The End-of-Year Playbook for startup founders

As the year winds down, it’s time to reflect on what’s behind us and plan for what lies ahead. We’re not big believers in the clichéd “New Year, New Me” mantra. Maybe that’s just our internal northerner talking — when January through March feel like a never-ending ice bath, it’s hard to muster enthusiasm for grand resolutions. But while people may not need a “new you” in January, your startup can definitely benefit from some fresh focus as you close out the year.

Reflect, recharge, and reboot

Think of it as an opportunity to take a deep breath: customers are busy with their own year-end chaos, and investors? Well, they’re probably skiing in Aspen. Take advantage of this lull to regroup, recalibrate, and reimagine the road ahead.

How to conduct a startup end-of-year review

An end-of-year review isn’t just a corporate formality — it’s a chance to figure out what’s working, what’s not, and how to make next year your best one yet. Here’s your guide to wrapping up the year with clarity, intention, and maybe even a few laughs.

Step 1: Gather the troops

Decide on a time and place for your end-of-year review. Whether it’s an in-person meeting or a cozy Zoom call, get your key players in the same (real or virtual) room. Bring along last year’s company plan, KPIs, and metrics — ARR, customer retention, satisfaction scores, or whatever your north star metrics are — and start with a big-picture view.

Then, dive into the details:

• Which goals did you crush?
• Which ones fell short, and why?
• Were those setbacks within your control?
• What mistakes did you make, and what’s the takeaway?

Make this part honest but constructive. You’re not pointing fingers; you’re building a better game plan.

Step 2: Conduct an annual post-mortem

Think of it as a startup autopsy, minus the grim vibes. Evaluate the highs and lows:

• Wins: What’s worth celebrating?
• Losses: Where did things go sideways?
• Learnings: What surprised you this year?

Consider involving your wider team (beyond just the leadership). Sometimes the best insights come from unexpected places. Did your customer support team notice an uptick in complaints about a specific feature? Did your sales team struggle with a particular segment? These nuggets can shape next year’s strategy.

Step 3: Analyze the runway

Time to dig into the numbers. Startups run on a mix of ambition and cash, so let’s figure out how much of both you’ve got left:

• Revenue: What did you generate this year? How does it compare to your projections?
• Margins: Are you squeezing enough value out of each customer?
• CAC vs. LTV: Are you spending wisely to acquire customers?

For pre-revenue startups, the question is even starker: How much cash is in the bank, and how long will it last? Don’t just plan for the best-case scenario — run numbers for a “what-if-we-hit-a-speed-bump” case too. Remember: optimism is great for pitching; realism is better for planning.

Step 4: Set next year’s financial plan

Use your newfound insights to shape your 2025 financial strategy. Key areas to focus on:

• Headcount: Do you need to hire more, or should you prioritize efficiency?
• Sales Goals: What’s realistic, and what’s a stretch?
• Cash Burn: When will you need to raise again?

You’ll also want to update your options pool plan to ensure you have enough stock options for hiring, retaining, and rewarding employees.

Step 5 : Update your investors 

Forget the fruit baskets. This year, give your investors something they’ll actually value: a killer year-end update. Share your progress, key wins, and a sneak peek of what’s ahead. This isn’t just about transparency; it’s about keeping them excited about your journey. Whether you’re raising next year or not, maintaining strong relationships now will pay off later.

Step 6: Celebrate the wins

Startup life can be a relentless grind, and morale can dip if you’re not careful. That’s why it’s essential to pause and celebrate your achievements, big or small:

• Hand out holiday bonuses if your budget allows.
• Host a team dinner or a pizza party (because nothing says “startup” like tasty takeout).
• Organize a Secret Santa exchange.

Let’s not forget the driving force behind your startup — your team. The year-end is a perfect time to show your appreciation for their hard work and dedication. Consider giving them some well-deserved time off to recharge and come back refreshed for the new year. Moving at startup speed is exhilarating, but it’s also exhausting, and people can only sustain that pace for so long. While other companies and vendors are on holiday, take the opportunity to do the same — for your team and for yourself.

Step 7: Align and set goals for the next year

Start with your company’s big-picture vision and work backward. What do you want to achieve in 2025? Break it down:

• Company-wide Objectives: Revenue targets, market share, product milestones.
• Team Goals: Smaller, actionable objectives that ladder up to the broader mission.

The key here is alignment. Every department, every individual should know how their work ties into the bigger picture. That’s how you turn a scrappy startup into a well-oiled machine. 

Final thought: Remember personal wins, too

Your startup’s success isn’t the only measure of progress. Did you take a bold risk this year? Learn a new skill? Overcome a fear? Even if your company didn’t hit all its goals, you probably grew as a founder — and that’s worth celebrating too.

Here’s to an even stronger 2025!