CPO Success Tips

Welcome and Introduction

Christina | 00:00:00–00:00:38
I’m Christina from the Dragonboat team and today we have Becky Flint, Dragonboat’s very own CEO, joining us as well as Rina Alexin, the CEO of Productside. We’ve got a really exciting conversation teed up today. So before we officially begin, just a quick word on Dragonboat. Dragonboat helps enable product leaders to accelerate their outcomes with a suite of products for outcome-focused roadmapping and delivery. So check out dragonboat.io slash CPO if you want to learn more.

Introducing Becky Flint and Rina Alexin

Christina | 00:00:39–00:01:10
Next slide, I’m going to hand this over to Becky to kickstart the conversation and to officially introduce Rina, our guest speaker for today. So I’ll let you take it from here, Becky.

Becky Flint | 00:01:11–00:01:40
Thanks, Christina. Good morning, good afternoon, wherever you are, and happy New Year. My name is Becky Flint. I’m the founder and CEO of Dragonboat, and with great pleasure, I’d like to introduce our guest today, Rina. Rina is the CEO of the Productside, which is a leading product education provider and more.

Rina’s Background and Productside Perspective

Becky Flint | 00:01:41–00:02:16
Rina has extensive experience as you can see in strategy and product leadership at many amazing companies throughout the world. Rina joined Productside with a focus on bringing transformation changes to organizations and arming product people with the right tools and skills to do great product management, so very on point on our discussion today. Welcome, Rina.

Rina Alexin | 00:02:17–00:02:50
Hi Becky, thank you so much for having me. I’m so excited for our discussion today. And a bit more to share about Productside, because I think that’s really going to help shape our discussion. Productside, yes, we’re an education provider, but what we really are is a little different. We believe that product management teams, in order for them to become truly effective, we need to take care of not just skills, we also take care of process and culture.

Role of the CPO in Product Organizations

Rina Alexin | 00:02:51–00:03:22
And at the head of any company’s product leadership is the CPO. So the person who is required and has the mandate of making sure that their teams have the ultimate chance of success. The CPO has to have the skills and knowledge to make sure that their teams are empowered and are operating in the context of an organization that understands and values product management. And so that’s why I’m really excited about our conversation here today.

Webinar Format and Discussion Themes

Becky Flint | 00:03:23–00:03:55
Right, well thanks so much for the context, Rina. And you know we had a brief check yesterday, and just for everyone joining us today, we typically have our webinars in a couple different formats. And today’s format is actually a lot more conversational. As you see, the topic is quite broad around how CEO and CPO can work together. And we’re going to cover leadership, outcomes, delivery, responsiveness, and tools.

Is the CEO Also the CPO?

Becky Flint | 00:03:56–00:04:25
Maybe we can start by talking a little bit about the CEO and the CPO. I think both of us have similar stories. There’s a lot of talk around do you need a CPO, do you not need a CPO, is the CEO the CPO? So let’s get that conversation started.

Rina Alexin | 00:04:26–00:05:01
I’ve heard it a number of different ways. In smaller companies, especially startups, the founder really should be the CPO. The CEO is the CPO. And there’s a really good reason for it. In early-stage companies, the product team needs to know where are we going, what is the vision, and that is really owned by the founder.

When Organizations Need a Dedicated CPO

Rina Alexin | 00:05:02–00:05:33
But when we come to organizations that are much larger, they’re scaling up, the CEO is still responsible for the vision, but they need to translate what does that vision mean for a product portfolio. And that is more than a full-time job. So once organizations become more complicated, usually there needs to be a really strong CPO.

CEO and CPO Relationship at Scale

Becky Flint | 00:05:34–00:06:06
There is definitely a transition point where the CEO hires a CPO, and then the question becomes how does the CEO work with the CPO? Because we see some companies go through that transition well and others not so well.

Rina Alexin | 00:06:07–00:07:09
When it doesn’t work is when the CEO is not mindful that once you have a CPO, the CEO is no longer the strongest voice in the room on product. The CPO has the mandate to think long-term about where the company is going, while everyone else is focused on the here and now.

Short-Term vs Long-Term Product Thinking

Rina Alexin | 00:07:10–00:07:44
Sales leaders are focused on this quarter. Support is focused on today’s problems. But the product organization needs to be thinking about the future. And when the CEO doesn’t reinforce that, that’s when the relationship starts to break down.

Scaling Product Portfolios

Becky Flint | 00:07:45–00:08:46
There’s also another type of company — companies that historically grew through sales and marketing and now realize what got them here won’t get them where they want to go.

Product-Led Transformation

Rina Alexin | 00:08:47–00:09:41
Those companies often need more than a leader — they need to change how they operate. They need to redefine what a product is, what a portfolio is, and how value is delivered to customers.

Portfolio Thinking and Organizational Design

Rina Alexin | 00:09:42–00:10:46
Companies organize portfolios differently. Some organize around customer journeys, some around platforms. It depends on how they deliver value.

Common Challenges Across Product Organizations

Rina Alexin | 00:10:47–00:15:07
When we analyzed a decade of our engagements, we found three consistent challenges. One is poorly defined roles and responsibilities. The second is missing strategy alignment between business and product. And the third is stakeholder misalignment.

Building Trust Between CEO and CPO

Becky Flint | 00:15:08–00:18:24
Trust is something we hear about constantly. How do you build trust with the CEO, with stakeholders, and with your team?

Strategy, Data, and Trust

Rina Alexin | 00:18:25–00:21:01
Trust is built by setting expectations and delivering on them. CEOs and CPOs must be aligned on business priorities, KPIs, and strategy. Roadmaps should be communication tools, not release plans.

Executive Alignment and Decision Cost

Becky Flint | 00:21:02–00:24:06
If there’s confusion at the top, there will be confusion at the bottom. Strategy conversations need to have cost and consequence, otherwise everything becomes a priority.

Saying No as a Product Leader

Rina Alexin | 00:24:07–00:25:39
A good strategy enables teams to say no, and to explain why they’re saying no.

Product Data and Operating Systems

Becky Flint | 00:25:40–00:31:14
CPOs need a centralized view of customer value, business outcomes, and delivery costs. That’s why product operating systems matter.

Learning Models and Product Outcomes

Rina Alexin | 00:31:15–00:33:53
Great companies understand value, operating models, and learning models. Tools should amplify strategy and learning, not replace them.

Strategy vs Delivery Tension

Becky Flint | 00:33:54–00:40:21
When strategy is unclear, teams default to delivery. Outcomes matter more than output.

Discovery, Leadership, and No Shortcuts

Rina Alexin | 00:40:22–00:42:56
There are no shortcuts. Tiny acts of discovery and strong leadership are required.

Closing Remarks

Becky Flint | 00:42:57–00:43:27
Thank you, Rina, and thanks to everyone who joined. We’ll follow up with resources.

Rina Alexin | 00:43:27–00:43:45
Thank you so much. This was a great discussion.