PROJECT 02 · VENTURE STRATEGY

Turning a 2030 vision into a venture roadmap

Three working sessions with Caterpillar's leadership in fall 2025 to decide where new ventures could move them toward their 2030 goals, and how to get there.

CLIENT
Caterpillar
CONTEXT
With UpLabs, fall 2025
MY ROLE
Strategic design lead. Designed all three sessions.
IN THE ROOM
20 executives, with a team of 8 venture builders and leaders I managed
THE ASK

Caterpillar already had a clear vision for 2030. Its leaders wanted to find where new ventures could get them there faster, and to agree on where to start.

I designed a three-part program that moved a large group from many possible problem spaces to a shared North Star, a roadmap, and the first bets.

THE PROGRAM

Three sessions, each with a clear outcome

1SEPTEMBER

Scoping

  • A survey of leaders to align on problem spaces
  • Prioritization exercises
  • Context captured for each problem space
OUTCOMECritical inputs to prioritize and sequence the work
2OCTOBER

Prioritization

  • Prioritized and sequenced problem spaces shared back
  • A review of the data foundation needed to move fast
  • The group refined its North Star and the KPIs it affects
OUTCOMEPrioritized problem spaces and alignment on the North Star
3NOVEMBER

Backcasting kickoff

  • A full-day backcasting workshop on the top problem spaces
  • Alignment on key stakeholders for field research
  • A plan for interviews and follow-on workshops
OUTCOMEAgreement on the North Star, the steps to get there, and who to involve
HOW WE CHOSE

Four lenses to find the spaces ready for venture building

DesirabilityIs this need felt across the industry?
ViabilityIs the market large enough, and how mature are current solutions?
FeasibilityCan it be built, on a timeline that fits the model?
Strategic fitIs there a clear right to win, and does it speed up the 2030 goals?
Strong area for venture building
Potential for high-impact point solutions
Recommend deprioritizing
THE BACKCASTING DAY

From the North Star back to a first move

Executives worked in pods through two rounds. Each pod described the future it wanted, named what had to be true, mapped four big steps back to today, and defined a first proof of concept and what to validate. The day ended with each pod presenting and the group ranking options by impact, feasibility, and momentum.

See the backcasting method →
Caterpillar executives during the backcasting share-out
Pods present their backcast to the full group
The working team with a vintage Caterpillar Twenty tractor
Part of the team, with a Caterpillar Twenty from the company's early years
Dusk over the water outside the workshop venue
End of the backcasting day
OUTCOME

What leadership left with

Clear prioritiesA ranked, sequenced set of problem spaces to pursue.
A shared North StarAgreement on the future and the KPIs that show it is arriving.
RoadmapsFour-step backcast paths from proof of concept to scale.
Next stepsFirst proofs of concept, validation priorities, and the stakeholders to interview next.

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