Monika's email says "assessing your storytelling skills through a presentation of your work." This is not a case interview or a technical screen. Jonathan wants to see how you communicate about your own work to an executive audience.
Likely structure (1 hour):
- 5 min — reintroduction, small talk
- 15–20 min — you walk through the presentation
- 20–25 min — Jonathan probes: follow-up questions, "tell me more about X"
- 10–15 min — your questions, closing
Key Insight
Jonathan comes from an engineering background and, per your HM notes, "seems to lack narrative skill." He's hiring someone who complements him. This interview is the proof point. He's not evaluating whether your slides are pretty — he's evaluating whether you can take a complex operation and make it legible, memorable, and actionable for different audiences.
The deck content is Ting's business operations. But the story Jonathan should walk away with is about you and how you work.
Frame it up front
Before you open the first slide, set the context in ~60 seconds:
Opening Frame
"This is a deck I created to onboard new team members — people on my team and cross-functional partners. I worked very closely with operational teams like CS, and a lot of their work was manual — it required thorough training and a full understanding of how the business actually worked. But I realized the problem wasn't just CS onboarding. Every team understood their piece but not how it connected upstream, downstream, or in parallel with other teams. So I built this to give everyone a shared mental model of the whole operation — all the illustrations are mine, done on iPad — and I presented it regularly across the org. It also became the foundation for when I needed to present more detailed technical topics — the platform architecture, how systems and tools fit together to drive business outcomes. People could absorb the technical detail because they already had this map."
Why this matters
The deck had a layered purpose:
- Operational enablement — CS and other manual-heavy teams needed to understand the full lifecycle to do their jobs well, not just their stage
- Cross-functional orientation — every team could see where they fit relative to upstream/downstream/parallel work
- Foundation for deeper technical conversations — when you later presented the internal platform, systems architecture, or tool integrations, people had the business context to understand why those systems existed and how they drove outcomes
This is the exact progression Jonathan needs at Procurify: shared understanding first, then layer in the technical and strategic detail.
What this signals about you
| What Jonathan Sees | What It Maps To In the Role |
|---|
| Saw a gap, created the artifact unprompted | Initiative & ownership — "not dropping the ball" |
| End-to-end business model, not just your domain | Cross-functional visibility a CPTO advisor needs |
| Built for operational teams with manual workflows | Understands ground-level operations, not just strategy from above |
| Used as scaffolding for deeper technical presentations | Layers communication — mental model first, then detail. Exactly what board/exec storytelling requires |
| Hand-drawn illustrations + clean structure | Communication craft — storytelling pillar from HM interview |
| Designed for reuse, presented many times | Building cadence & operating rhythms, not one-offs |
| Tools mapped to each stage | Systems thinking — understanding the tool landscape |
| "Major oversimplification" subtitle | Knows how to calibrate fidelity for the audience |
Don't narrate every bullet. Hit the key points, linger where the story is richest, and keep total walkthrough to 15–20 min.
Slides 1–2: Title + Product Context
Brief. Establish what Ting is (fiber internet ISP, community-focused, multiple markets). Don't over-explain — the audience is Jonathan, not a new hire.
Slides 3–4: Business Operations Overview
This is your strongest moment. The 6-stage hand-drawn diagram is the centerpiece. Talk about why you structured it this way — the full lifecycle from market selection to post-activation. Mention the illustrations were deliberate: approachable, memorable, lower the barrier to understanding.
Storytelling Angle
"I wanted people to see the whole picture before they zoomed into their piece. The hand-drawn style was intentional — it signals 'this is a mental model, not a spec doc.' People remember sketches differently than they remember bullet points."
Slides 5–9: Stage Deep Dives
Don't go through all 6 in equal depth. Pick 2–3 where you have the best stories:
| Stage | Why Linger Here |
|---|
| Market Development (5) | Strategic — partner selection, competitive positioning. Parallels Procurify's mid-market targeting |
| Customer Acquisition (8) | Cross-functional — spans digital, door-to-door, cold calls. You owned the GTM tool stack (HubSpot, GA4). Ties to your Lalamove growth stories |
| Order Fulfillment (9) | Operational complexity — the Tingfecta tools, provisioning systems. Connects to your beta program and migration narratives |
For the other stages, acknowledge them briefly: "I'll move through these faster, but happy to go deeper on any."
Slide 10: The Tingfecta Architecture
This is your systems thinking slide. Walk through how the systems connect, the residential vs. commercial split, and the Zapier integration. This is where you show you understand the tool ecosystem, not just individual workflows.
Procurify Connection
Procurify has a similar multi-tool landscape (Jira, Intercom, Salesforce, Vitally, Notion, Figma, etc. — per Neil and Lindsie's interview). Jonathan needs someone who can map and rationalize that. This slide proves you've done it before.
Slide 12: Acquisitions
Brief but important. Mention the complexity of integrating acquired companies with different tech stacks, product types (aerial vs. underground fiber, copper, fixed wireless). This is the "gift card anecdote" territory from your Tony Wang interview — acquired companies bring legacy workflows that need evaluation.
Slides 13–14: Learn More / Resources
If redacted, skip or use as a closing: "The full version had links to our internal knowledge bases and documentation — which I also built and maintained."
Jonathan's HM interview questions were about communication style, product taste, process improvement, and business acumen. Expect him to probe the same themes through the lens of your deck.
Why did you create this? What problem were you solving?
I worked closely with operational teams like CS where a lot of the work was manual — they needed deep understanding of the full business to do their jobs, not just their slice. But the same gap existed everywhere: teams understood their own stage but not how they connected upstream, downstream, or in parallel. I built this so everyone had the same map. It also became the foundation for deeper technical conversations later — when I presented the internal platform or how systems fit together, people could absorb it because they already had the business context.
How did you decide what to include vs. leave out?
The subtitle says it — "a representative but major oversimplification." I optimized for mental model, not completeness. Each stage has one illustration, one "what we do" summary, and the key tools. If someone needed more depth, they could go to the knowledge base (which I also maintained). The goal was: after 30 minutes with this deck, you could draw the business on a whiteboard from memory.
Did this evolve over time? How?
Yes — every time I presented it, I noticed which parts generated questions and which didn't land. The architecture diagram (Tingfecta) was added later because people kept asking how the tools connected. The acquisitions slide was added when we started getting new hires from acquired companies who needed to understand where they fit.
What impact did it have?
Four things: (1) Faster onboarding — people ramped faster because they had shared language from day one. (2) Better cross-functional conversations — when I referenced "stage 4" or "the order fulfillment flow," people knew what I meant. Teams could see their upstream/downstream dependencies. (3) It became the default reference — other teams started pointing new hires to it independently. (4) It made my later technical presentations land harder — when I walked teams through the internal platform architecture or how tools connected, they already had the business map to anchor on. I didn't have to re-explain why something mattered.
How do you think about storytelling and communication for a board or exec audience vs. this onboarding context?
Different fidelity, same principle. For onboarding, the goal is "understand the whole, then go deep." For a board, the goal is "here's what matters, here's what we're doing about it, here's what we need." I use the same approach — visual-first, concise at the top with depth available for drill-down. I actually described this exact structure in my problem-solving round with Lindsie and Neil.
Tell me about the migration / platform work you did at Ting.
This is your strongest narrative — it landed in HM round, with Fred, Tony, Lindsie, and Neil. Keep it tight: phased rollout of internal platform, beta program that surfaced provisioning incompatibility, data-driven decision to rebuild, managed GTM pain through market sequencing, demonstrated value at the end. You've told this story 5+ times now; trust the muscle memory.
How would you apply this kind of thinking at Procurify?
Procurify is in transformation mode — new CEO, new CPTO, AI-native strategy, 18-month roadmap. From what I've learned in the panel rounds, the R&D-to-GTM bridge is a real gap. The AI committee needs ownership. The product development lifecycle is being reworked. All of that requires the same thing this deck represents: someone who maps the whole system, creates shared understanding, and gives people a common language to work from. That's what I do.
Pacing
- Don't read the slides. You've presented this many times — use that. Talk to Jonathan, glance at slides for structure.
- Linger on the overview diagram (slide 4). This is your architectural centerpiece. You can verbally reference the deeper technical docs (integration maps, platform flowcharts) without needing to show them.
- Move through the stage deep dives briskly unless Jonathan asks you to slow down.
- Leave room for questions. If Jonathan interrupts with a question, welcome it — it means he's engaged. Don't rush to get back to your slides.
Tone
- Conversational, not rehearsed. You're walking a colleague through your work, not pitching investors.
- Show ownership: "I noticed...", "I built...", "I decided..." Not "the team" or "we."
- Be honest about limitations: "This was a simplification and I knew it — the real operations were significantly more complex, and that's why the knowledge base existed as the deeper layer."
Closing strong
Closing Frame
After the walkthrough and Q&A, bring it back: "What I want to leave you with is that this deck is how I think about my role — understanding the whole system, making it legible for everyone, and giving people a shared language to work from. That's what I'd bring to Procurify."
Watch Out For
Don't over-explain Ting's business. Jonathan doesn't need to deeply understand fiber internet operations — he needs to see how you think, communicate, and create clarity from complexity. Keep the emphasis on your approach and choices, not on ISP industry details.
You've talked to 6 people now and know a lot about the role. Use this round to go deeper with the person you'd report to directly.
High-value questions
- "What does the first 90 days look like for this person?" — Gets at his expectations and priorities. You already know from Lindsie/Neil what the pain points are; see if Jonathan's priorities match.
- "I heard R&D town halls were monthly, moved to quarterly, and are heading back to monthly. What drove those changes, and what do you want the cadence to look like going forward?" — Shows you already know the current state from Neil/Lindsie. Gets Jonathan to reveal what he thinks isn't working and what he'd want this role to own. Much stronger than asking the open-ended version because it signals you've done your homework and are thinking about execution, not just discovery.
- "How do you like to receive information — what format, cadence, and level of detail works for you?" — You're going to be his trusted advisor. Understand his operating style.
- "Where is the AI-native roadmap right now — are you in the 'what to build' phase or the 'how to execute' phase?" — Shows you understand the 18-month timeline and are thinking about where you'd plug in.
Avoid
Don't ask questions the panel already answered (tool stack, team structure, AI adoption status). Jonathan will know you've talked to his team. Ask things only he can answer — his priorities, his working style, his vision.
If Jonathan doesn't have a clear answer on the first 90 days, drive the conversation forward with this proposal and seek his input. Frame it as: "Here's how I'd approach it based on what I've learned from the team — I'd love your perspective on what I'm missing or what you'd reprioritize."
First 30 Days — Learn & Map
| Do | Outcome |
|---|
| Understand the vision |
Absorb existing vision, mission, KPIs, and objectives. Don't change anything yet — understand why things are the way they are. |
| 1:1s with key people |
Introduce yourself across every team. Establish rapport before establishing process. |
| Learn the business |
Key customers, features, timelines, revenue levers, operational gaps. |
| Get into the tools |
Access everything, familiarize with data and use cases firsthand. |
30-Day Deliverable
Identify three things:
- Key nodes in the org — people who may not be leaders/managers but hold deep institutional knowledge, people who are sociable and have great relationships with colleagues, and people who have a multiplier effect on those around them
- Existing levers for efficiency and productivity that are underused or unrecognized
- Communication and operational gaps — where information is getting lost between teams
Days 30–60 — Build the Infrastructure
| Do | Outcome |
|---|
| Establish comm cadence |
Regular cross-functional touchpoints — what, to whom, how often. |
| Create comm artifacts |
Different fidelity for different audiences: C-level & board vs. team leaders vs. ICs/frontline. |
| Dashboards & trackers |
Structure and support progress tracking across the existing tooling. |
| Tools audit |
Work with IS/IT to verify existence and validity of tools mapping — integrations, data storage and flows, contracts, use cases. |
60-Day Deliverable
- Informal alignment tests show improvement over baseline from day 30 — increased use of shared language, fewer "I didn't know about that" moments
- Strengthened understanding of shared vision and mission, distilled into something catchy and meaningful that people actually repeat
- Simplified, focused views on upcoming targets that add up meaningfully to a broader strategy and roadmap
Days 60–90 — Optimize & Deliver
| Do | Outcome |
|---|
| Refine cadence |
Adapt or pare down communication cadence based on what's working and what's noise. |
| Pilot opportunities |
Evaluate if there are tools or approaches from my own work that could be deployed as quick wins (e.g., internal feedback/pulse tooling). |
| Tech stack rationalization |
Revise internal tech stack as needed to simplify hand-off of work between teams. |
90-Day Deliverable
- Quarter goals reached or exceeded
- Significant reduction in third-party vendor contract costs
- A clear, understood distinction across the org on how to balance process vs. judgment — how to protect quality and promote speed
- First-pass recommendations on org structure changes — informed by 60 days of 1:1s, tools audit, and observed communication patterns. Not a reorg proposal, but a point of view grounded in evidence.
Why This Lands
This plan mirrors the layered approach from the deck itself: map the whole system first (30d), build the communication infrastructure (60d), then optimize and deliver (90d). If Jonathan asks "how would you start?" — you've already shown him the answer through your presentation.