Problem Interview Examples for B2B SaaS

Sketched B2B SaaS problem interview examples. Names and details are illustrative. Steal the patterns.

Example 1: User Interview - Ops Manager

Founder: "Walk me through the last time your team built a campaign report."

Interviewee: "Pulled data from Salesforce, dropped into a sheet, our analyst added margins, re-imported into the BI tool. Two days for what should be a one-hour task."

Founder: "Where did the two days go?"

Interviewee: "The Salesforce export keeps changing schema. We rebuild the sheet template every month."

Notes: Tools: Salesforce, sheets, BI tool. Pain: schema drift on export, monthly rebuild. Vocabulary: "rebuild the template," "schema keeps changing."

Example 2: Buyer Interview - Director

Founder: "Walk me through the last vendor you approved."

Interviewee: "Six month process. Security review, IT integration check, finance ROI model. The team that wanted it had to build a one-page memo defending the spend versus our existing tools."

Founder: "What kills deals at your stage?"

Interviewee: "Vendor consolidation pressure. If we already have a tool that kind of does it, the new tool has to be dramatically better or it gets cut."

Notes: Cycle - 6 months. Constraints: security, IT, finance. Killer: consolidation pressure. The team building the memo is the champion. ROI model is required artifact.

Example 3: Gatekeeper Interview - Head of Security

Founder: "What does your vendor review look like?"

Interviewee: "SOC 2 Type II minimum. Data residency in US or EU. SSO/SAML. We will not approve anything without those three."

Founder: "What might let you make an exception?"

Interviewee: "Pre-deployment pen test results, willingness to sign DPA with our addendums, named security contact. Even then, slow process."

Notes: Hard floor: SOC 2 II, residency, SSO. Soft floor: pen test, DPA flexibility, named contact. Without the hard floor, no deal.

What These Share

Each interview surfaces different layers. Users surface workflow texture and tool stack. Buyers surface decision criteria and consolidation politics. Gatekeepers surface compliance baselines. The product spec is the union of all three.

Stealing the Pattern

Same shape across all three: open-ended past-tense story prompt, two follow-ups, capture exact phrases, never pitch. The role-specific question varies. The interview discipline does not.

What Bad Examples Look Like

Bad: founder pitches user immediately. User says "sounds great." Founder skips buyer and gatekeeper. Builds product. Cannot pass procurement at any of the user's companies. Three months wasted.

The good examples sound ordinary because the discipline is in what is not happening - no pitch, no demo, no leading.