Feb 7, 2023 · 31m · saastr
How To Adapt Your Sales Strategy To The Current Sales Environment | Modern Health SVP of Sales
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of CRO Confidential, host Sam Blonde and Modern Health SVP of Sales Hannah Wilson discuss how enterprise revenue leaders can adapt to macroeconomic headwinds by winning over CFO gatekeepers and optimizing sales team capacity. They deliver actionable frameworks on ROI-driven messaging, channel partnership leverage, and avoiding the destructive pitfalls of sales overhiring.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. How this is scored →
Jason as informed peer 6.0 Guest teaching 2.8 Guest disagreement 0.5 Jason pushing back 1.0
speaking balance: gold is Jason, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 7:38 Debunking the ROI spreadsheet myth
Hannah pushes back against conventional sales wisdom that CFOs simply want an ROI calculation, revealing that Modern Health's CFO pokes holes in ROI decks and looks for buyer conviction instead.
Hardest push from Jason ▶ 15:41 Host presses on cutting bottom performersSam directly reframes Hannah's diplomatic explanation of resource allocation into a sharper tactical reality: cutting the lowest performing AEs to fund partnerships and SDR pipelines.
Biggest teaching moment ▶ 8:10 Gong data validating 'We Believe' statementsHannah shares hard conversation data from Gong showing that using differentiated conviction statements doubled Modern Health's win rates compared to generic product pitches.
Jason holds their own ▶ 18:25 Zenefits 2015 scaling breakdownSam details the exact failure mode at Zenefits where aggressive headcount expansion cannibalized territory quality and collapsed rep quota attainment across the board.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Jason as informed peer | Guest teaching | Guest disagreement | Jason pushing back | Why |
|---|---|---|---|---|---|---|
| Shifting Macro Dynamics and the Rise of CFO Gatekeepers | 4 | 3 | 0 | 1 | Sam opens by setting the macro context of 2023 tech slowdowns and invites Hannah to explain frontline shifts at Modern Health. Hannah explains the shift from selling exclusively to Chief People Officers to navigating CFO and board-level budget gatekeepers. The dynamic is entirely collaborative and conversational. | |
| Reimagining Sales Messaging with ROI and 'We Believe' Statements | 6 | 4 | 1 | 1 | Hannah outlines how Modern Health evolved their messaging from soft retention benefits to hard ROI, and subsequently to 'We Believe' conviction statements after consulting their own internal CFO. Sam demonstrates strong peer expertise by synthesizing the points and sharing parallel operational practices from Brex and Zenefits. | |
| Strategic Sales Reallocation and Maximizing Account Executive Efficiency | 5 | 3 | 1 | 2 | Hannah explains shifting investment from raw AE headcount to partnership managers who drive predictable lead volume. Sam pushes with a pointed interpretation asking if this means trimming underperforming AEs to fund SDRs and channel roles, which Hannah broadens into overall efficiency gains. | |
| Zenefits Case Study: The Dilutive Risks of Sales Overhiring | 9 | 1 | 0 | 0 | Sam takes the lead with an in-depth case study of Zenefits in 2015, detailing how overhiring 90 reps per month diluted lead quality and decreased overall revenue. He lays out three specific operational criteria for sales hiring, which Hannah completely endorses. |
Statements from this episode (13)
Blond: Modern Health has surpassed $100M in ARR
“Today, Modern Health is north of a hundred million dollars in ARR.”
Blond: Modern Health is valued at over $1 billion
“The business is valued at over a billion dollars.”
Blond: Current challenging sales environment is a return to normal
“Well, my personal perspective on this, which is relatively aligned with Jason Lemkin's is we've sort of returned to normal. Normal is, is still much more challenging selling environment than we've experienced over the last two to three years.”
Wilson: Enterprise software purchasing decisions are shifting to CFOs and CEOs
“One thing that's been consistent, and I bet most sales leaders would agree with this, is that the buying decisions, which used to be with the functional lead, which in our case is the chief people officer, are now oftentimes getting pushed to the CFO, sometime…”
Hannah Wilson: Modern Health doubles win rates when AEs discuss ROI
“And actually we had a check in with our CSM at Gong the other day, and we were looking at some of the data. And what we saw was that if AEs are talking about money, if they're talking about ROI, We actually double our win rate”
Hannah Wilson: Modern Health doubles conversion using 'we believe' statements
“And, you know, the same conversation that we had with Gong last week, where we were looking at our conversion rates, we saw that when we use these, we believe statements and this approach to selling, we actually double our conversion rates as well.”
Sam Blond: B2B companies underutilize internal staff who match buyer personas
“It's almost universally true where the product that you are selling at your business, you have the buyer of that product internally... And so companies probably under leverage that internal resource around you know, what the buyer, if they are selling to this …”
Hannah Wilson: Modern Health froze AE hiring to boost existing rep productivity
“One of the things we're doing is we're not, even though we're scaling revenue significantly, we're not adding account executives. We're actually putting that revenue to areas to make our current account executives more productive.”
Blond: Zenefits generated less total revenue after massively overhiring sales reps
“And so the actual result of hiring a bunch more SDRs and AEs wasn't that we had incrementally more revenue, but sort of less efficient revenue on a per rep basis. We actually had less revenue. We closed less revenue by hiring all of these people because it was…”
Blond: Recent tech layoffs stem from dilutive sales overhiring hurting efficiency
“And I believe that that is what has happened with a lot of companies over the last couple of years where They have over hired and it has been dilutive to an existing successful team. The efficiency across the board has been diminished, and now we're seeing a b…”
Blond: Brex Generated About 50% of Closed Revenue via AE Outbound
“Brex, we set the expectation from a very early stage that you are Going to outbound and about 50% of our closed revenue was outbound AE.”
Wilson: AE Capacity Is Almost Never the Limiting Factor to Growth
“And I've almost, you know, even in really high growth environments, I've almost never seen AE capacity being the limiting factor to growth.”
Blond: Cutting Underperforming AEs Increases Total Revenue in Lead Shortages
“If you cut the bottom performing whatever percent of the AE team, what that means is you will give the limited number of opportunities that you do have to performers that have a higher conversion rate and actually convert more revenue or more sales with fewer …”