently sell new pricing model”

• Document competitor pricing on top 20 mid-market deals by July 30

• Train reps on new pricing battlecards by Aug 30

• Owner: Head of Sales Enablement

⚒️ Product Team Actions

• Finalize list of top 3 competitors to track pricing against (Due July 5)

• QA automated scraping tool with Eng (Due Aug 10)

💰 Finance Team Actions

• Sync new margin model with Stripe billing backend (Due Aug 1)

📞 Sales Team Actions

• Interview top 5 reps to collect pricing objections (Due July 15)

• Deliver pricing enablement session (Due Aug 25)

💡 Here’s a list of the resources mentioned above! 👇️ 

• Coaching Founder: Weekly memo template

• Coaching Founder: Master Task Board Template

• Youtube video: Asana as an agreements tracker

Want more operational content?

Check out Coaching Founder for over a dozen free, downloadable Notion templates to use at your company, and tons of write-ups on how to level up your execs, your teams, and yourself.

About Regina Gerbeaux

Shortly after her role as Chief of Staff, then COO, she opened her own coaching practice, Coaching Founder, and has worked with outrageously talented operators on teams like Delphi AI, dYdX, Astronomer, Fanatics Live, and many more companies backed by funds like Sequoia and Andreessen Horowitz.

Her open-sourced write-ups on Operational Excellence and how to run a scaling company can be found here and her templates can be found here.

She lives in the Pacific Northwest with her partner Lucas and dog Leia, and can be found frequenting 6:00AM Orangetheory classes or hiking trails nearby.