# Lindsie Canton & Neil Power -- Problem Solving Round
**Date:** 2026-03-05, 12:00-1:30 PM PST
**Format:** Live case exercise + operational discussion, conversational
**Vibe:** Very conversational, warm, free-flowing. Both were lovely. More forgiving feel than Riley's structured approach. Neil pulled up artifacts and screen-shared. Both talked a lot -- good sign of engagement, not a checklist.

## Case 1: Competing Initiatives (Priority Conflict)

Two major initiatives competing for capacity:

- **Initiative A:** Engineering work, sounded like refactoring. Foundational improvements to enable operational efficiency and accelerate future features. No clear metrics or measurable outcomes -- only operational efficiency improvement.
- **Initiative B:** Highly requested, highly valued feature with clear measurable revenue uplift in dollars. Required a complex third-party integration.

### Andrea's Clarifying Questions
- Product-market fit status? Good PMF, core product working well for most users.
- Company goals? Typical fintech: TPV and ARR. (Lindsie's answer)
- Core persona? Yes, clear persona forming majority of customer base.
- Scope clarity? Both initiatives had clear requirements and outcomes.

### Andrea's Recommendation: Initiative B
**Reasoning:**
- At a stable point with good PMF, it's the right time to push for growth
- Initiative B has clear, measurable revenue uplift vs. Initiative A with no metrics
- Market timing matters -- revenue opportunities have windows, tech debt doesn't. Seasonality in selling, fiscal year closures, renewal cycles create urgency for B that doesn't exist for A.

**Caveats raised:**
1. Third-party integration is scoped as complex, likely to be even more complex. Is it critical path or deferrable?
2. Hedged on tech debt: "I always support removing tech debt, but it lives forever and is always how much to manage and how urgent it is."

### Neil's Pushback
- Used analogy of tech debt as a financial loan -- some debt is healthy leverage
- Andrea held position while acknowledging the analogy
- Used the Ting beta program provisioning story as counter-example: sometimes tech debt is proven undeniable by real results (provisioning lag with real customers showed old microservice was incompatible with new equipment, forced a complete rebuild)

### Follow-up: Communication & Tactical Trade-offs
**How to present to Jonathan and teams:**
- Different fidelity for different audiences
- Concise synthesized conclusions for Jonathan with supporting arguments available for drill-down
- Visual-first approach -- high-level top-down view most beneficial
- Central location for all information at different levels of detail
- Philosophy: "People don't read, but information should be available and accessible when they choose to"
- Clear ownership so Andrea isn't the sole point person for all questions

## Case 2: Internal Tooling & Cross-Team Coordination

Neil and Lindsie walked through the current tech stack and tooling:

**Tools mentioned:**
- Jira (project per engineering team, top-down admin rules for statuses)
- Intercom (CX tickets flowing into Jira)
- Notion (doc store)
- Figma / FigJam (design)
- Slack
- Miro (cross-functional collaboration)
- Claude Code (recently adopted)
- Cursor (considering)
- Reforge, FullStory, Gong
- Salesforce (CRM, source of truth for account data)
- Vitally (customer success)

**Recent win:** Just established a common dashboard/view for all teams to see shared information.

### Neil's Specific Problem: Intercom/Jira Integration
CX tickets flowing into Jira, engineering triaging many back to CX as "not a software issue -- this is usability / expected behavior." Lots of wasted eng time on triage.

**Andrea's response:**
- "I was the human interface" -- as a PM, she bridged CX and engineering directly
- Without shared cross-functional dashboards, relied on one-on-ones with team leaders to get the pulse beyond reports
- Acknowledged this is time-consuming but necessary until shared language and swim lane clarity exist
- Practical suggestion: get CX to pre-filter, tag, and categorize tickets before routing to engineering. Triage at the source reduces downstream noise.
- As a product person, had to know the voice of the customer -- what's urgent vs. not, important vs. not. Human judgment is the critical interface.

### Neil's follow-up: How would Andrea use Jira?
- Two-week sprint cycles
- Standard scrum: backlog grooming, prioritization, standups
- Measure progress and directionality through sprint cycles
- Resource allocation awareness (team availability, vacation)
- Sit in retros for directionality signal -- are we building the right thing?
- Watch for tickets carried across multiple sprints or scope growth as indicators of misalignment
- Manage scope creep iteratively through planning cycles

## Case 3: Change Management (Lindsie's Question)

**Question:** Example of pushing forward with a change that created pain for a specific team.

**Andrea's answer:** GTM rollout at Ting -- splitting markets and adding a brand new system for CX operations. Added significant workload: new system to learn, multiple customer journeys to route.

**How she managed it:**
- Worked with teams to reduce pain wherever possible
- Tackled easier markets first, batched for manageability
- Showed tangible value at the end of the rollout -- demonstrated what the hard work achieved
- "The pain came with an expectation that there's something better on the other side, and I was able to demonstrate that tangibly"
- For operations people, this is a clear win: harder work with something gained at the end

## Case 4: Change Management Philosophy (Lindsie's follow-up)

**Question:** How would you introduce change management for new workflows and processes?

**Andrea's philosophy:**
- "Change hearts before minds" -- can't reason with someone who's adversarial
- Create psychological safety first -- let people share fears and concerns
- Some fears are legitimate and need to be actioned on; some are unwarranted
- Establish rapport and relationships before starting any change
- Culture, community, and belonging (Lalamove example) -- when people identify with the greater goals, they're more resilient when methods change but goals stay the same
- Distinction between perceived responsibility vs actual responsibility -- lines between teams are often muddy, need to be clarified

**Andrea noted:** The framing in the debrief was better than live delivery, but believes the core message still landed well. Felt both interviewers were quietly impressed with this answer.

## Overall Assessment

**Strongest moments:**
- "Change hearts before minds" -- a philosophy, not a tactic. Memorable.
- Perceived vs actual responsibility distinction -- sharp operational insight
- Provisioning story as proof that tech debt can be undeniable
- Market timing argument for Initiative B prioritization (new tool, not in practice sessions)
- Pre-filtering CX tickets at the source -- practical, unglamorous, exactly what the role does

**Patterns across all rounds today:**
- Conversational format suits Andrea well -- more relaxed than Riley's structured approach
- Clarifying questions are becoming consistent (PMF, company goals, scope clarity)
- Strongest when drawing from real experience (Lalamove, Ting beta, GTM rollout)
- Change management / culture answers are a differentiator
- Weaker on specific tooling/methodology questions (Jira usage was adequate but not standout)

**Improvement from practice:**
- Held position under Neil's pushback (tech debt analogy) -- practiced this
- Led with recommendation before supporting arguments -- improvement from Mar 4 practice
- Market timing argument was new and strong -- emerged naturally, not practiced
- Communication plan still came after the recommendation rather than as part of it

## Andrea's Questions & What They Revealed About the Role

### Lindsie's Half-Hat (what she's been covering)
- **Voice of the customer:** Centralized customer voice for product discovery
- **Tooling:** Tried Productboard, wasn't working well for teams. Switched to Reforge.
- **AI Customer Committee:** Includes designers and PMs, but very ad hoc -- not consistently functioning. Needs ownership.
- **Product development lifecycle:** Working deeply with Neil to simplify it and protect for AI-driven changes. Roles are starting to collapse with AI.

### Neil's Half-Hat (what he needs)
- **Bridge R&D to GTM:** Biggest gap. Needs support connecting R&D to the rest of the org.
- **Communication cadence:** Needs regular, organized communication. Has been a challenge.
  - R&D town halls: monthly (briefly moved to quarterly, going back to monthly)
  - Company town halls: quarterly
- **AI and org structure:** Karpathy's tweet (agentic engineering didn't work until Dec 2025) gave Neil pause about restructuring engineering teams. Review/discussion scheduled for next Monday.

### The Role = Lindsie's Half + Neil's Half
This role is explicitly the combination of what Lindsie and Neil have each been partially covering. They need a dedicated person for:
1. Customer voice and product discovery operations
2. Cross-functional tooling and process (what works, what doesn't)
3. AI committee ownership and coordination
4. Product development lifecycle management
5. R&D-to-GTM bridge (communication, reporting, alignment)
6. Change management as AI reshapes roles and workflows

### AI Strategy Context
- **18-month roadmap to be AI-native**, established late fall 2025
- Goal: add meaningful AI throughout user journey to **remove toil** (non-necessarily frictional pieces of complex workflows)
- Looking to market the product as **agentic** shortly
- AI in product AND internal workflows -- means to an end for better/faster outcomes
- Mixed feelings across org -- leadership navigating respectfully
- Focus on psychological safety for experimentation (Neil echoed Andrea's earlier point)
- Neil: allowing people to feel comfortable to collaborate, experiment, and empower themselves

### Key Insight for Andrea
Neil and Lindsie essentially described the job description to you unprompted. They're not just hiring for a role -- they're looking for someone to take real problems off their plates that they've been partially solving themselves. The AI committee, the PDLC simplification, the R&D-GTM bridge, the change management -- these are all active pain points, not hypothetical responsibilities. This is a strong signal that the role has real scope and real support from leadership.