Greg’s a Senior Enterprise AE at a company called Upwards. Which is on a mission to ‘‘solve care for good,” by creating childcare solutions with enterprise companies for their workforce.
They’ve got a lot going for them:
- Childcare is shifting from a nice-to-have to a standard benefit to drive talent retention.
- Only 7% of companies have a care benefit, but up to 48% are looking for one.
That’s a huge gap. It’s Greg’s job to help close it by educating buying teams on the root causes behind the problem they’re trying to solve, while driving alignment on a solution.
Here’s an example:
Last year, a major enterprise’s Benefits team (part of HR) responded to an outbound campaign, looking to learn more about childcare as an employee benefit.
They talked through what other benefits teams are doing, he educated them on changes in the talent market, and they started to setup for the next benefits election cycle.
But then? The prospect went dark. Ghosted, after 400 days of planning.
How to take a different approach when you can’t win on a spreadsheet.
Before we get into how Greg went from ghosted to six figures, let’s talk about his approach to selling.
Most HR teams evaluate healthcare benefits in a spreadsheet. They list out all options, then make all the incumbents answer every question “RFP style.”
But Greg knows they’ll never win in a traditional RFP-style healthcare deal, because their model is too different. They’ll miss the mark on paper, if you’re using the typical benefits buying criteria.
Which means Greg needed to develop an entirely different approach.
Selling with champions, by selling with business cases.
Greg believes “anytime there's a price involved, you have to have value.”
The approach he uses to build “value” in his deals is a business case: a page or two page write-up with context on the problem, solution, outcome metrics and the investment.
Plus, Greg builds out a matrix that ties together:
- A quarter-by-quarter rollout plan.
- Expected outcome metrics.
- Required investment.
- Cost of no action.
In one simple table.
Creating an unlikely champion.
Back to that deal:
A complex sales cycle that had started 400 days earlier had gone cold. The deal had stalled out with the HR team, but then?
Somebody on the Employee Resource Group (ERG) reached out to Greg. Which is a separate team in the Enterprise focused on Diversity, Equity, Inclusion (DEI) — who aren’t specialists in or typically responsible for benefits.
While the Benefits team doesn’t always hear directly from frontline staff, the ERG often does collect data with feedback from the frontlines.
And can you guess who raised their hand to advocate for Upwards with Greg?
A software engineer.
Which is kind of like a product designer deciding to champion the purchase of account software. Usually, it just doesn’t happen like that.
Enabling Greg’s new champion to sell internally.
We all know it’s great to work with a champion who’s gotten deals done before. But in this case, Greg’s champion had genuine passion, but no true buying experience:
“This guy spoke from the heart, and he just knew this was needed, and that came across. So I had to train him on what to say, and how to bring this to his President in a way that would resonate with an executive.”
That’s when the deal started to pick up again by co-creating a business case together:
“He’d go do a little bit of research for me, he’d come back with some new inputs, then we would collaborate on the storyline and develop the message together.”
Turns out, Greg’s new champion was able to land time on their President’s calendar to pitch the value of a new program like childcare.
The place where Greg’s champion would share the 2-page executive summary they wrote out, scripting his message for the President.
So on one hand, the HR benefit team said “I don't think it's a problem. Not only that, I don't know if this is the right solution.” On the other hand, I knew my champion was meeting with their President to share the message we built.
Did you catch that?
Greg’s typical “buyer,” with all the experience and authority and responsibility for HR Benefits, started blocking the deal. Meanwhile, the least-expected type of role in the enterprise — a software engineer — had the ear of their President.
So Greg’s business case was designed to have the President looking at his HR team, thinking, “Well, all our frontline people are telling me this is a big problem, regardless of what you in HR are saying, and I’m going to do something about it.”
Which is exactly how the deal ended up getting done.
And in a truly dramatic fashion, HR showed up to that meeting that Greg’s champion had scheduled with their President!
By the time they left the meeting, their President had given HR a new mandate:
“He told them, ‘We’re doing this.’ So the following week, the HR Benefits team reached out, ready to start talking about a contract. Which only happened because that one meeting, with a strong message and an unlikely champion, turned our deal into a mandate.”
So, in short, Greg…
- Developed an unlikely champion.
- Co-created a strong business case.
- Enabled his champion to sell his President.
- Influenced the decision maker — even with a group of detractors in the room.
…which resulted in a $150K deal for Upwards, and access to childcare for frontline workers.
