Challenge
Product conversations often centered on usage, adoption, stickiness, or delight without clear linkage to commercial value. In practice, this meant we were not speaking the same money language as our commercial conterparts and delivery effort was not consistently constrained by potential return. We needed a practical way to bring commercial thinking into prioritisation and delivery decisions.
Approach
I introduced the concept organization-wide and led the full rollout:
- Defined Money Stories as a simple estimation method: use two known variables and estimate the third to create a first-year commercial impact range.
- Embedded Money Stories into the forming stage so PMs bring an initial story into the first shaping session.
- Operationalized the artifact across delivery updates and Product Syncs so commercial impact remains visible as bets evolve.
- Standardized format around hypothesis, formula, low/high range, assumptions, confidence notes, and exec summary.
- Added Money Story fields into ClickUp and the Shaped Bet template to make impact estimations trackable and reportable.
- Built a Signable-specific ChatGPT skill to coach, generate, and critique Money Stories for PMs.
ChatGPT Skill Contribution
The custom skill supports PMs in three modes:
- Coach mode: identifies the right story pattern and asks for only the missing inputs that materially affect the estimate.
- Generator mode: produces a first-year impact range, formula, assumptions, workings, and an exec-ready summary.
- Critic mode: challenges weak logic (false precision, double counting, wrong pattern choice, unnecessary complexity).
It uses six common Money Story patterns (upsell, volume, retention/churn, acquisition, market entry, cost saving) and intentionally pushes simple range-based estimates suitable for executive discussion.
Adoption and Change Management
Early adoption uncovered predictable misinterpretations: over-modeling too many variables, treating Money Stories as strict ROI accounting, and over-relying on tooling to "produce the answer." I addressed this by running a focused workshop with worked examples, reframing Money Stories as a decision and alignment tool rather than an accounting mechanism. This improved consistency in how PMs applied the method.
Impact (to date)
This is still an early rollout, but adoption and leadership response have been positive.
- Shifted shaping conversations toward explicit commercial hypotheses, not only product activity metrics.
- Increased leadership engagement and confidence in product bet discussions.
- Established a repeatable mechanism for tracking potential commercial impact across in-flight development work.
- Improved commercial fluency in the PM team, with stronger cross-functional dialogue with Sales, Marketing, and Customer Success.
What I'd Improve Next
- Start future rollouts with examples first, then framework, to reduce confusion early.
- Provide clearer guidance on data availability and acceptable estimation confidence by pattern.
- Further refine time-horizon handling where strategic bets may require payback periods beyond one year.