Featured deal · Fortune 50 financial services firm
25k → 250k

10× expansion in six months at a Fortune 50 firm — by giving them the visibility that unfroze stalled ERP decisions.

The account was sitting on a backlog of ERP buying decisions they couldn't make without insight into internal delivery. I positioned an Oracle project portfolio product as the visibility layer, landed a $25k proof phase in August, grew it +$100k by October, and added another +$100k in February. Then early-renewed and co-termed the whole contract to the ERP end date to lock expansion pricing. What follows is how it actually ran.

Quick facts
Company
Fortune 50 financial services
Product
Oracle project portfolio product
Cycle
Across two quarters
Outcome
10× expansion
The problem

Decision paralysis, dressed up as a project management problem.

The account had a live Oracle install and a growing appetite for new ERP capability. But every expansion conversation stalled in the same place: they couldn't tell me — or themselves — when their internal engineering team would be free to implement anything new.

Their engineers were spread across Jira and the existing Oracle project tooling with no uniform way to track hours. The project backlog was 50+ deep. Leadership had no view of when it would clear. That uncertainty had frozen every ERP buying decision on the table.

The pain wasn't the tooling. It was the decision paralysis the tooling was creating. Every conversation about new spend hit the same wall: we don't know what we can absorb.

The unlock

Not another PM tool. The visibility layer.

Every competitor in the room — including Jira with Tempo — was pitched as "better project management." That framing kept losing because the account didn't want more project management. They had project management. They wanted a way to score the backlog, tie hours to project value, and see what was worth doing next.

The Oracle product could license thousands of engineers individually, each tied to a unique HRIS ID that already existed in their ERP. That meant it didn't require a process change — engineers kept working in Jira for day-to-day PM. The product sat on top and turned all that activity into profitability data.

The reposition was simple: this isn't a PM upgrade. It's the visibility layer that unblocks every buying decision downstream of it. Once leadership saw it that way, the frame of the whole account shifted.

Sold the account on scoring engineering hours against project value — not on managing projects better. Different problem, different buyer, ten-times the deal.

The motion

Two champions. Two different problems. One story.

The technical champion was the Director of Systems. He knew the ERP footprint cold, but he couldn't get expansion decisions moving until someone could tell him what the engineering team could realistically absorb. He needed timelines and rough costing so he could sequence what to buy next.

The economic champion was the VP of Project Management. She owned the budget and signed off on expansions. What she needed was a way to rank internal projects, attach a cost to each, and put a timeline against them — so she could manage up to executive leadership with real numbers.

Neither of them could move the account alone. The Director knew what to buy. The VP had the budget to buy it. Once I connected the two conversations — his technical case + her budget and ROI story — the account started moving in weeks instead of quarters.

From there the sales motion was standard but disciplined: brought in the Oracle solutions team for a custom demo, ran a lightweight POC on their real project data, and wrote the internal business case for the VP to walk into procurement with. $25k proof phase in August. +$100k in October once the data was landing. Another +$100k in February.

The close

Procurement almost killed it. Here's how I saved it.

When the expansion hit procurement, they had one non-negotiable ask: early-renew and co-term every license contract to the ERP end date. Some of those contracts had 2+ years left. Others had 9 months. Procurement wanted a single co-terminated stack so they could manage the account as one line item going forward.

Internally this was a challenge. Co-terming meant giving up 12–18 months of renewal uplift revenue on the contracts that still had runway. That's real money to a sales org. Standard practice would be to say no and negotiate a different concession.

I made the internal case that the co-term was the price of admission on the expansion — that the upside on the multi-product growth story dwarfed the near-term uplift we'd give up on renewals. I ran the numbers: total contract value trajectory over 24 months with and without the co-term, projected expansion path across adjacent modules, and the strategic value of locking pricing at the current level before the next renewal cycle.

I got the internal approval. Procurement got the co-term they needed. The customer signed. Expansion pricing was locked to the ERP end date, which meant every future module conversation started from a position of strength.

Procurement asked for something the vendor didn't want to give. I built the internal case that made it worth doing anyway. That's what closed the deal.

What this deal shows

Four things this proves about how I sell.

01
Multi-thread selling into technical and executive buyers.
The deal didn't move until I connected the Director's technical case with the VP's budget and ROI story. Neither of them could sign alone. Both together were unstoppable.
02
Repositioning as the difference between a $25k deal and a $250k account.
Every other vendor was selling "better PM." I sold visibility that unfroze downstream decisions. Same product, different problem, ten-times the deal size.
03
Commercial creativity under procurement pressure.
Procurement asked for a co-term management didn't want to give. I built the internal case that made it worth giving. Expansion story beat renewal uplift on the numbers.
04
Land-and-expand as the primary motion.
$25k proof phase → $125k in three months → $250k in six. Multi-product expansion isn't the exception. It's the shape of every deal I try to run.
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