$180 / month
Start free, decide later
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I help technical managers, analytics leads, and high-performing ICs navigate the part of the job no one puts in the handbook: the space where logic meets messy, real-world business operations. Moving into strategic lead or PM roles isn’t just about bigger scopes — it’s about learning how decisions actually get made, what the business truly values (versus what it says it values), and which levers you can realistically pull to keep a product roadmap alive. It’s about figuring out how to translate an algorithmic model into an intuitive user workflow, how to run rapid experimental loops without breaking organizational trust, and how to shield your execution track from the churn of every new corporate “operating model refresh.”
I also help technical folks map out their trajectory—whether that's transitioning into product management, taking on a strategic program lead role, or deciding if traditional people management is actually the right move. Not everyone wants to trade technical depth and hands-on building for budget meetings and inbox maintenance. I’m honest about what each track costs, what it buys you, and how to make the leap.
I can also help firms sort out fact from fiction as they navigate their first wave of AI vendor pitches, cloud platform sales decks, and digital transformation slideware. Whether it’s deciding if you actually need a platform engineering team, whether your business is ready for GenAI tooling, or how to hire your first data scientist without falling for buzzword theater — I’ve lived through that transition and can help you avoid the usual expensive mistakes. I’m especially attuned to operationally grounded product and analytics work where margin, inventory, throughput, and staffing matter more than your latest cloud-native architecture diagram. I won’t quote HBR at you, and I don’t believe a product strategy workshop is going to fix your stock-to-sales ratio. I’ve spent years delivering pragmatic products in environments where data maturity is a slogan and transformation initiatives are a line item. If you’re trying to build something that actually works anyway — or deciding which track you want to run on next — let's compare notes.
You tell Zachary your goals. They see exactly what you want to work on before session one.
You meet within days. Zachary reviews your application and books your first session, usually within a day or two.
You leave with a plan. Concrete next steps and a weekly rhythm from your very first week.
Zachary Singer-Leavitt
Director, Data Science at CVS Health
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Book a free intro call with Zachary
Connect with Zachary in a quick call (usually 15-20 minutes)
One-off sessions with Zachary
One-off sessions are a great option if you're looking for specific advice on a certain topic.
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Whatever doesn't fit the mold: Get a full hour with a mentor to discuss your needs. Be it help with coding something, deciding on a …
What's included in the trial?
Every trial is a little different–here's what Zachary says about their trial:
Hello! I mentor data leaders and high-potential ICs on the uncomfortable truths of the job: how decisions actually get made, what the business truly values, and how to deliver operational value far from Silicon Valley hype. During the trial, we'll schedule a ~15 minute call. To ensure the best fit, please share your current goals and pain points beforehand. We'll use the call to confirm logistics and ensure I'm the right mentor to help you achieve and resolve them.