Experienced guidance
Thirty years in engineering and product, most of it spent building and scaling teams like yours. You get pattern recognition on the decisions in front of you, not guesswork.
Post-PMF advisory CTO / CPO for founders
Scale Without Losing Your Company's DNA
After a round closes there's pressure to hire senior leaders fast. I'm the advisor at your side while you find and grow the right ones.
Meet the scaling obligations to your investors on your own terms.
Reaching product-market fit and scaling past it are different problems.
Your team built something real: the tech is proven and customers want it. Turning that into a repeatable organization is a different kind of work, built on hiring, product process and architecture decisions that have to compound. It's work most founding teams are doing for the first time.
The pressure is to hire senior leaders fast. But fast often means importing playbooks from the new exec's last company, at the expense of what made yours work.
I join as an ongoing advisor: a sounding board for you, and a source of judgment on the roadmap, the hires, and the org decisions ahead, for as long as it's useful, at whatever pace makes sense.
Why bring in an advisor
Momentum, not a search
A CTO/CPO search takes months and a six-figure bet on fit. An advisory relationship starts this week, so you keep moving now and make the permanent hire deliberately, when it's the right person rather than the urgent one.
Grow your own leaders
If there's an existing team member ready to grow into a leadership role, I can work with them with 1:1 coaching.
How I help
Ways we can work together
Advisory Retainer
Ongoing counsel for you as CEO: roadmap, hiring, architecture, and org decisions, on a regular cadence of calls. This is the core of how I work with most clients.
Leadership Coaching
Dedicated time with an existing team member you're growing into a product or engineering leadership role: deliberate, ongoing development, not just advice for you.
Deep-Dive Engagements
For a specific high-stakes moment, like an architecture bet, a fundraise, or an executive search, a short, focused sprint alongside the retainer.
Approach
How the relationship works
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01
Introductory call
We talk through your team, goals, roadmap and pain points, and see if this is the type of help you need for where you're headed.
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02
Settle into a cadence
A standing weekly slot on a simple monthly retainer. Between calls, I'm a message away when something comes up.
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03
Resize as you go
We revisit the arrangement each quarter: deeper for a big moment, lighter as you build out permanent leadership, done when you've outgrown it.
About
Mark Wilkerson
Founder & CEO SimpleHerd Co-Founder SpeakUp
Thirty years in engineering and product, twenty-five of them leadership. I specialize in helping engineering-led startups make the jump from product-market fit to scalable execution. The operational, technical, and product foundations that growth depends on are the ones I've built before, and now that experience goes to founders as an ongoing advisor.
Whether as a founder, executive, or leader, I've led teams across enterprise SaaS, B2B and B2C platforms, robotics, physical AI, large-scale social media, streaming video, AAA gaming, finance, education, and government.
I provide a sounding board and a source of judgment on the roadmap and the hires ahead. The goal is simple: help you scale with confidence, without prematurely adding an executive to headcount.
Contributing author: Hacking Exposed, 4th Edition and Special Ops: Host and Network Security for Microsoft, Unix, and Oracle.
Companies
Let's talk about your team
30 minutes, no pitch deck. We'll figure out if this is the right fit.