Where to start… 

The first sixty days are a damn mess. You wouldn’t have been hired if everything was going perfectly.

We are going to start with a simple fact. The first sixty days matter. A lot. We will keep this article short and sweet so that you can get on with it.

If I haven’t made it clear, I’ve been there when I uselessly rebuilt an operating model, screwed up an operational meeting, blatantly ignored a pivotal conversation about metrics, or tried to be a strategic CFO without knowing anything. It’s surprising how the best intentions can lead to a lot of worthless work. 

Here is the advice that I wish I had followed when I started. I’m putting the plan in the know-and-deliver format (things to know, things to deliver). The principle behind this is to ask questions and test yourself. This builds off the psychological insights that we all learn better by doing and testing. This guide will get you up to speed thoroughly. The key questions you should be able to answer at the end of two months:

• Where is all of the cash going today, and where will it be going in three months (down to the cent)?

• Have I earned people’s trust?

• What are the biggest three priorities that I must solve in the next ninety days?

• What is the story of the business?

Note, none of that involves bringing a playbook, saying you are performing an audit, ignoring the business. That’s just the wrong approach and you will immediately lose respect from key team members. Without further ado, here’s the plan:

Know: Things to review.
Deliver: Deliverables to hand over to the exec team.

The keys to success?

1. Buy a notebook. Take notes instead of actions. Separate them into risks, opportunities, priorities that you review at the end of every two weeks.

2. Be straightforward and thorough. You need to earn the credibility. Don’t assume. Rather, ask relentless questions (nicely). People love to talk, and often people’s first response doesn’t paint the full picture, so understanding the ‘why’ does both you and the asker a service.

3. Deliver 2-3 quick wins. In two months, you need to deliver at least a couple quick wins. This gets people excited for when you are full time and avoids the dreaded question ‘still onboarding?’

Let’s go.

1. Foundational tasks (Days 1–14)

First day. Slow down. Focus on the basics for the first two weeks. You need to be listening, taking notes, and diving into the essentials that will earn you trust. Your first deliverable is to create a cash flow projection. To start:

• Get to know your team. Talk to each person individually. Take the team out for lunch. You want to establish this will be an improved era.

• Get a handle on cash. This is your job. Focus deeply on it. Nobody will know or care about it more than you. Where is it and how is it being used?

• Review the budget. It was made for a reason (even if you don’t believe it). Understand the trade-offs made between the lines.

• Use the product. Use it to actually do something (not just demo). If you want to ingratiate yourself to the team, knowing what 75% of the team works on all day is absolutely essential. It’s amazing how many people don’t do this and how quickly you lose face with the team if you don’t.

• Review the close process. Go through who does what during close. Let the first process close without any intervention (if the timelines add up) and then block out a day to critically dive through each line by line as a check.

• Deliver: Cash flow statement. 3-month projection with solid runway modeling. This tests your handle on cash and the budget.

It is your first two weeks. These provide a strong baseline for every other analysis you will do going forward and get your finger on the pulse quickly.

Tip: Give people a chance to confess to mistakes made and accept them as things in the past. You aren’t judging previous performance and you want to discover the skeletons in the closet as soon as possible.

2. Analysis and improvements (Days 15–30)

Okay, now it's time to get deep. Really deep. Zoom into the details so you can understand where the numbers are coming from. Tasks:

• The Customer Journey. Follow a sample company. Know how marketing targeted, sales closed, RevOps tracked, finance billed, customer success onboarded, and how they are using the product. Imagine the customer.

• Key metrics review. You need to know what the basic definitions of your SaaS metrics are. Are you being aggressive or conservative, why?

• Product Usage. Find out how people are using the product. How many aren’t. What is the roadmap looking like, and what’s the next big feature release.

• Customer Success. How long does it take to get people on the platform and how many then upsell or churn?

• Executive Chats: Hold individual meetings with each individual executive. If possible, have them share their relevant strategy documents so that you can review and have questions before the meeting to save you both time.

• Deliver: Monthly Close Report. Budget versus actuals for the current month and YTD results. Present it to the CEO on the first day of the month. Go all in.

At one month end, you should be able to have detailed knowledge of your customers and an overview of your financials. That is a great start.

Tip: There will be many issues you want to solve. List them, forget about them, and then come back to them at the end.

3. Ramp up on the day to day (Days 30-45)

Once you have passed the first monthly business review, it is time to start doing your job. Slip slowly into the day to day and ensure you have the setup in place to be effective. These two weeks:

• Start checking in with the CEO. Schedule regularly. Bring an agenda.

• Lead the MBR. Take the helm. By now, you would have had several management meetings. Don’t change anything in the process until you feel it's absolutely necessary.

• Investigate report use. Have your team identify all the primary reports being used. Then, go over to the particular team in question and ask whether they know the numbers. It’s a quick way to see how people use or don’t use information in their role.

• GTM Analysis. This is pretty explanatory. But make sure you are focused on all teams in the GTM motion from strategy to outbound to marketing to AEs.

• HR & People Analytics. This will strongly inform your budget and assess how deeply the team is looking at people's performance metrics.

• Coffee chats. Take people out to coffee. This could be a manager, an AE, a CSM. You just want to meet people, get a feel so they know your face outside of the executive level.

• Deliver: One quick win. By now, there must be something you can help with from all these chats that take little time but help people. Do one of these.

• Deliver: List of report. Pick all the reports that are being used. Have them automatically generated to your email (or slack) on a regular basis for your review. This makes it easy to get an ongoing sense of the business.

• Deliver: Reporting overview. Pick all the reports you want to change, why, and the criticality. There is nothing you need to do now, but it will test your sense of how people are using data.

You have now reviewed nearly every function of the business. By the end of this month, you should be waking up to a great overview of the business so you can keep your pulse and expand on what you learned.

4. Strategic initiatives (Days 45–60)

Okay, now maybe you can contribute something strategic by merging your instincts and gained knowledge over the last 45 days of intense onboarding. Now it’s time to:

• Board review. Review the board decks from the previous several years. Correlate this to what you have been hearing/seeing to see how good the company is at doing “what they promised.”

• Assess the tech stack. Review the tools. Prioritize if you need to make it easier or fix any processes.

• Craft a narrative. Create a narrative for the company that you have now seen. So, how would you summarize the strategy and progress over the last three years? Test it out with another exec.

• Define your role. This is the time to define how you can be effective. Your roles and responsibilities, your deliverables, your interactions across the team.

• Board Chats. You want to know your board. Take a call for 15 minutes and get their take on the company and your role. This will greatly help you navigate the board room in your future presentations.

• Deliver: Another quick win. It’s a nice habit to get into, at least one win every two weeks.

• Deliver: 3 Top Priorities. Take everything you have done. Summarize it into the top three things you want to focus on. Present it to the executive team.

• Deliver: 3 Top Risks. Same as the above. Be upfront and honest with the risks. Some you can mitigate, others you will have to live with.

• Deliver: Investors email. It’s time to start sending the investor updates. You know the board and the numbers. It’s a great way to make sure you are aligned with the CEO to review it with her before.

That’s it. Now the fun starts. 

Tip: Note that a great start-off point from here is updating the forecasting and budgeting process into a rolling budget if that hasn’t been done.

In conclusion

The first sixty days will always be a whirlwind. You want to balance an overload of new information, with being useful, with maintaining the excitement that comes with new leadership. This plan is a start. Customize it as appropriate.

Here’s to the best intentions and great results.