Tristan Douville

Context

Leadership proposed a new feature to help customers manage renewal terms within contract documents — a known pain point for users managing long-term agreements.

Problem

Initial designs aimed to model every possible renewal scenario across all document types. While comprehensive, this approach introduced significant technical complexity, a high cognitive load for end users, and a timeline that would delay a widely-requested feature.

Core tension: Deliver a complete solution vs. deliver a usable solution quickly.

There was also internal misalignment — leadership favoured the more robust approach.

My Role

• Analyzed session recordings and support tickets to understand real user behaviour
• Used LLMs to review OCR'd contract text and identify patterns in renewal terms
• Found that the majority of users had simple, repeatable renewal patterns
• Facilitated discussions with leadership to refocus on core user needs
• Managed stakeholder expectations during a decision conflict

Key Decisions

1. Reduce scope to match real usage
Prioritized a recurrence-based model covering the most common renewal scenarios. Avoided building for edge cases upfront.

2. Leverage known patterns
Drew from existing SaaS conventions and competitor solutions to reduce the user learning curve.

3. Position as an MVP
Framed the solution as a test of user demand, keeping the door open for expansion. This reduced resistance by aligning on iteration over perfection.

Execution

• Partnered with engineering to define a lean, flexible recurrence system
• Kept scope tightly aligned to core use cases
• Instrumented the feature with Mixpanel to measure adoption and usage patterns
• Led internal enablement and external rollout through documentation and customer education

Outcome

• Feature launched successfully and remains in active use
• Covered ~95% of customer use cases, validating the simplified approach
• Avoided significant engineering investment in low-frequency edge cases
• The "comprehensive" solution was deprioritized indefinitely, freeing capacity for higher-impact roadmap items

Context

The product team was increasingly pulled into customer support — fielding interruptions via Slack, email, and calls to help resolve tickets. Comprehensive documentation, PRDs, and BI tools existed but were underutilized by the Customer Success (CS) team.

Problem

Support staff relied on the product team for answers instead of self-serving through available resources, causing:

• Constant interruptions to product work and roadmap execution
• Slower response times due to dependency on PM availability
• Underutilization of existing documentation

Core tension: How do you enable support to independently access product knowledge without making the product team a bottleneck?

My Role

• Owned internal documentation strategy as part of the product team
• Interviewed CS team members to understand their real-time support workflows
• Identified that the issue wasn't lack of documentation — it was lack of accessibility and synthesis
• Explored solutions ranging from process improvements to tooling

Key Decisions

1. Validate non-technical solutions first
Improved internal documentation and ran a lunch & learn on effective self-serve questioning techniques (adapting PM-style user interviewing for support). Helpful, but did not reduce reliance on the product team.

2. Invest in a scalable system
Identified an opportunity to use AI to aggregate and synthesize internal knowledge. Proposed an internal "Product Concierge" to enable real-time, self-serve answers.

3. Prioritize trust and accuracy over breadth
Designed the system with strict guardrails: surfacing source references, indicating the age of information, and limiting responses when confidence was low.

Execution

• Defined requirements and architecture for a Slack-based AI assistant connected to internal documentation, PRDs, code repositories, and select BI queries
• Collaborated with developers to validate the approach and ensure feasibility
• Built and iterated on the solution, refining prompts and data connections
• Implemented tracking to monitor usage and response quality

Outcome

• "Product Concierge" is now actively used, handling hundreds of internal queries per month
• Reduced direct interruptions to the product team
• Improved speed and consistency of support responses
• Created a scalable knowledge system, reducing dependency on individual team members
• Established a foundation for future internal AI tooling

Context

A high-value client relied on email and spreadsheets for a critical financial workflow and experienced delays in their year-end reconciliation due to missing records. They came to our product and leadership team with a request to build a proper solution.

Problem

The client required a highly customized workflow our product didn't support. Key challenges included:

• A time-sensitive deadline tied to their fiscal year-end
• Conflicting requirements across multiple client departments
• One-off solution risk — potential roadmap diversion without clear reuse potential

Core tension: Solve a critical client problem quickly without introducing long-term product bloat.

My Role

• Led user interviews with client stakeholders to uncover root workflow issues
• Synthesized findings into clear product opportunities for leadership
• Owned the PRD and solution design, including a functional prototype
• Liaised with Customer Success and Engineering to ensure alignment
• Acted as the bridge between client needs, business goals, and technical feasibility

Key Decisions

1. Build vs. defer

• Option A: Defer to protect the roadmap
• Option B: Build a one-off solution
• Option C (chosen): Build an MVP with a scalable architecture

2. MVP scope definition
Prioritized only the core workflow blockers for year-end readiness. Deferred edge cases to post-launch iterations.

3. Platform investment
Designed the solution to support configurable workflows (fields, statuses, naming), with clear potential for reuse across other clients.

Execution

• Aligned internal stakeholders on scope vs. timeline tradeoffs
• Collaborated with engineering to define a flexible technical design under time constraints
• Presented a client-facing proposal including problem framing, a prototype walkthrough, a delivery plan, and a pricing and support model

Outcome

• Client accepted the proposal, increasing spend by 20% YoY
• Delivered on time for fiscal year-end
• Established a foundation for configurable workflows, enabling reuse across other clients
• Project success generated an internal referral, expanding into additional opportunities within the client's organization