Coach to Product Leaders | ex-Facebook, Instagram, Nokia, eBay, Skype, Microsoft

I spent 27 years optimizing products for billions of users at Meta, Microsoft, Skype, and Nokia. We had rigorous frameworks for shipping code, managing KPIs, and scaling tech.

We had few frameworks for managing the human operating system driving it all.

I watched brilliant leaders suffocate under the "Asphalt."

In my book, I define the Asphalt as the "clearer path to lesser goals." It is the artificial layer of safety, optics, and "good enough" that society paves over our true potential. Most leaders don’t lack skill; they lack alignment. They are trapped beneath the weight of expectation, shipping the org chart instead of the product.

I codified the process of breaking through into a structured system: The S.E.P.A.R.A.T.E. Framework™.

This is a proprietary tool I created to help leaders break through the pavement of convention. Today, I serve as an Executive Coach and Consultant for those ready to stop managing friction and start engineering flow. I use this framework to debug performance with the rigor we apply to code. No fluff, just root-cause analysis and architectural repair.

HOW I PARTNER WITH CLIENTS:

1. LEADERSHIP TEAMS: The "Alignment Diagnostic" & Intervention. We identify the 5 signs of "Destructive Discomfort" that are silently draining your capacity and install the protocols to fix them.

2. LEADERS & HIGH-PERFORMERS: 1:1 Alignment Coaching I partner with Execs, Founders, and individuals to audit their professional lives. We identify where you are buried under the "Asphalt" (Safety/Convention) and build the strategy to break through to your "Steeper Path" (Growth/Purpose).

3. THE MANUAL: Breaking Asphalt My book, Breaking Asphalt: Choosing the Steeper Path to Greater Goals, is the tactical documentation of this system. (Available globally).

4. THE STORIES: The Steeper Path. I host The Steeper Path podcast and newsletter, exploring the mechanics of alignment with other industry leaders.

READY TO UPGRADE YOUR OPERATING SYSTEM?

I work comfortably with a small roster of high-impact clients. If you are ready to break through, let’s have a brief conversation to see if we are a fit for each other.

Book an Intro Call: https://app.paperbell.com/checkout/packages/96280

Newsletter: https://lennpryor.kit.com/75a08a3fcf

Podcast: https://thesteeperpath.buzzsprout.com/

Lenn Pryor

Manager of Customer Success @ Lokalise | Driving Customer Success, Revenue Growth

I’m a Technical Customer Success Manager with deep experience in B2B SaaS, specialising in API-first and data-heavy products. I work at the intersection of customers, product, and data, helping technical teams turn complex platforms into predictable, repeatable outcomes.

At Modash, I operate in a foundational role for the API business, owning the customer motion from onboarding through renewal. My focus has been on introducing structure where things were previously reactive: standardising onboarding and contracts, improving pre- to post-sales handoffs, building deal and renewal forecasting, and implementing usage-based health scoring so customer risk is assessed against real product usage rather than subjective sentiment.

I work closely with developers, product teams, and founders, supporting integrations, structuring data flows, and ensuring the API becomes a durable part of customers’ workflows. The work is less about firefighting and more about building systems that make outcomes predictable at scale.

Earlier in my career, I’ve helped scale post-Series B organisations and contributed to building customer success operations from the ground up, including CRM workflows, forecasting models, and enablement frameworks. Across roles, my bias is always toward repeatable process, clear ownership, and strong cross-functional alignment.

Outside of work:
🎣 Fishing keeps me grounded and creative
👨‍👧‍👦 Fatherhood keeps perspective sharp
🌍 Life in Italy has built adaptability
🥾 Hiking and travel fuel long-term thinking
🍇 Wine and winemaking reinforce patience and craft

Professionally, I’m interested in how data, automation, and human judgment combine to deliver great customer experiences. If you’re working on scaling customer success, API-driven products, or connecting CX with commercial outcomes, I’m always open to thoughtful conversations.

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