Spryker Systems

BigCommerce

eBay Inc.

PayPal

Elena Leonova

Founder & CPO, OneRank.io,  ex-CPO @ Spryker, VP of Product @ BigCommerce

Cohort 4

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At senior levels, decisions don’t move forward because they’re correct.They move forward because they’re&nbsp;trusted.Many PMs don’t realize they’ve lost influence until decisions start happening without them. This session helps you see why - and what executive judgment actually looks like in practice.

Why Executive Decisions Move Forward Without You


If you want to move from “managing features” to&nbsp;leading the business, you need a simple, repeatable way to explain&nbsp;why your roadmap matters in terms executives care about.The&nbsp;ROI Roadmap Canvas™&nbsp;is the exact framework I’ve used as a Product Executive to secure budgets, justify strategic decisions, and communicate product priorities to CEOs, boards, and cross-functional leaders.You’ll learn how to:<ul><li>Translate&nbsp;any&nbsp;feature into business outcomes</li><li>Tie work to ARR, GRR, NRR, CAC, and payback</li><li>Prioritize based on impact, not stakeholder pressure and mor</li></ul>

The ROI Roadmap Canvas™: The Framework Product Leaders Use to Prioritize Like Executives


Most PMs look at roadmaps.Executives look at&nbsp;business drivers&nbsp;and&nbsp;KPIs.This cheat sheet bridges that gap.It gives you a crystal-clear view of how initiatives map to the four business levers every CEO and CFO care about — and the KPIs that prove impact: ARR, GRR, NRR, CAC Payback, Cost-to-Serve, and more.Use this guide to:<ul><li>Understand how executives evaluate product decisions</li><li>Map your roadmap directly to revenue, cost, risk, and strategic leverage</li><li>Identify which KPI is signaling a problem — and which lever to pull</li></ul>

The 4 Drivers → KPI Mapping Cheat Sheet: How Product Executives Think About the Business


You will learn how to make and recommend strategic decisions grounded in business reality -  not feature logic.

ex-Product Exec @Spryker, Commerce, eBay

From PM to Strategic Product Leader: Make Decisions Leadership Trusts

Senior Data Product Manager

Head of Product (Sr. Group Product Manager)

Product Manager

Product Coach

Senior Technical Product Owner

Senior Product Manager

At senior levels, product leadership stops being about having the best answers. It becomes about being trusted with decisions. You’re expected to connect product bets to revenue, cost, and risk — and defend those decisions under pressure.But most product leaders were never taught how those decisions are actually made.So decisions move forward without you. Not because you lack context. But because others are framing the business problem more clearly. They connect strategy to financial reality, risk, and trade-offs. And their judgment lands.This course exists to change that. This is a 6-week, high-touch cohort where your judgment is tested the way it's tested in leadership rooms.You will practice making strategic decisions through real scenarios:• diagnosing business pressure • translating KPIs into strategic bets • navigating financial tradeoffs • defending strategic decisionsYou won’t just learn frameworks. You will apply them live and receive direct feedback on whether your reasoning holds up.It’s judgment that holds when the stakes are real — and the room is deciding whether to trust you. If you want to move from executing strategy to shaping it, this is where that shift happens

Think like a VP before you become one. Ground Product Strategy in business.

Understand the business before building the strategy

Use financial metrics to guide strategic decisions

Build a credible, business-backed product strategy

Present strategy to executives and boards

Partner effectively with Sales, Marketing & Customer Success

Lead with strategic judgment & influence without authority

You already operate as a Senior or Principal PM or Product Lead. You don’t need help shipping, running discovery, or managing teams

Strong Product Execution Fundamentals

You’re used to making calls with partial information, competing metrics, and real tradeoffs. You understand the importance of judgment

Comfort Making Decisions with Imperfect Data

Your judgment is - or soon will be - evaluated by executives, boards, or clients. You’re responsible for explaining why a decision is right

Accountability for Strategic Decisions

Senior &amp; Principal PMs who already deliver at a high level and want to be trusted with larger, riskier decisions - not just execution

Group PMs, Directors, and above who own strategy, make real tradeoffs, and defend decisions under executive scrutiny

Product consultants, coaches, and advisors who want to bring executive-level judgment to their client work and recommendations

Your strategy is sound. The room still didn't get it. This workshop fixes that.

You can build a sound strategy and still lose the room.Most product leaders aren't unclear. They're at the wrong altitude. They lead with user workflows when the board wants market opportunity. They walk in with 30 slides when the CEO has 5 minutes. They explain why the work matters when executives are deciding how much it's worth.The cost isn't a bad meeting. It's a worse career trajectory. Decisions move forward without you. Headcount goes elsewhere. Roadmaps get rewritten by people closer to the money.This workshop fixes one thing: how you communicate product strategy when the room is deciding whether to fund it, defend it, or push it back to next quarter. Four hours, hands-on, with live coaching from Elena. You leave with a rewritten exec update for a real situation in your own work — pressure-tested by your peers and critiqued live.This is not communication theory. It is what gets the yes.

Translate product strategy into the language executives decide in — capital allocation, risk, market opportunity. Land the yes.

Diagnose the altitude of your last exec update

Architect every update around the three executive questions

Pre-wire your decision room before the meeting starts

Pitch your real proposal under live pressure 

This is hands-on. Bring an actual situation from your work — board deck, exec update, strategy ask. No fictional case studies.

A real exec update or stuck proposal you need to nail. 

No prior coursework required, but you should already be operating in rooms where executives evaluate your judgment. This is not a foundation

Senior PM level or above. 

Block the calendar. The practice + critique element only happens live. Showing up at minute 30 will cost you the value.

Four hours uninterrupted. 

Senior &amp; Principal PMs whose strategic proposals keep getting translated, redirected, or politely ignored by the exec team.

Group PMs, Directors, VPs of Product who've lost — or nearly lost — a critical decision because the room didn't land as expected.

Product consultants and advisors who coach senior PMs through executive presentations and want a sharper toolkit for the altitude shift.

The Three Questions Your Execs & Board Actually Cares About

Boards care about market opportunity, capital efficiency, and risk profile. Everything else competes for slide budget.

Lead your update with the right three questions

Identify the slides that drain execs & board attention from your strategic ask. Rewrite a 30-slide deck into a 3-slide o

Cut the 27 slides your execs and board doesn't need

Cutting slides is the easy part. Defending the cut to your CEO is the hard part. Learn the conversation that closes it.

Defend the update scope to your CEO before the meeting

Founder-CEO Trusts Gut Over Your Data: The Translation Move

Identify which founder pattern you're working with - and which translation move actually lands for each one.

iagnose three founder-CEO archetypes

Walk through your specific founder relationship using the same diagnostic that works in the room - not the framework.

Apply the translation move to your actual scenario

Influence with a founder-CEO is a routine, not a presentation. Map the cadence and the small wins that compound.

Build a 90-day influence routine, not a one-shot pitch

Stop Letting Loud Signals Hijack Your Roadmap

Most teams react to the loudest signal - sales requests, bad NPS, support spikes. Learn which signals earn the change.

Diagnose why your roadmap keeps shifting without moving

Decide upfront what signal would force a roadmap change. Without it, every signal gets rationalized away.

Pre-commit the threshold that triggers a change

One loud customer is not three KPI shifts. Learn how to weight signals so the wrong one doesn't hijack your strategy

Weight aggregated vs one-off signals correctly

The Altitude Gap: Why Executives Talk Past Your Update

Score your last update against three altitude markers: capital signal, risk signal, decision-rights signal.

Learn the PM-default phrases that signal you're operating at the wrong altitude - and what executives hear instead.

Spot the language patterns that cost the room

Rewrite an actual exec update at a live altitude rewrite. Learn how to apply the same diagnosis to your updates.

Rewrite one exec update at executive altitude

The 6 Questions That Separate Strategy from a Funded Wish

Run your top initiative through the 6 questions executives actually ask. Find which answers expose weak strategy.

Stress-test any strategic bet in 60 minutes

Most roadmaps are capital allocation decisions pretending to be prioritization. Learn how to spot the difference fast.

Diagnose roadmaps disguised as prioritization

Apply the 6 questions across your full roadmap to identify bets that don't change business economics meaningfully.

Build a portfolio that survives executive scrutiny

The Number Your CFO Already Knows That Will Kill The Roadmap

Map the numbers your CFO tracks against your top 3 initiatives. Find the one that will surface in the board.

Identify the financial number that breaks your roadmap

Walk out with a structured diagnostic that surfaces the financial vulnerabilities in your roadmap before the execs do

Build a one-page executive team diagnostic for your roadmap

Reframe your top 3 initiatives in terms of capital allocation, exit math, and risk - the only frame your CFO speaks.

Learn directly from Elena Leonova

Elena Leonova

About Elena

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