A composited case from a real engagement (anonymised, with details adjusted enough to protect the client). A healthcare startup that needed to pivot in 90 days. Here's the day-by-day of what we did, what worked, what didn't, and what I'd redo if I could rewind.
The starting position
The company had built a B2B SaaS product for hospital operations — patient flow optimisation, specifically. They had ~15 customers, $2.4M ARR, and an 18-month runway. The growth had stalled. Sales cycles were too long, customers were churning at higher rates than the team had budgeted, and the venture investors were starting to ask uncomfortable questions about the path to Series A.
The founders were excellent. The product was solid. The market wasn't buying.
The engagement: 90 days to figure out whether this was a problem of execution (sales process, customer success, marketing) or a problem of positioning (wrong customer, wrong product, wrong market) — and to act accordingly.
Days 1-14: Discovery and the first surprise
I started with customer interviews. 12 conversations across the customer base — current customers, churned customers, lost prospects.
The pattern that emerged was unexpected. The current customers weren't buying the product the company thought they were selling. The marketing claimed "patient flow optimisation"; the actual usage was overwhelmingly around staff scheduling and shift management. The customers had bought the product because of one specific feature in the staff-scheduling area, and were tolerating the rest.
The founders were aware that staff scheduling was used heavily. They had not appreciated that it was the actual reason customers had bought.
Days 15-30: The hard conversation
The implication was uncomfortable. The company's positioning, marketing, sales pitch, and product roadmap were all built around patient flow. The actual market was buying staff scheduling. The two are adjacent but distinct.
The founders' first instinct was to reject the framing. They'd built the company around a specific vision; staff scheduling was a feature in service of that vision, not the product itself. The conversation in week 3 was tense. Two senior team members thought I was missing the bigger picture. The CEO eventually came around. Not all at once.
The work in this period was less analytical than relational. The framing had to land before any pivot work could happen. I should have anticipated this — pivots are emotional before they are strategic — but I underweighted it in the engagement plan.
Days 31-50: Repositioning
Once the team accepted the framing, the work moved quickly. We rebuilt:
- The website — repositioned around staff scheduling, with patient flow as a secondary capability
- The sales pitch — reframed around the buyer (operations directors and CNOs) who were actually purchasing
- The product roadmap — staff scheduling features promoted to the lead investment, patient flow features deferred
- The pricing — restructured to align with the staff-scheduling market's pricing norms, which were different from the patient-flow market's
None of this was rocket science. All of it required the team to fully accept the new framing. The framing acceptance was the gating step.
Days 51-70: Sales and customer success rebuilds
The new positioning required new sales motions. The buyer was different. The discovery questions were different. The reference customers needed reframing.
This was the slowest part of the engagement. The two account executives on the team had spent 18 months selling the old positioning. Switching their pitch was harder than expected — partial slips back to old language for weeks. We ran weekly call reviews with explicit attention to the language used. Improvement came, but slower than the timeline suggested.
The customer success rebuild was easier. The current customers were already using the product as staff-scheduling software; the customer success team just had to formalise what they were already doing.
Days 71-90: First validations
By day 75, the new positioning was producing different sales conversations. The pipeline metrics were noisy at this point — too few opportunities to draw conclusions from — but qualitative feedback from prospects was different. They were asking different questions. They were responding to the demo differently.
By day 85, the first new customer closed under the new positioning — a healthcare system buying primarily for staff scheduling, with patient flow as an "and we get this too" benefit. The deal cycle was 40% shorter than the previous average. The deal size was 15% larger.
One data point isn't a trend. But it was the kind of data point we'd been looking for, and the team's confidence in the new direction grew accordingly.
What worked
- Customer interviews early. The framing shift came from listening to customers, not from analytical work in PowerPoint. The first two weeks of interviews were the highest-leverage time of the entire engagement.
- Forcing the framing conversation explicitly. Once the team accepted the new framing, the rest of the work moved fast. The framing-acceptance work was the bottleneck.
- Rebuilding multiple workstreams in parallel. Marketing, sales, product, customer success, pricing — all needed to shift. Doing them in sequence would have taken six months. In parallel, ten weeks.
What didn't work
- Underestimating the emotional work. I went into the engagement assuming the framing conversation would take a meeting. It took weeks. I should have built that into the engagement plan.
- Trying to retrain the existing AEs. The two account executives had been selling the old pitch for 18 months. Switching them was harder than I anticipated. In retrospect, hiring one new AE who started fresh on the new positioning would have produced faster results than retraining.
- Insufficient communication with the board. The investors had been told the old story. Updating them on the pivot took longer and more careful work than I planned. I should have engaged the board chair as a partner in week 2, not week 8.
What I'd do differently
- Start customer interviews on day one, before any other work. They're the highest-leverage activity in any pivot engagement.
- Plan explicitly for the emotional and relational work of the pivot, not just the analytical work. Build it into the timeline.
- Engage the board earlier. Pivots without board alignment slow down at the worst possible moment.
- For sales motion changes, consider a fresh hire alongside retraining. The retraining cost is higher than typically estimated.
The longer outcome
I checked in with the company at six months and twelve months post-engagement. The new positioning held. ARR roughly doubled in the year after the pivot. Series A closed at the 14-month mark, ahead of the original runway estimate.
The pivot didn't guarantee any of this. Plenty of pivoted companies don't recover. What the pivot did was give the company a positioning that matched what the market was actually buying — which is necessary but not sufficient for the rest of the work.
The lesson that generalises
The most valuable thing the engagement did was force the team to listen to what their customers were actually saying — and to accept the implications. That's a generalisable lesson. Most stalled companies aren't stalled because of strategic mistakes. They're stalled because they're not yet listening to a signal their customers have been giving them, often for some time.
The job of the engagement, more often than not, is to make the listening unavoidable.
