HEMANT GUPTA — UX & Interaction Designer
Product Design / Microsoft SharePoint / Jan 2022 – May 2026

4+ years of
platform-shaping
design.

From template authoring to AI-powered vertical solutions — a continuous arc of system-level thinking, cross-functional ownership, and measurable execution.

3 Product Eras
4+ Years
12+ Features Owned
IC role Tactical + Strategic
Jan 2022 - Jun 2023

Content Assembly

Era 1 established the 0→1 foundation in template-driven generation, conditional logic, and bulk workflow direction.

Jun 2023 - May 2025

Agreements in Word

Era 2 pivoted into Word-native lifecycle design with stronger IA, reusable systems, and cross-team delivery scale.

Jun 2025 - May 2026

SPAI Verticals

Era 3 scaled the platform into AI vertical solutions with system behaviors, forms maturity, and strategy-level alignment.

Business Impact

10K+ NDAs generated
$705M+ Partner incentive letters
800K+ Documents processed
10 / 15 Top customers engaged
01
First Era
Jan 2022 – Jun 2023

Content Assembly

Evolving a rigid template product into a dynamic, conditionally-driven authoring platform — while simultaneously shaping the transition toward Word-native and AI-first experiences.

1 Designer 2 PMs ~5 Engineers IC Designer — MVP release execution for customer zero
Conditional Logic & Research

I led end-to-end UX validation for conditional placeholder and field logic, the feature that unlocked dynamic document generation without multiple template variants. I authored UT enquiries and ran prototype walkthroughs directly with users to stress-test field behavior, then translated those insights into the contextual content assembly specification using conditional placeholders (Jul–Sept 2022). This work also fed into CY23 H1 planning, where I contributed to strategy and adoption direction for scaling the capability (Nov 2022).

Conditional logic and research thumbnail

Deep dive is yet to be added. To be discussed in 1:1 setup.

Bulk and Automated Document Generation

I co-drove the design and feature direction for bulk document generation, establishing UX patterns that helped non-technical users trigger document production at scale. This included co-driving the Dec 2022 spec design review, contributing to automated generation scope and direction in Nov 2022, and shaping discoverability through an end-to-end list-page workshop in Jan 2023.

Bulk and automated document generation thumbnail Take a deeper dive
Contract Express Teardown: The Strategic Foundation

Before defining Agreements' direction, I conducted a competitive analysis of Contract Express—a leading legal tech document generation platform. The teardown validated questionnaire-driven workflows and clarified a hard architecture constraint in our existing Content Assembly model: because the experience was invoked from SharePoint and rendered in a webpage iframe with a side panel, true in-canvas editing in that offering was not feasible. This insight drove the pivot to provide template creation and document generation directly in users' Word flow of work, shifting the platform trajectory to Agreements (Word-native).

Contract Express teardown study thumbnail Take a deeper dive

Challenge Trigger: Why Content Assembly Had to Pivot into Agreements in Word

Evidence window: Jan 2022 – Jun 2023

In this phase, I helped prove demand for dynamic generation, but we also faced compounding delivery constraints: fragmented authoring surfaces, low discoverability, limited lifecycle depth, and unclear monetization communication for customers. These challenges directed the product to pivot into a Word-native, premium contract workflow model.

Jul–Dec 2022 Conditional placeholders and bulk DocGen specs validated value, but exposed complexity and setup friction for broad business-user adoption.
Oct 2022 PAYG billing UX and entitlement threads surfaced monetization clarity as a product requirement, not just a pricing-side task.
Mar–Jun 2023 Research and Word-native direction work converged on reducing context switching and moving contract workflows into the primary authoring surface.

Product constraint

Users had to jump between Word and web surfaces, templates remained power-user heavy, and discoverability was weak in list and entry-point flows, creating friction for non-technical adoption.

Business and monetization

Leadership needed a differentiated SharePoint Premium offering, while monetization work (PAYG and entitlement UX) made packaging clarity central to customer adoption conversations.

LT platform strategy

M365 and Word were shifting to AI-first authoring; I aligned with the team on a Word-native model because Content Assembly's SharePoint-invoked iframe + side-panel architecture could not provide true in-canvas editing for legal workflows.

Execution signal

Conditional logic, bulk generation, and research evidence proved demand for dynamic workflows, but also exposed lifecycle gaps, driving the move to Agreements in Word where review, amendment, and governance could be productized end-to-end.

02
Second Era
Jun 2023 – May 2025

Agreements in Word

Reframing contract creation from isolated authoring into a governed, Word-native lifecycle — with co-authored PM specs, amendment modeling, and AI-connected workflows as key outputs.

3 Designers 3 PMs ~11 Engineers IC Designer — influencing Word-native pivot; ramping up new members & mentoring peers
Agreements in Word — Walkthrough Demo In house demo video created with the team on what the Agreements in Word experiences like.
Agreements Ribbon IA — Word-Native Surface Design

I led the end-to-end information architecture for Agreements inside the Word ribbon, from early concept exploration through cross-team alignment with Word’s design partner team. Across multi-month reviews and workshops (Jan 2024 through Dec 2024), I explored three IA models, organized the core concept review, produced context-setting walkthroughs, co-drove tab icon workshops, and owned content-controls design; this work resolved the Backstage-versus-tab tension by formalizing a dedicated Agreements tab with licensing-driven visibility and consistent behavior across Win32, Web, and Mac.

Ribbon IA and Word partner collaboration thumbnail

Deep dive is yet to be added. To be discussed in 1:1 setup.

Component Library Foundation, E2E Template Creation, and eSignature Flows

I established the CA component library foundation and used it to create a consistency layer for the Agreements in Word era, enabling faster and more coherent delivery across designers and squads. In parallel, I independently drove the end-to-end Template Creation user journey through recurring experience reviews, carrying the flow from setup details to advanced capabilities such as conditional sections, richer template metadata, and integrated eSignature workflow paths. This was not a simple migration of Content Assembly UX into Word; it was a capability expansion that modernized authoring for production legal workflows while preserving learnability.

I also ramped up two new designers into high-impact ownership areas: one on Document Generation + Approval workflow and another on Manage Snippets. The operating model was deliberate: reusable component primitives, clear journey architecture, and review rituals that let multiple designers ship with one quality bar.

Design system and template creation journey thumbnail Take a deeper dive
Discovery, Backstage Integration and In-app learning videos

I led proactive design proposals that shaped how Agreements experiences are discovered and how AI capabilities are introduced to users, bringing design upstream into strategy rather than reacting downstream. I authored the Backstage discovery proposal, the Agreements In-app learning videos & help resources. For this I drove partnerships with Word team and did storyboarding with in house Motion designer for learning videos.

Design proposals thumbnail

Deep dive is yet to be added. To be discussed in 1:1 setup.

Challenge Trigger: Why Agreements in Word Had to Pivot into SharePoint AI Verticals

Evidence window: Jun 2023 – May 2025

In Agreements in Word, I helped establish a strong contract core, but the next challenge was scale: one solution line could not absorb cross-domain demand, AI expectations, and platform reuse goals simultaneously. Those pressures directed us to pivot into SharePoint AI Verticals.

2024 H1 Word-native lifecycle and DocGen Forms architecture stabilized, proving execution feasibility but also revealing reuse opportunities beyond contract-only scenarios.
2024 H2 AI roadmap, Copilot strategy, and platform threads shifted focus from feature completion to reusable intelligence and automation building blocks.
2025 Q1–Q2 Customer validation, performance, and scale discussions pushed operating decisions toward platformization, customer-first sequencing, and multi-vertical delivery.

Product maturity gap

Core contract workflows matured, yet backlog pressure shifted to reusable systems like conditional logic, form intelligence, and orchestration patterns that could serve multiple vertical scenarios beyond Agreements alone.

Business scale objective

The next growth step required expanding from a single contract solution into legal, HR, and procurement outcomes, improving TAM and reducing dependency on one workflow category.

LT strategy and AI

Copilot and AI roadmap work reframed the product direction around vertical intelligence, automation, and reusable platform components, with platform-vs-bespoke sequencing becoming a leadership-level decision thread.

Operating model shift

Cross-team execution required customer-first validation, reliability, and shared building blocks; this drove the SPAI pivot where DocGen Forms and conditional visibility became foundational capabilities for all vertical solutions.

03
Present Era
Jun 2025 – May 2026

SharePoint AI Verticals

Translating the forms and template platform into reusable, AI-native vertical solutions — with conditional logic as a platform anchor, and a sustained presence in strategic leadership alignment.

3 Designers 2.5 PMs ~14 Engineers IC Designer — strategic cross-functional alignment through ambiguous, fast-pivoting phase
SPAI Verticals — Vision Demo Since it is a vision demo, I cannot disclose the details due to NDA.
Conditional Visibility Logic — Design Owner

I led end-to-end UX direction for conditional visibility in DocGen Forms, treating it as a platform language rather than a single feature so legal, HR, and procurement scenarios could scale consistently. From Feb through May 2026, I owned rule-builder and show/hide semantics, authored the conditional visibility technical model, led wall reviews and Figma ERs, and contributed to adjacent autofill plus pagination and sectioning behaviors where visibility rules intersected implementation detail.

System-level design thumbnail Take a deeper dive
DocGen Forms — MVP through GA and V2

I contributed across the full DocGen Forms maturity arc from Sep 2025 to May 2026, spanning early platform evolution, GA readiness, and V2 alignment. The work included creation flow, navigation, AI field-detection UX, and end-to-end review support through Figma ER walkthroughs, with tracked attribution and a consistent focus on keeping Forms positioned as the foundational layer for AI vertical scenarios across the SPAI surface.

Platform execution thumbnail Take a deeper dive
Vertical Platformization and Leadership Cadence

I consistently participated in SP AI Leads syncs from Mar through May 2026, contributing to strategic decisions on bespoke-versus-platform sequencing, customer-first validation, and vertical architecture across legal, HR, and procurement. This leadership cadence built on my earlier contributions to AI vertical framing and solutions vocabulary (Jul–Oct 2025) and continued through HR workflow alignment work (Nov 2025–Mar 2026), with sustained cross-functional engagement across meetings, Teams threads, and email channels.

Strategy and alignment thumbnail

Deep dive is yet to be added. To be discussed in 1:1 setup.

What My Work Says
About Me.

Systems Thinking

  • I defined reusable interaction models for conditional logic across three product generations.
  • I shaped platform framing over isolated features throughout the SPAI arc
  • I connected UX semantics to implementation constraints and PM spec language.

Design Leadership

  • I co-authored three PM specs with direct implementation influence.
  • I proactively proposed discovery and AI onboarding designs ahead of roadmap.
  • I led wall reviews and Figma ERs for platform-defining capabilities

Cross-Functional Influence

  • I sustained collaboration with PM, engineering, and research across IDC, Dublin, and Redmond.
  • I participated in recurring leadership syncs at strategic decision altitude.
  • I reduced downstream rework by embedding design intent into specs early.

Execution Depth

  • I owned outcomes end-to-end from research validation through GA readiness reviews.
  • I maintained contribution across framing, iteration, and delivery checkpoints.
  • I surfaced blockers and unblocked teams across high-dependency threads.
Thanks for your time
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