As Product leaders, you have to build trust with CEOs and founders, align on vision and strategy, stay focused on the customer’s problem, and effectively navigate misalignment to ensure your product has the greatest chances of success right out of the gate. 

But how do you tactically achieve all of that? Tamar Yehoshua, former CPO at Slack and Partner at IVP, Anneka Gupta, CPO of Rubrik, and Noam Lovinsky, CPO of Grammarly, shared practical advice at SaaStr Annual from the trenches so you can build great products and great teams all at once. 

And see everyone at 2024 SaaStr Annual on Sep 10-12 in SF Bay!!

Building Trust as a New CPO

As a CPO, the most important thing you have to do is build trust with your CEO or founder. It’s obvious, but how do you do this? Noam jokes that the best way to get there is to immediately start making decisions as though you already know everything. Of course, that’s not true, and it definitely won’t help you warm up to your new founder or CEO. 

Phase One: Notetaker

Noam’s real advice is when you first come into a CPO or Product Manager role, you have to be a notetaker. That’s your role, figuratively and literally. You have to carry the water, take notes at meetings, and help the teams on process to make them better at operating and executing. Your role is to listen and gently help the team be more efficient at what they’re already doing. 

Phase Two: Team Evangelist

Make sure everyone to the side of you and above you knows what your team is doing, your goals, and your strategy so they can work together. 

Phase Three: Goal-Setting

Stage three is about setting and creating strategy together with the leadership team. This three-phase arc starts in listening mode, not decision-making mode, focused on accelerating the team in what they already do best. Eventually, you can set some goals and strategy and build together. 

Ask The CEO How They Want to Be Involved

CEOs want to be involved in the product. A foundational part of starting as a Chief Product Officer is to build that relationship with founders and ask them directly how they want to be involved. What roles do they want to play? 

To build trust, you have to figure out where the gaps are and how you can add value in small ways. Don’t try to push your agenda into that working relationship. Sit back and listen to their role, and figure out how to integrate that to push the company forward. 

It can be a challenging relationship, and you have to get it right. The only way to get it right is to spend a lot of time together and not shortcut the onboarding piece of these different phases. 

When to Hire Your First CPO

You have to evaluate when you need your first Head of Product. It may not be a CPO, Anneka says. That’s a very senior role. If you bring in a really senior person too early, they may want to take the reigns before you have enough product market fit, and they may try to take on the CEO role. 

If you’re pre-product market fit, you may want to be at the reigns driving product. When you’re breaking, can’t spend the time and have too many customers, then maybe it’s time to bring in a Product Manager or a Director of Product Management. As you scale and need someone to prioritize your roadmap and build the organization, then you bring in the high-powered leader who can also build structure around how to strategize for a second, third, and fourth product. 

How to Align Vision and Strategy in the Early Days

Aligning on vision and strategy begins with figuring out the problem you’re obsessed with and determining how well you understand it. How stable and enduring is that problem? 

We all get solution-focused too quickly, and solutions are shiny objects. It’s easy to get excited about what you can build, but you need to identify the real painkillers for a business. To align on vision and strategy, you need to internalize the founder’s understanding of the problem you’re trying to solve and make sure it’s a problem worth solving. From there, solving the problem becomes easier. 

Keeping Everyone Focused on the Problem

Shiny objects are attractive, so how do you keep these conversations with the founder and your team focused on the problem? Keep asking why and ask yourself what you want to be true about the world if you succeed. 

You want to look at those answers and be grounded in the problem you’ll solve for the customer regularly and have conviction. What happens when you’re not aligned? 

There may be times when there’s struggle on the executive team about where you should go. Often, this is when the CEO isn’t the founder. It sometimes manifests with misalignment on where to make a new acquisition or which avenue of growth to focus on. 

Anneka approached a situation like this by shepherding conversations, taking the emotion out of it, and focusing on the customer’s problem. Some questions they asked themselves were: 

  • What is the urgent and important customer problem to solve? 
  • What evidence do we have? 
  • What options do we look at? 
  • What is our ability to solve the problem? 
  • What is the amount of investment to solve the problem? 
  • Are there other leaps of faith to build a successful business around that? 

When you lay it out on paper, it’s easier to say these are the reasons why and get to a place of finding the highest probability path forward. Your job as CPO isn’t to make everyone happy but to get to a decision that’s right for the company. 

Tactical Ways to Ensure Your Roadmap is Clear

You’ve built trust with the founder or CEO, have strategy and vision, and a focus on customer problems. How do you deal with the reality of the roadmap? Once you start building the roadmap, things change. How do you stay focused on the customer problem and tactically ensure the roadmap is clear? 

Depending on the stage and maturity of your business, how far can you realistically forecast, and how do you want to set up your process around that? 

Noam gives an example from Grammarly. It’s a very large business with almost a thousand-person team in a dynamic space. You can’t plan yearly here, and he couldn’t confidently tell you what would happen at the end of the year. 

When he first joined, there were foundational LLMs, and they were doing everything on top of them. Then, two months later, there were open-source LLMs that were just as good, and they could build everything on top of them. 

You can set longer-term goals and know where you want to be, what strategy could get you there, and how to differentiate in the space, but tactically, how far ahead can you forecast? Maybe six months and then a month plus one roadmapping? You can do rolling roadmaps even with a big team. 

Since you’re planning for shorter horizons, you can use shorter planning windows to do that. You don’t have to do what everyone says in the product management books. 

What Metrics Matter Most for Your Roadmap

As you put your roadmap together, what should you look at? What metrics and outcomes matter most? At Rubrik, a fairly late-stage company with multiple products, different products are in different stages of their lifecycle. 

Some mature products are heavily adopted, and newer ones’ first versions came out six months ago. So, when looking at metrics for success, you have to look at what’s driving the business forward. 

Each product will look different. For larger products, you could look at: 

  • Total ARR. 
  • What goals are around new ACV? 
  • How does your roadmap align with those goals? 
  • Where is the growth coming from? 

For earlier-stage products, it’s about getting initial customer traction and strong feedback. Do you have strong product market fit? If not, what will it take to get there? 

Anneka runs quarterly business reviews for all parts of the product portfolio, but how they look at and evaluate each product changes because the measures of success will be quite different. 

Build vs. Buy — How to Prioritize Resources

One of the biggest challenges for a CPO is prioritizing resources, which begins with deciding whether to build or buy. Can you supercharge your business by buying? Rubrik recently made a thoughtful acquisition, so let’s look at its decision-making process. 

The journey started about a year ago when they realized they serviced customer data on-premise, in the Cloud, and across SaaS apps, yet a lot of their DNA was from the on-prem world. They asked themselves, “If we want to achieve our vision of securing data across all of these areas where data lives, what’s standing in the way of accelerating in the Cloud?” 

They saw an opportunity to bring in a company with the right DNA and complementary capabilities to accelerate that path. So, they explored almost every company in this emerging space and researched how they would fit into their portfolio. 

From there, they found a target where the architecture was complementary, the team was strong, and there were good bones to build off of. The acquired company’s biggest gap was GTM skill, which Rubrik was strong in. 

Acquisitions aren’t always so methodical, but ideally, an acquisition should dramatically accelerate your roadmap. 

How to Deal with Salespeople Who Want to Implement Something Right Now

Build vs. buy is one thing, and anyone in Product knows what it’s like to have a salesperson come in and say you need to implement something right now. How should you deal with this as a Product leader? 

The first step is to be empathetic. Imagine yourself in their shoes, or actually walk in them and see what they’re running into. We can often be analytical and say, “Quantify that for me,” or, “What portion of pipeline is at stake?” 

A lot of sales doesn’t work that way. They’re out there pitching and having conversations, and there are holes in the conversations that stop the deal. You have to be the salesperson in a Product role to do a good job. Good product marketing means going in there and doing product marketing. Being good at sales means doing a little of the sales job.

If you say no to the sales team and that’s causing a problem, there’s usually some underlying issue, like a lack of confidence in your overall strategy. Product Managers at all levels need to be meeting with customers. If they aren’t, they can’t be empathetic. 

When Transformational Tech Comes Along, Like AI

Sometimes, transformational technology comes along, like AI. You’ve got a roadmap, and you’re balancing everything, and that technology blows up your roadmap. Do you stay focused or pivot? 

It depends. When you’re in a zero-to-one product development mode, the thing you should be optimizing for isn’t necessarily outcomes. It’s learning. The faster you learn, the faster you get to confidence, and the sooner you win. 

In more scaled products, you’re not always optimizing for the learning. You’re optimizing for a metric or outcome. But when you have a plan and an LLM punches you in the face, you no longer have a plan and must go back through the zero-to-one discovery process to figure out if you can use this new tech or platform to accomplish your goal. 

You need to have some portion of your team who isn’t optimizing for the win yet is oriented to product development. 

The Best Way to Communicate Your Vision

Where do you want to be as a company, and what are the existential risks you see in the market stopping you from achieving that vision? Asking those questions creates clarity. Then, you identify 3-5 things to get there and repeat them in every forum for the next however many years. Repetition until you’re bored. 

How do you communicate that vision to your team, peers, and customers? 

By painting a story. The main job of a CPO is Chief Storyteller. You have to visualize and manifest the journey and ensure everyone has that movie in their head. Present and update that vision regularly as you learn so everyone has that story in their head week to week, quarter to quarter, and all day-to-day decisions are aligned towards that. 

People remember stories. 

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