The First 90 Days as a Head of Product

Welcome and Introductions

Rina Alexin | 00:00–02:20 Hi everyone! We’re going to get started shortly. As you join, please share your name and where you’re calling in from in the chat—we love to know who’s with us.

Welcome to The First 90 Days as a Head of Product! I’m Rina Alexin, CEO of Productside and host of our Productside Stories podcast. I’m joining from sunny Miami, Florida, and I’m thrilled to be joined today by Christine Itwaru, Head of Product and Design at Vitally.io and formerly Head of Product Operations at Pendo.

Christine Itwaru | 02:21–02:45
Thanks for having me, Rina! I’m joining from Raleigh, North Carolina—where it’s hot and a little overcast but almost as warm as Miami. Excited for today’s conversation.

Rina Alexin | 02:46–03:20
This webinar will be more of an Ask Me Anything format. We’ll talk through how to make the most of your first 90 days as a product leader, followed by audience Q&A.

At Productside, we’re an outcome-driven product partner helping organizations transform by developing product mindsets through tailored training and coaching. Every engagement is led by seasoned experts.

Poll #1 – Who’s in the Room?

Rina Alexin | 03:21–04:00 Before we dive in, let’s take a quick poll to see where everyone is in their career journey—product managers moving into leadership or existing leaders looking to recharge.

Rina Alexin | 04:01–04:40
Looks like 43% of you are PMs ready to take the next step into leadership, and about 40% are already in leadership, looking for new strategies. Perfect mix for today’s discussion!

Christine’s Journey into Product Leadership

Rina Alexin | 04:41–05:00 Christine, tell us—how did you first get into product management?

Christine Itwaru | 05:01–07:00
I fell into it—like many of us do. I was working in product marketing at an investment bank when I realized I cared deeply about how people used our tools. Watching users struggle made me rethink how we designed products.

One night, I mocked up a redesign of one of our widgets. The next day, my boss implemented it—and the user loved it. That was my “aha moment.” I realized I wanted to make products that fit into people’s lives instead of forcing people to fit into products.

Transitioning to Product Leadership

Christine Itwaru | 07:01–10:00 My move into leadership came almost unexpectedly. After returning from maternity leave, I was asked to manage a small team. I wasn’t sure I was ready, but my boss believed in my ability to coach others. That support—and his advice to “pay it forward”—shaped my leadership philosophy.

Being a leader isn’t about control; it’s about enabling others. That’s what inspired me to step into product leadership—helping others build great products and grow in their roles.

Choosing the Right Organization

Rina Alexin | 10:01–11:00 Let’s talk about culture fit. Product leaders often leave roles within 2.5 years. How do you assess whether a company embraces a true product culture before joining?

Christine Itwaru | 11:01–15:00
I look for honesty. In my interviews with Vitally’s founders, they were transparent about what was great and what needed work. No sugarcoating. That honesty told me I was dealing with authentic leaders.

I also check whether the CEO is a product CEO. Are they ready to let go? Are they open to collaboration? These are key indicators. I ask directly: “How willing are you to shift ownership from yourself to your product leaders?” If they can’t answer honestly, that’s a red flag.

Preparing for Day One

Christine Itwaru | 15:01–17:00 Start before you start. A week or two before your official first day, reach out to peers—head of sales, head of CS, PMM, engineering leads. Build relationships early.

Those pre-start conversations will help you understand company goals and current challenges, so on day one, you already have context and can plan your quick wins.

Building Relationships and Quick Wins

Christine Itwaru | 17:01–22:00 Your first 90 days should be about people, not processes. I met nearly 65% of our 85-person company in my first month. Start with engineering, your closest partners, and then expand to other departments.

When I saw misalignment and information gaps, we created a Product Digest—a bi-weekly update summarizing what’s happening in product. We followed it with a short “Amazon-style” read-and-discuss session. Within a month, we cut meeting time in half because everyone was aligned.

Managing Up and Across

Rina Alexin | 22:01–25:00 I love that quick win! But how did you approach building relationships at the leadership level—managing up and across with the C-suite?

Christine Itwaru | 25:01–27:00
Be human first. I start by sharing who I am—my motivations, my life, even my quirks. Vulnerability builds trust.

We also do “User Manuals” on my team—short profiles with questions like “What motivates you?” or “How do you prefer feedback?” It humanizes the workplace and deepens understanding between peers.

Overcoming “We’ve Always Done It This Way”

Christine Itwaru | 27:01–29:00 You’ll always encounter people resistant to change. Instead of confronting it head-on, I ask: *“What’s different this time?”* or *“What has changed since the last attempt?”*

This turns hesitation into dialogue. It’s about co-creating solutions, not dictating them.

Building Credibility and Trust

Christine Itwaru | 29:01–31:00 Trust is earned by being transparent, data-driven, and outcome-focused. Always tie decisions back to company strategy. If you don’t have a defined strategy yet, co-create one with your CEO.

Data is your currency—use it wisely to influence and align.

Hiring and Developing Product Managers

Christine Itwaru | 31:01–35:00 When hiring PMs, start with your company’s current phase. Do you need builders, optimizers, or changemakers?

Look for PMs who thrive in your environment. Bring peers from engineering and CS into the interview process to test for collaboration and communication. Skills can be taught; mindset and adaptability can’t.

Q&A: Assessing Your Team’s Skills

Rina Alexin | 35:01–37:00 How do you assess gaps and team maturity when you inherit an existing team?

Christine Itwaru | 37:01–39:00
Talk to everyone personally. Don’t rely on others’ opinions. Observe how they think, communicate, and handle problems. Ask your manager for context, but form your own perspective.

Use the first few weeks to identify who can grow with the company and who may need new challenges or coaching.

Preparing for a Leadership Role

Rina Alexin | 39:01–41:00 Final question: What advice do you have for PMs interviewing for leadership roles—either externally or internally?

Christine Itwaru | 41:01–43:00
Start doing parts of the job before you get it. Demonstrate initiative, collect feedback, and use data to show your impact.

When you interview, share your plan—your priorities, how you’ll measure success, and the outcomes you’ll drive. That clarity builds confidence and trust.

Closing Remarks

Rina Alexin | 43:01–End Thank you, Christine, for your insight and honesty. And thank you to everyone who joined.

If you’d like to assess your team’s maturity, try our free Product Management Team Assessment—you’ll receive a custom report based on our Productside Blueprint and a complimentary 30-minute session with one of our experts.

Follow Productside on LinkedIn for upcoming webinars and insights, including our next session with Prashant Mahajan from Zeda.io on using AI for product discovery.

Until next time—keep leading with confidence, empathy, and clarity.