The Product Leader’s Playbook 2026

Welcome, Webinar Setup & Audience Icebreaker

Kenny Kranseler | 00:00:00–00:03:05
All right, welcome everybody. Um, we are going to start in a couple of minutes, but you are in the right place if what you’re looking for is the panel discussion led by Productside on our playbook for all things AI for 2026. So, welcome.

And if you’re bored while you’re waiting for us to start our webinar, you can use our chat box to answer my audience icebreaker question. Just put in your favorite holiday movie, and our panelists can answer that one too. So, just put in your favorite holiday movie.

I can put in mine too.

I figured someone would put Die Hard because there’s always the controversy of is Die Hard a holiday movie, and I’m just like, get over it. Of course it is. It’s a passionate argument.

Love Elf. Yeah, Ashley. Really? The holiday. What else we got? Um, Home Alone. I like that one.

Claus. I haven’t heard of that one, Katherine.

Yeah, it’s like a relatively new movie, probably two to three years ago that came out, and I just watched it on a whim. Um, but yeah, I thought it was really sweet, and it’s about the origination, you know, one version storytelling of where Santa Claus came from, and I thought it was just a very cute, sweet, very nice storyline.

Nice. Excellent.

All right. Anybody joining us lately? We’re using the chat functionality to put your favorite holiday movie.

And if you put A Christmas Carol, you have to put which version. I like the old one with Fred what’s-his-face from the 50s or 60s. The old black and white one.

Yeah, I agree. I agree, Connie.

All right, we’ll give another minute or two for folks to show up and find their way to our Zoom webinar.

Scrooged. Ain’t Bill Murray wonderful?

Yeah. Just can’t recall how much of that would hold up to a modern sensibility of what is good for children to watch today. Probably not.

Anybody watched Caddyshack? It’s the same thing. It hasn’t aged well. But I can still lean on the joke of the chocolate bar in the pool. People can relate to that.

There you go. That’s true.

And a dancing gopher still gets me excited.

Official Welcome & Webinar Context

Kenny Kranseler | 00:03:05–00:05:25
All right. Well, I think we’re probably at a good point for me to at least start things going. Thank you all for sharing your favorite holiday movie.

If you are looking for our webinar on The Product Leader’s Playbook for 2026, where we talk about things like AI and multimodal experiences and sort of the new customer expectations in that world, you’re in the right place.

You’re in for a fun and exciting hour of hopefully interesting banter and discussion that will get you excited.

With me, I am Kenny Kranseler. And with me, I’ve got three fabulous, well-informed panelists in the area of AI and product management.

I’ve got Ashka Vakil, who is the Senior Director of Product Management at StrongDM. I’ve got Scott Jones, who is the co-founder and CEO of a company called Realeyes. And I’ve got Katherine Man, who is the Executive Vice President of Product Marketing at HubSpot.

We cover all corners of the country right now, with Ashka from San Francisco, Scott from North Carolina, Katherine from Boston, and me splitting time between Seattle and Southern California.

So welcome everybody.

About Productside & Webinar Housekeeping

Kenny Kranseler | 00:05:25–00:09:10
Before we dive into the topic, I want to share a little bit about Productside, the sponsor of this webinar, and give you a little bit of who we are and what we do.

Productside is a company focused on product management and product management teams and managers, and all those trying to make the world better for product managers because we know how hard it is to deliver products that people not only use but really love.

Whether it’s figuring out how to align stakeholders, figure out what customer needs are, or manage those endless backlogs that product managers run into, we’ve sort of seen it all.

We’re really here to be your outcome-driven product partner, where we’re not just providing solutions, but we tailor solutions to the unique challenges the companies bring to us, enabling strong transformations from strategy to execution.

We’re really with you every step of the way, and we do it in a way that’s focused and tailored for your specific needs.

The first question I usually get is, can we ask questions? The answer is yes. There are two ways to do that. You can either do it in the Zoom chat or Zoom Q&A, which I’ll keep a monitor on.

If there are questions along the way, I may throw them at our panelists. If not, we may have a little bit of time at the end of the session to do some questions.

And the first question I usually see is, can I watch the recording later? And the answer is yes. We’ll send everybody a link to this webinar afterward.

I encourage you all to connect to Productside on LinkedIn. We have a special LinkedIn community that’s more than just a page. It’s a place to build a community, share best practices, and connect with other product leaders.

Panel Introductions Begin

Kenny Kranseler | 00:09:10–00:10:30
Without further ado, I want to give our panelists a chance to give a more detailed explanation of who they are and what they do.

Ashka, can you give a little bit of background on who you are and what you do?

Ashka Vakil | 00:10:30–00:13:15
Thank you, Kenny. Hi, Ashka here. I’m excited to be part of this panel and looking forward to the great conversation we have planned for you and of course your engagement.

A little bit about myself. I’m currently a Senior Director of Product at a company called StrongDM. I lead both product and design teams, and I’ve been in the industry for 20 plus years, starting my career as an engineer and then moving into product management.

I’ve worked primarily on enterprise products all through my life, both as an engineer as well as a product leader. And currently in my role, I think about AI a lot, but overall the balance between friction, security, and user experience.

StrongDM Overview

Ashka Vakil | 00:13:15–00:15:05
StrongDM is in the space of identity security. I don’t know how many of you are familiar with the space, but we look more from an identity perspective. It’s not about access like who has access to what, but really looking at real-time data in terms of whether you have a breach happening, whether you are a user who had just accessed certain resources and you did something that you shouldn’t do, then you shouldn’t really get access.

So it’s really more around authorization, and our focus has been on both human and non-human identities, how to securely have them connect to the infrastructure and the resources.

Scott Jones Introduction (Realeyes)

Scott Jones | 00:15:05–00:19:10
Sure thing. Thank you. Hi everyone. I’m Scott Jones, VP of Product at a European computer vision AI company called Realeyes.

Realeyes was founded in 2007. I like to always joke that we’ve been waiting for this AI renaissance to catch up for almost 20 years. The co-founders originally coalesced around this opportunity of human understanding that led to developing proprietary models for measuring attention and emotion off of webcams and deploying that in the context of ad testing.

So conducting global market research on behalf of the world’s largest brands and agencies to essentially derisk their media spend. You can imagine for an audience like women with credit scores of 750 who have children and drive Subarus, what version of the ad on TikTok would be most performant versus YouTube.

I joined three years ago to lead a new platform business. The thesis of the platform is easy-to-use, plug-and-play capabilities such that you can now run our market-leading models in real time just about anywhere and solve problems that have never been possible before.

Shortly after I joined, we actually got into the identity category through our relationship with one of the world’s largest consumer app platforms. We’d already been helping them build avatars. They put out an RFI for a face verification model. Q1 of ’23, we threw our hat in the ring and we ended up winning their competition.

We then doubled down on that, really wondering what other problems we could solve in the identity space. We saw a really compelling opportunity in this white space between solutions that don’t really work like CAPTCHAs, device and network fingerprinting, SMS and email authentication, and heavyweight ID verification.

We found that there’s really nothing in between that works. So that’s where we’re at now — a solution that helps to provide human verification anonymously in seconds to validate personhood, uniqueness, and demographics without ever having to reveal exactly who you are.

I’ve been in my sixteenth year of product strategy and innovation leadership. No plan to get into product management. The universe hooked me up. It’s the coolest career on earth. So happy to be here.

Katherine Man Introduction (HubSpot)

Katherine Man | 00:19:10–00:23:40
Of course. Hello everyone. Thank you so much for taking the time to join us today.

My name is Katherine Man. I’m a Group Product Manager at HubSpot. I’ve been in product for over 10 years now. Similar to Scott, I never had a plan to be in product, but I was sold on it because someone said to me, “Hey, do you not know what you want to do after college, and do you like wearing a lot of hats?” And I was like, “Yes, you have me sold.”

Ten years later, here I am fully passionate about this space. I started my career out in healthcare with Athenahealth. Next up, I was at TripAdvisor in the travel industry, and now I work at HubSpot.

HubSpot is a customer platform that helps small to medium-sized businesses grow by bringing all of your go-to-market teams together in one place — marketing, sales, service — creating a unified view of your customer so all of your teams are speaking the same language.

I’ve been here for about five years. I just celebrated my sabbatical and got to do a trip to Asia, which I was really fortunate to be able to do. This is a problem I’m personally very passionate about. My dad is a small business owner, so really excited to be here and talk about this topic.

Classic Tech vs AI Replacement

Kenny Kranseler | 00:23:40–00:24:45
So what we’re going to do is I’m basically going to lead a panel, and you can pretend there’s this virtual couch that everybody’s sitting on.

To break the ice, if you were to think about what is the one piece of classic technology that you absolutely cannot live without, and which piece of AI-powered technology do you think will replace it first?

Anybody can jump in.

Scott Jones | 00:24:45–00:27:55
I was nodding. You saw me.

I’m a professional musician. I’ve been playing drums for 30 years. Drums are about as classic a technology as you can get — tens of thousands of years old. There’s really nothing like acoustic drums for feel and expressiveness.

Electronic drums have come a long way, but I’ve always said I need my acoustics. That’s changing. There’s a company called Sunhouse using AI where you put a single sensor on a real acoustic drum and it subdivides it into zones and assigns different sounds. It’s insane.

You still get to hit real drums, but they can be silent, and the sound quality is unbelievable. I just can’t justify the budget to my wife yet.

Ashka Vakil | 00:27:55–00:31:30
For me, it’s digital door locks. I work from home, run in and out all day, kids coming home, housekeepers, deliveries. Getting up during meetings is disruptive.

But it’s very binary. If someone has the code, they can get in. And you know how nine-year-olds are — they’re not good at keeping secrets. I’m pretty sure all my kid’s friends know our door code.

What I see AI replacing is intent-based ambient access. Facial recognition plus conditions. If I’m carrying groceries, open the door. If I’m on a bike, open the garage. If I’m with someone unrecognized, require secondary authorization.

That’s really aligned with what we do at StrongDM. It’s not static access. It’s contextual.

Katherine Man | 00:31:30–00:34:50
I’m more on the practical side. When AI came out, we thought finally it would automate everything we don’t want to do and give us time for hobbies.

Instead, AI is writing poetry and we’re still doing the dishes.

I look forward to the day when truly functional home automation gives me time back — not the robots crashing into mirrors. But honestly, I’d probably just watch more reality TV.

I’m really into realtor shows right now. Selling New York, Owning Manhattan. Selling Sunset has too much drama.

Defining the 2026 User & AI Agents

Kenny Kranseler | 00:34:50–00:35:35
So let’s talk about the user of 2026. How are they different? What do they expect that’s different from today? How is AI reshaping who the “user” even is?

Ashka Vakil | 00:35:35–00:40:15
I think we’re going to see new entrants of users — AI agents. They’re going to multiply.

Humans will become supervisors to those agents. In the space I work in, we used to talk about human and non-human identities. Now it’s agentic identities.

We already see engineers directing agents to write code and supervising outputs. That’s the big shift.

In terms of expectations, friction has no place anymore. Engineers go to lunch and come back to completed work. Logging in, VPNs, tokens — all of that is going to change.

But that also means we need guardrails. The blast radius of AI agents is far greater than humans. So speed with seatbelts is how I think about it.

Scott Jones | 00:40:15–00:42:30
I loved what Ashka said. Think about a simple two-by-two: human versus bot, good versus bad.

You already see people onboard as good humans and then replace themselves with bots later. Now imagine good bots representing humans, bad bots pretending to be good humans, agents acting on behalf of people.

It’s incredibly dynamic, and if you don’t know how to detect it, you’re compromised.

Friction, Speed, and Guardrails

Katherine Man | 00:42:30–00:51:10
What I’ve noticed is a rise of a new role — the AI generalist.

At first, I worried AI would replace PMs. Instead, PMs are more important than ever. We still need to define customer problems and validate solutions.

What’s changed is that I don’t always need a designer or engineer to prototype. I can ship something end-to-end myself.

That’s powerful, but dangerous. LLMs are great at creativity, not accuracy. The bar for trust is higher than ever.

Discovery, Research & New Feedback Signals

Kenny Kranseler | 00:51:10–00:52:00
So how does this change discovery? How do we learn when feedback becomes implicit instead of explicit?

Ashka Vakil | 00:52:00–00:57:40
Traditionally, discovery was about optimizing workflows and reducing friction.

Now it’s about outcomes. Agents don’t need UIs. Discovery cycles are collapsing.

We can talk to customers and generate clickable prototypes live. Feedback is immediate.

But failures can be silent. You need observability. You need to know what your AI is doing at all times.

Scott Jones | 00:57:40–01:02:15
Stripe is a great example. They trained models on billions of transactions and unlocked fraud patterns that were previously invisible.

AI enables discovery of problems we didn’t even know existed.

Personalization vs Privacy vs Trust

Scott Jones | 01:02:15–01:10:20
This all comes down to value exchange.

I’m building systems where you can’t lie, cheat, or steal — but you also don’t have to reveal who you are.

Some users will trade privacy for value. Others won’t. Products need to respect both.

We’re already in a world where you can’t trust what you see. Deepfakes are here. Trust has to be foundational.

Ashka Vakil | 01:10:20–01:15:40
At the core, it’s trust.

Users need control. Agents need identities, scopes, audit trails.

We talk about keeping AI on a leash — policies, monitoring, traceability. Same security principles as humans, but harder.

Predictions & Controversial Takes for 2026

Katherine Man | 01:15:40–01:19:30
My hot take: AI is a solution, not a strategy.

Customers feel AI fatigue. Not everything needs AI.

We went from shipping lots of AI features to realizing quality matters more than quantity.

Solve customer problems first. AI second.

Scott Jones | 01:19:30–01:24:10
Will the AI economy have a reckoning like the dot-com bubble?

There’s massive capital moving around with unclear enterprise value.

Trust will be the differentiator when the shakeout happens.

Ashka Vakil | 01:24:10–01:30:05
My prediction: for every human identity, there will be 100 AI agents.

Engagement metrics will die. We’ll measure agent performance instead.

PMs will need new metrics — outcomes over usage.

What Changes Most by 2026?

Kenny Kranseler | 01:30:05–01:33:40
Poll results show most of you believe trust and outcomes will matter more than engagement.

Metrics, AI PM Skills, Prototyping Tools

Panel | 01:33:40–01:43:10
Discussion covers synthetic users, Lovable, Figma Make, AI research cycles, outcome-based metrics, and pricing challenges.

Key guidance: AI accelerates discovery, but governance and validation remain critical.

Closing Remarks & Final Takeaways

Kenny Kranseler | 01:43:10–01:45:00
Thank you to our panelists and everyone who joined.

AI changes tools, not fundamentals. Trust, outcomes, and customer focus still win.

Happy holidays, and thanks for being part of the Productside community.