interview_prep_doc / art_VtooVhwHZnU

Content

{
  "markdown": "# Fivetran Interview Prep\n## Questions to Ask Casey Karst\n\n---\n\n## 1. Interviewer Summary\n\nCasey Karst joined Fivetran in June 2025 as a Principal Product Manager, focused on making it easier for customers to develop and deploy Managed Data Lakehouses. He is relatively new to Fivetran himself \u2014 roughly a year in \u2014 which means he is both a credible insider and someone who is still forming his own read on the company's culture and direction. That shared \"new joiner\" orientation is worth keeping in mind: he may be candid in ways a longer-tenured employee might not be.\n\nBefore Fivetran, Casey spent about 18 months as Director of PM at Dremio, where he owned Catalog and Engine simultaneously \u2014 Apache Iceberg, Apache Polaris, query planning, and dbt integration. That is a wide technical surface area, and it signals someone comfortable holding complexity. Prior to Dremio, he was the founding PM at RelationalAI, where he owned customer onboarding, security, and scale-out computation from scratch. And before that, nearly eight years at Microsoft on Azure SQL Data Warehouse and PolyBase \u2014 deep roots in enterprise data infrastructure at cloud scale.\n\nHis background at Splunk is the most direct shared context with Felix. Casey built Splunk Data Manager to automate cloud data ingestion from Azure, M365, AWS, and GCP \u2014 a direct parallel to Felix's work on Search Orchestration, the Search Service, and SPL at Splunk Cloud Services. Felix also led Splunk Logging-as-a-Service at Kaiser Permanente. That overlap is a genuine rapport anchor, not a forced connection.\n\nA few things to keep in mind going into this conversation:\n\n- **Expect the conversation to lean technical.** Casey has an engineering foundation (Olin College, mechanical engineering) and a career built on data infrastructure. He will likely appreciate first-principles thinking over product-speak.\n- **The Fivetran\u2013dbt Labs integration is the dominant strategic variable.** Casey joined during this transition; he may have limited visibility into how the combined org ultimately shakes out. Ask about it with curiosity, not assumption.\n- **His career has been non-linear by design.** He moved from Director at Dremio back to Principal at Fivetran \u2014 almost certainly a deliberate choice for domain fit and company trajectory. Do not reference this as a step back; it is not.\n- **He values inflection points.** Founding PM at RelationalAI, early at Dremio, joining Fivetran mid-integration \u2014 there is a clear pattern of choosing pivotal moments over safe ones. That framing will resonate with him.\n\nThis conversation is likely to be substantive and peer-level. Thoughtful questions that demonstrate technical depth, strategic awareness, and genuine curiosity about his experience will land better than surface-level role questions.\n\n---\n\n## 2. Best Questions to Ask Casey Karst\n\n---\n\n### A. Interviewer Experience and Rapport\n\n**Question 1.**\n> **\"You were the founding PM at RelationalAI and came in early at Dremio \u2014 and now you're at Fivetran during what sounds like a significant inflection point with the dbt Labs integration. What draws you to these early or pivotal moments at companies, and what's been different about this particular chapter at Fivetran?\"**\n\n**Why this is a good question:** It opens a genuine conversation about Casey's career philosophy rather than his r\u00e9sum\u00e9. It signals you've read his trajectory carefully \u2014 not just his current title \u2014 and it invites him to share what he finds energizing about the current moment. His answer will tell you a great deal about how he frames the opportunity and what he thinks is actually at stake.\n\n---\n\n**Question 2.**\n> **\"At Dremio you were driving both Catalog and Engine simultaneously \u2014 Apache Iceberg, Polaris, query planning, dbt integration. That's a wide surface area. How did you think about prioritization across those workstreams, and are there lessons from that experience you're applying to how you structure product work at Fivetran now?\"**\n\n**Why this is a good question:** It demonstrates you understand the technical breadth of his Dremio work \u2014 not just the job title \u2014 and invites him to share real prioritization frameworks he actually uses. This is useful intelligence for how the Enterprise Platform team operates day-to-day, and it positions you as someone who thinks about PM craft, not just product outcomes.\n\n---\n\n**Question 3.**\n> **\"Your time at Microsoft on PolyBase and Azure SQL Data Warehouse gave you a long view on how enterprise data loading has evolved. From where you sit now at Fivetran, what feels most different about the current generation of data infrastructure challenges compared to what you were solving in the Azure era?\"**\n\n**Why this is a good question:** This leverages his deepest technical roots to spark a substantive conversation. It signals that you are thinking about the historical arc of the space \u2014 not just the current product backlog \u2014 and it gives him room to share a perspective he has probably developed over a decade but rarely gets asked about directly.\n\n---\n\n### B. Shared Context \u2014 Splunk and Platform Work\n\n**Question 4.**\n> **\"We overlapped at Splunk \u2014 you were building Splunk Data Manager to automate cloud data ingestion from AWS, Azure, and GCP, and I was on the Search Orchestration side owning the Search Service and SPL. I'm curious how you think about the lessons from that era of cloud-native data pipelines and what carried forward into your work at Dremio and now Fivetran.\"**\n\n**Why this is a good question:** This is the most direct shared context in the entire conversation. Both worked at Splunk during overlapping periods on adjacent problems \u2014 Casey automating data ingestion, Felix owning the query and orchestration layer those pipelines fed into. This is a genuine rapport-builder and a substantive technical conversation starter, not a manufactured connection. Use it early.\n\n---\n\n**Question 5.**\n> **\"At Intuit I spent a lot of time on developer-facing platform infrastructure \u2014 SDKs, DevPortal, self-service onboarding \u2014 and one of the hardest problems was balancing the needs of internal platform consumers with the velocity demands of product teams. Given your experience as the founding PM at RelationalAI where you owned onboarding and security simultaneously, how did you navigate that tension, and do you see a similar dynamic on the Enterprise Platform team here?\"**\n\n**Why this is a good question:** This connects Felix's Intuit platform experience directly to Casey's RelationalAI founding PM work, establishing peer credibility on a shared operational challenge. It also surfaces a real tension that any platform PM at Fivetran would face \u2014 and Casey's answer will tell you how the team currently navigates it.\n\n---\n\n### C. Role and Team Dynamics\n\n**Question 6.**\n> **\"The role spans enterprise security and governance, workspace configuration, and observability tooling \u2014 that's a meaningful surface area. How is that scope currently divided across PMs on the Enterprise Platform team, and where would a new senior PM be expected to take the most ownership soonest?\"**\n\n**Why this is a good question:** Gets concrete about team structure and where the real leverage is. Understanding which area is most urgent \u2014 and most under-resourced \u2014 helps you assess fit, set realistic expectations, and signal the right strengths in the conversation.\n\n---\n\n**Question 7.**\n> **\"What does success look like at 30, 60, and 90 days in this role \u2014 and how much of that is about shipping versus listening and orienting?\"**\n\n**Why this is a good question:** The ramp expectation tells you whether the team needs a builder or a strategist first, and how much runway you have to develop domain fluency before you're expected to drive outcomes. It also surfaces whether the team has thought carefully about onboarding \u2014 a signal in itself.\n\n---\n\n**Question 8.**\n> **\"What's the most pressing unsolved problem on the Enterprise Platform roadmap right now \u2014 the thing that keeps the team up at night or that customers are loudest about?\"**\n\n**Why this is a good question:** This surfaces the real pain points rather than the polished narrative. It gives you a chance to react with relevant experience in real time, and it tells you whether the team has a clear-eyed view of its own gaps or is still working through prioritization.\n\n---\n\n**Question 9.**\n> **\"How does the Enterprise Platform team interface with the connector and pipeline teams day-to-day? Is the relationship more of an internal platform provider, a peer collaborator, or something else?\"**\n\n**Why this is a good question:** Understanding the internal customer dynamic is critical for a platform PM. This tells you how much influence you'd have, how decisions get made when priorities conflict, and whether the team operates more like a shared service or a product team with its own roadmap authority.\n\n---\n\n### D. Technical Environment\n\n**Question 10.**\n> **\"The JD mentions enterprise-grade security and governance \u2014 SSO, RBAC, audit logging. How mature is Fivetran's current implementation of those capabilities, and where are the biggest gaps that this role would be expected to close?\"**\n\n**Why this is a good question:** Gets specific about the technical state of the product rather than accepting a polished surface-level answer. Knowing where the real gaps are \u2014 versus where the product is already strong \u2014 tells you what kind of work you'd actually be doing in year one.\n\n---\n\n**Question 11.**\n> **\"Given your work at Dremio on Apache Iceberg and Polaris, and Fivetran's positioning around the Managed Data Lakehouse \u2014 how much does the Enterprise Platform PM need to engage with open table format standards and lakehouse architecture decisions, versus focusing purely on the platform layer above them?\"**\n\n**Why this is a good question:** Connects Casey's specific technical expertise to the role scope in a way that only someone who has read his background carefully could ask. It also helps you understand how deep the technical engagement goes for this PM seat \u2014 important for calibrating whether the role would stretch you in the right directions.\n\n---\n\n**Question 12.**\n> **\"How does the team currently handle observability and telemetry for the platform itself \u2014 are PMs expected to get into the data directly, or is there a data/analytics function that mediates that?\"**\n\n**Why this is a good question:** Directly relevant to Felix's background doing SQL and BigQuery analysis at Intuit to prioritize developer pain points. This helps you understand how much self-serve data access you'd have and whether your analytical instincts would be well-utilized \u2014 or whether you'd be dependent on a data team for every question.\n\n---\n\n### E. Culture and Working Style\n\n**Question 13.**\n> **\"You've been at companies ranging from a startup like RelationalAI to Microsoft's scale. How would you characterize Fivetran's operating style right now \u2014 especially as the dbt Labs integration is underway? Does it feel more like a scaling startup or an enterprise software company in how decisions get made?\"**\n\n**Why this is a good question:** The merger creates genuine cultural uncertainty that a polished recruiting answer won't fully address. Framing this through Casey's own experience across company sizes makes it feel like a peer conversation rather than an interrogation \u2014 and his answer will tell you something real about the current operating environment.\n\n> *Softened version if the moment calls for it:* **\"From what you've experienced so far at Fivetran \u2014 especially coming from Dremio's environment \u2014 how would you describe the day-to-day operating rhythm here?\"**\n\n---\n\n**Question 14.**\n> **\"When a PM and an engineering lead disagree on scope or approach for a platform feature, how does that typically get resolved here? Is there a strong culture of data-driven escalation, or does it come down to relationship and influence?\"**\n\n**Why this is a good question:** Tells you how much organizational capital matters versus analytical rigor \u2014 important for calibrating how to operate effectively. It also signals that you've navigated this tension before and are thinking about it seriously.\n\n---\n\n**Question 15.**\n> **\"How much autonomy does a Senior PM on this team have to define their own roadmap versus inheriting a largely pre-set direction from leadership?\"**\n\n**Why this is a good question:** Critical for understanding whether this is a role where you'd be building strategy or executing someone else's vision. The answer also tells you how much the team trusts senior ICs to drive direction versus treating them as execution resources.\n\n---\n\n### F. Growth and Development\n\n**Question 16.**\n> **\"You've optimized across your career for impact and domain fit over a straight title trajectory. For a Senior PM joining this team, what's the realistic growth path, and how does Fivetran think about promotion versus lateral growth?\"**\n\n**Why this is a good question:** Frames the question around Casey's actual career choices \u2014 non-linear, impact-driven \u2014 rather than assuming a standard ladder. This framing is more authentic and more likely to get a candid answer than a generic \"what's the growth path here?\" question.\n\n> *Note:* Do not reference his move from Director at Dremio to Principal at Fivetran as a \"step back.\" Frame it as a deliberate, values-driven choice \u2014 which it almost certainly was.\n\n---\n\n**Question 17.**\n> **\"Given that this role sits at the intersection of data infrastructure, enterprise security, and platform extensibility \u2014 are there opportunities to develop deeper expertise in areas like lakehouse architecture or open standards work, or does the PM role stay more at the product layer?\"**\n\n**Why this is a good question:** Signals intellectual curiosity about the technical domain and helps you assess whether the role would stretch you in directions that align with your longer-term trajectory. It also gives Casey a chance to share what he finds intellectually engaging about the space.\n\n---\n\n### G. Strategy and Vision\n\n**Question 18.**\n> **\"With the Fivetran and dbt Labs integration underway, how does the Enterprise Platform team's roadmap change \u2014 or does it? Are there new platform capabilities that only make sense in the combined company context?\"**\n\n**Why this is a good question:** The merger is the biggest strategic variable right now. Understanding how it reshapes the platform roadmap \u2014 or whether it does at all \u2014 is essential for evaluating the role's trajectory and the team's direction over the next 12\u201324 months.\n\n> *Handle carefully:* Casey has been at Fivetran for about a year and may have limited visibility into how the combined org will ultimately be structured. Ask with genuine curiosity, not as a test. If he says \"we're still figuring that out,\" that's a useful and honest answer.\n\n---\n\n**Question 19.**\n> **\"The JD mentions keeping an eye toward AI-first opportunities. What does that concretely mean for the Enterprise Platform team \u2014 are there specific AI-native features on the horizon, or is it more about ensuring the platform is a reliable substrate for customers building AI applications?\"**\n\n**Why this is a good question:** Separates genuine AI strategy from marketing language. The answer tells you where you'd actually be investing time \u2014 and whether the team has a specific AI thesis or is still exploring what \"AI-first\" means for a platform that moves data.\n\n---\n\n**Question 20.**\n> **\"Where do you see the biggest competitive pressure on Fivetran's enterprise platform capabilities over the next 18\u201324 months \u2014 is it from hyperscalers building native data movement, from open-source tooling, or from somewhere else?\"**\n\n**Why this is a good question:** A strategic question that invites Casey to share his honest competitive read. It signals you're thinking about the market context, not just the product backlog \u2014 and it gives him room to share a perspective he's probably formed but doesn't always get asked about directly.\n\n---\n\n## 3. Best Conversation Starters\n\nThese are designed for the first 2\u20133 minutes of the call, before the formal question-and-answer rhythm sets in.\n\n### The Splunk Connection\n> **\"I saw you were at Splunk around the same time I was \u2014 you were building Data Manager to automate cloud log ingestion and I was on the Search Orchestration side. Small world. I'd love to hear how that experience shaped how you think about data pipeline automation now.\"**\n\n### The Lakehouse Arc\n> **\"Your path from PolyBase at Microsoft to Iceberg and Polaris at Dremio to Managed Data Lakehouses at Fivetran feels like you've been tracking the evolution of the data warehouse-to-lakehouse shift from the inside for over a decade. That's a pretty rare vantage point.\"**\n\n### The Founding PM Question\n> **\"I noticed you were the founding PM at RelationalAI \u2014 I've always been curious what it's like to be the first PM at a company with that kind of novel technical approach. What was the hardest part of figuring out what to build first?\"**\n\n---\n\n## 4. Topics to Handle Carefully\n\n### Casey's Title Trajectory\n**The risk:** Casey moved from Director of PM at Dremio back to Principal PM at Fivetran. Raising this \u2014 even obliquely \u2014 could come across as presumptuous or awkward. He almost certainly made a deliberate choice based on domain fit, company trajectory, or the specific opportunity.\n\n**Ask this instead:**\n> **\"You've clearly been selective about the moments you join companies \u2014 what made Fivetran the right move at this point in your career?\"**\n\nThis invites him to share his reasoning on his own terms, without implying any judgment about the title.\n\n---\n\n### The Fivetran\u2013dbt Labs Integration\n**The risk:** The organizational picture is genuinely unsettled. Questions that presuppose clean org structures, stable roadmaps, or settled team boundaries may put Casey in an uncomfortable position \u2014 especially since he joined during the transition and may not have full visibility himself.\n\n**Ask this instead:**\n> **\"I imagine the integration with dbt Labs is still taking shape in a lot of ways \u2014 from your vantage point, what feels most clarified and what's still in flux?\"**\n\nUseful softening phrases:\n- *\"From what you've seen so far...\"*\n- *\"Even if it's early days...\"*\n- *\"I know this is probably still evolving, but...\"*\n\n---\n\n### Fivetran's Historical Product Decisions\n**The risk:** Casey has only been at Fivetran for about a year. Questions that assume deep institutional knowledge about Fivetran's historical product choices, past roadmap decisions, or long-standing cultural norms may put him on the spot in ways that aren't useful for either of you.\n\n**Ask this instead:** Ground questions in his direct experience \u2014 *\"In the time you've been here...\"* or *\"From what you've observed so far...\"* \u2014 rather than asking him to speak for the whole company's history.\n\n---\n\n## 5. Best Questions to Prioritize During the Call\n\nIf the conversation moves quickly and you only have time for five questions, these are the highest-signal ones:\n\n1. **Question 4 (Splunk overlap)** \u2014 The strongest rapport anchor in the conversation; use it early to establish peer credibility and a genuine shared reference point.\n2. **Question 8 (most pressing unsolved problem)** \u2014 Surfaces the real state of the roadmap and gives you a chance to react with relevant experience in real time.\n3. **Question 6 (scope and ownership)** \u2014 Gets concrete about where you'd actually spend your time and what the team needs most urgently.\n4. **Question 18 (dbt Labs integration and roadmap)** \u2014 The biggest strategic variable; understanding how it reshapes the platform team's direction is essential for evaluating the role.\n5. **Question 13 (operating style)** \u2014 The merger creates genuine cultural uncertainty; Casey's honest read on how the company operates right now is hard to get elsewhere.\n\n---\n\n## 6. Suggested Call Flow\n\n### Opening \u2014 Establish Rapport (first 2\u20133 minutes)\nLead with the Splunk connection. It's genuine, specific, and immediately establishes that you've done your homework and have real shared context.\n\n> **\"I saw you were at Splunk around the same time I was \u2014 you were building Data Manager and I was on the Search Orchestration side. I'd love to hear how that experience shaped how you think about data pipeline automation now.\"**\n\n### After Discussing Background \u2014 Go Deeper on His Experience\nOnce the rapport is warm, move into one of the career philosophy questions:\n\n> **\"You've clearly gravitated toward pivotal moments at companies \u2014 founding PM at RelationalAI, early at Dremio, and now Fivetran during the dbt Labs integration. What draws you to those inflection points, and what feels different about this chapter?\"**\n\n### When Discussing the Role \u2014 Get Concrete\nShift to the role and team questions to gather real signal:\n\n> **\"The scope spans security, governance, workspace config, and observability \u2014 where would a new senior PM be expected to take the most ownership soonest?\"**\n\n> **\"What's the most pressing unsolved problem on the Enterprise Platform roadmap right now?\"**\n\n### Near the End \u2014 Strategic and Growth Questions\nSave the bigger-picture questions for when the conversation has warmed up:\n\n> **\"With the dbt Labs integration underway, are there new platform capabilities that only make sense in the combined company context?\"**\n\n> **\"For a Senior PM joining this team, what does the realistic growth path look like \u2014 and how does Fivetran think about promotion versus lateral growth?\"**\n\n### Closing \u2014 A Recruiter-Friendly Question\nEnd on a forward-looking note that signals genuine enthusiasm:\n\n> **\"What would make you feel like this hire was a home run six months from now?\"**\n\n---\n\n## 7. Final Recommended Question Set\n\nIf time is short \u2014 or if the conversation runs long and you need to triage \u2014 ask these four to six questions:\n\n1. **The Splunk connection** \u2014 *\"We overlapped at Splunk \u2014 you on Data Manager, me on Search Orchestration. How did that era shape how you think about data pipeline automation now?\"*\n2. **Most pressing unsolved problem** \u2014 *\"What's the thing on the Enterprise Platform roadmap that keeps the team up at night right now?\"*\n3. **Scope and earliest ownership** \u2014 *\"Where would a new senior PM be expected to take the most ownership soonest?\"*\n4. **dbt Labs integration and roadmap** \u2014 *\"How does the dbt Labs integration change the Enterprise Platform roadmap \u2014 or does it?\"*\n5. **Operating style** \u2014 *\"How would you characterize Fivetran's operating style right now, especially mid-integration?\"*\n6. **Definition of success** \u2014 *\"What would make you feel like this hire was a home run six months from now?\"*\n\n---\n\n## 8. Strong Closing Line\n\nUse this \u2014 or a version of it \u2014 to close the conversation:\n\n> **\"I've spent the last several years building developer-facing platform infrastructure at Intuit and working on search orchestration at Splunk, and what I keep coming back to is the challenge of making complex, enterprise-grade systems feel simple and trustworthy to the people who depend on them. That's exactly what this role is about \u2014 and hearing how you're thinking about the platform's direction here makes me even more interested in being part of it.\"**\n\n---\n\n## 9. Final Reminder\n\nThis conversation should demonstrate:\n\n- **Technical depth without posturing** \u2014 Casey has an engineering background and will see through product-speak; speak precisely about systems, tradeoffs, and data.\n- **Genuine curiosity about his experience** \u2014 The best questions here are ones you actually want the answers to; let that show.\n- **Peer-level confidence** \u2014 You have 12+ years of relevant experience across Splunk, Intuit, and platform infrastructure; this is a peer conversation, not an audition.\n- **Strategic awareness** \u2014 Show that you're thinking about the Fivetran\u2013dbt Labs integration, the competitive landscape, and the long-term platform direction \u2014 not just the day-to-day role.\n- **Shared context, used well** \u2014 The Splunk overlap is real and specific; use it as a genuine conversation anchor, not a name-drop.\n- **Intellectual honesty** \u2014 If something is unclear or uncertain (especially around the integration), it's fine to acknowledge that \u2014 Casey is likely navigating the same uncertainty.",
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}