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0 → 1 Sales Enablement AI Coaching Platform Design

Conversational Coaching

An AI-powered sales enablement platform that analyzes seller-customer interactions to deliver automated, real-time coaching — replacing a third-party tool with a superior internal alternative.

This work is under NDA. Visuals and specific metrics are redacted. The narrative focuses on design thinking, strategic approach, and impact at a structural level.

What it is

An AI-powered sales enablement platform that analyzes seller-customer interactions to provide automated, real-time coaching. I defined the end-to-end UX for the 0 → 1 experience, positioning it as a superior internal alternative to the third-party competitor already in use.

The problem

Fragmented coaching landscape

Coaching frameworks varied by team, market, and region. Sales mastery programs offered pre-pitch simulations, but there was no unified, data-driven system for post-interaction feedback at scale.

A compromised external tool

The existing third-party solution required heavy redaction of critical context before conversations could be analyzed. No revenue numbers, no customer names, no prior activity — each interaction was stripped of the nuance that makes coaching meaningful. Every pitch was treated as isolated, unable to account for advertiser reception, relationship history, or evolving account dynamics.

No separation of signal from noise

The external tool couldn’t distinguish seller behaviors from external factors that influenced outcomes — macroeconomic shifts, advertisers reallocating budgets across channels, or changes in marketing strategy. Coaching feedback lacked the context to be truly actionable.

What I did

Scalable framework

Designed a modular UI system — media players, transcript viewers, and annotation layers — that now serves as the standard for all conversational applications within the Ads CRM platform.

Strategic socialization

Led workshops with regional managers and sellers to validate coaching flows, ensuring the tool addressed high-friction pain points in the actual sales cycle rather than assumed ones.

Cross-functional alignment

Navigated conflicting requirements between Sales Ops and Engineering to land on a version that prioritized transcript accuracy and immediately actionable feedback — the two dimensions that mattered most to sellers.

Designing for trust

Sellers carried an inherent fear that this tool would become a surveillance instrument. I designed transparency into every layer: clear visibility into what data is shared with managers, how scorecards reflect performance, and where the boundaries of coaching vs. evaluation live. The tool had to feel supportive, not punitive.

Why it was hard

Trust vs. accountability

The core tension was designing a tool that felt genuinely supportive for sellers while simultaneously delivering the accountability and scalable technical framework that leadership and adjacent teams (Support, Marketing) needed to justify long-term investment.

Replacing an entrenched tool

The third-party solution, despite its limitations, had organizational inertia. Sellers and managers had adapted their workflows around it. Displacement required not just feature parity but a demonstrably better experience on the dimensions users cared about most.

Impact

79% CSAT
Outperformed the primary external competitor, with 89% transcript quality rating
$XXXM
Annual TAM captured, with $XM in OpEx savings by replacing the third-party tool
Efficiency
Projected to save XX headcount hours through automated feedback loops for managers
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Perpetually in a state of beginner's mind.