I'm currently CPO at Siteimprove, deploying an AI-native product operating system that takes teams from raw customer signals to tested prototypes in under a day. I also coach first-time heads of product and founders on strategy, pricing, and executive leadership. The advice I give is grounded in what I'm building right now.
Active operator
I'm CPO at Siteimprove, navigating AI transformation, pricing decisions, and org design challenges at scale right now. I coach from current experience, not a retrospective.
B2B SaaS, every stage
My entire career is B2B SaaS. PLG startups, growth-stage companies, and enterprise scale. SendGrid through IPO, Twilio post-acquisition, Contentful, Siteimprove. The exact context your challenges live in.
Deep pricing expertise
I built pricing strategy at SendGrid from zero and drove $20M+ in revenue impact. I'm currently leading a pricing and packaging revamp at Siteimprove. This is lived expertise.
"Most first-time product leaders are promoted for execution and then expected to operate strategically. Nobody teaches them how."
The gap between strong PM and great product leader isn't skill. It's perspective, pattern recognition, and having someone honest in your corner who's navigated the same challenges at scale.
Moving from shipping features to shaping business outcomes.
Operating credibly at the CEO, board, and ELT level.
Turning product decisions into revenue architecture.
Moving from AI hype to real agentic product strategy.
Individual coaching for product leaders. Transformation advisory for product organizations. Different engagements, same approach: direct, evidence-based, grounded in what is working today.
Track 3: Advisory
For CPOs and VPs of Product at B2B SaaS companies who need to transform how their product teams discover, validate, and ship. A structured 6-week pilot that deploys an end-to-end AI-native system across your product org. Not a workshop. A working system.
Every engagement is different. Most of my clients are scaling B2B SaaS companies and dealing with a mix of these challenges at the same time. We go where the work is most pressing.
Defining a compelling North Star, building a narrative that lands with investors and leadership, and translating vision into a roadmap that drives real outcomes.
Pricing is the most underleveraged lever in product. We work through monetization architecture, tier design, and how to frame pricing changes internally and externally.
Designing and deploying an end-to-end AI product operating system: signal synthesis, living opportunity briefs, PM-generated prototypes, and research previews. I'm building this in my current role right now, not advising from theory.
Team structure, PM career ladders, operating models, and how to build a product organization that can scale from scrappy to strategic. Includes discovery practices, hiring, and culture change.
Building shared language between product, sales, and marketing around positioning, ICP, and how product decisions drive expansion revenue.
Operating at the ELT level, communicating with boards, managing CEO expectations, and developing the executive presence that earns trust across the organization.
I've been there. I built the product org at Red Canary from scratch. 20+ people hired in under a year, two new products shipped to $2M+ ARR.
I built SendGrid's pricing strategy from zero and drove $20M+ in revenue through pricing alone. I'm leading a pricing revamp at Siteimprove right now.
In my current role as CPO, I'm building an AI-native product operating system that takes teams from raw customer signals to a tested prototype in under a day. I can help you build something real.
I'm currently CPO at Siteimprove, on the Executive Leadership Team, where I launched a new product strategy and built the AI-native product operating system I now offer as an advisory practice. Before that, I was VP of Product and Interim CPO at Contentful for three years, and VP of Product at Red Canary where I built their first product function from scratch.
Earlier, I led product at Twilio after the SendGrid acquisition, and spent three years at SendGrid through their IPO in 2017 and Twilio's $3B acquisition. I've built products at every stage of growth, and I've lived the VP to CPO transition more than once.
I keep my client list small on purpose. Every engagement gets real attention and a fresh perspective on your specific situation.
🎤 Frequent speaker at corporate product management events, covering customer-first discovery, zero-to-one strategy, de-risking innovation, and AI-first product transformation.
"Kalvin has a rare ability to cut through the noise. In our first session, he reframed a problem I'd been stuck on for months. His combination of strategic clarity and operational experience is exactly what I needed stepping into my first VP role."
"As a founder, I needed someone who could think about pricing as a product problem, not just a finance exercise. Kalvin helped us completely restructure our packaging strategy. The impact was immediate."
"What sets Kalvin apart is that he's doing the work right now. He's not giving advice from 10 years ago. He's navigating the same AI transformation questions I am, just at a larger scale. That context is invaluable."
Built and measured in production. These are real outputs from a real product org running the full system.
Down from 15 to 20 hours per cycle. AI-synthesized intelligence briefs replace manual reviews of product analytics, support tickets, and sales calls.
"This blows out of the water the brief my PM spent 3 months creating. Richer evidence, clearer framing, prototype-ready output." — VP of Product, enterprise B2B SaaS
From raw customer data to a clickable, customer-tested prototype. Not a mockup. A working prototype validated with real users before engineering invests.
Signal synthesis, vision hypothesis, opportunity brief, and prototype concepts. Used daily across the product org. Each skill is customized to the company's strategy and tool stack.
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Follow on LinkedInI work with a small number of clients at a time. Start with a 30-minute intro call. No pitch, just a real conversation about where you are and where you want to go.
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