Jessie Woolley-Wilson

Operating Partner, Owl Ventures · 1 appearance on the record.

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She served as President and CEO of adaptive EdTech platform DreamBox Learning from 2010 through its 2023 sale to Discovery Education. Prior to DreamBox, she held executive leadership positions at Blackboard's K–12 Group, LeapFrog SchoolHouse, and Kaplan.

12statements → 5claims → 1claims resolved → 4/5average certainty → 1.67/5average debate potential → ≈4.5/5argument clarity, estimated →

1 supported 0 partly supported 0 contradicted 4 not checkable as stated how the 5 claims stand · each chip opens the sources

1 prediction · 4 assertions · 1 opinion · 4 insights · 2 disclosures · every statement was checked. The prediction and assertions are the 5 claims: statements the public record can support or contradict. 1 is resolved, and 4 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Jessie argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported

Woolley-Wilson: Almost 90% of kids have broadband and device access

“Now the good news is that almost 90% of kids have access to broadband and devices, but that doesn't help the 10% that doesn't.”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 9:48 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

How they sound: not measured why? →

We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of Jessie Woolley-Wilson on measured tape to publish a rate. This says nothing about how they speak.

What they said12 Episodes1

Everything Jessie Woolley-Wilson said on How I Built This that made the record, most notable first. Filter by type, assessment or year in the ledger →

Opinion

Woolley-Wilson: Only 10% of school districts are ready for hybrid reopening

“A month ago, I probably would have anticipated that 50% of the districts Will be returning in some hybrid model. I think that number is closer to 10% now. And so I feel right now we're in a pause and I feel like the next window is really after January to see h…”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 13:21 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Insight

Woolley-Wilson: Adaptive tech personalizes instruction at scale better than human teachers

“That's very difficult for even the best teacher in the best resourced school to be able to personalize learning instantaneously for 30 kids at once. But the nimble personalized learning technologies can do that very effectively at scale.”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 15:38 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Insight

Woolley-Wilson: Edtech should assist teachers' personalization, not replace them

“We think technology should do what technology does best, which is to help understand the thinking process of children and to give them actionable insights so that they can modify their instructional strategy and personalize it to be more high impact for every …”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 7:55 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Assertion Supported

Woolley-Wilson: Almost 90% of kids have broadband and device access

“Now the good news is that almost 90% of kids have access to broadband and devices, but that doesn't help the 10% that doesn't.”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 9:48 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Prediction Not checkable as stated

Woolley-Wilson: Edtech will see sustained post-pandemic growth as a must-have

“We really feel like education technology is a V-shape, and we're seeing that now. We've had explosive growth in users, as I mentioned, and we expect that that is going to continue for the future, because we feel like people who were trying out learning technol…”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 11:34 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Insight

Woolley-Wilson: Prioritizing staff over immediate revenue ultimately protects the business

“And we figured if we took care of our staff, then we could take care of our customers. And then the third piece was, if we take care of our customers, then we will take care of our company. So the default was not, what do we do to take care of revenue? The def…”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 1:35 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Assertion Not checkable as stated

Woolley-Wilson: DreamBox added over 2 million students in five weeks

“And within six weeks, we nearly doubled the number of students and districts were really desperate. So fifth In five weeks. So that was over two million students that were added.”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 3:31 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Assertion Not checkable as stated

Woolley-Wilson: Over 5 million K-8 students use DreamBox through schools

“So over five million. Students K through eight are using Dreambox through our schools.”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 3:50 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Disclosure

Woolley-Wilson: DreamBox moved staff to four-day workweeks during early pandemic

“Earlier, as part of our cost reduction, we moved everybody to a four-day workweek.”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 4:37 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Assertion Not checkable as stated

Woolley-Wilson: 40% of DreamBox employees are former educators

“40% of the employees at Dreambox are former educators.”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 7:47 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Disclosure

Woolley-Wilson: DreamBox shifted to institutional sales to reach all children

“So one of the reasons we moved from the consumer approach to the institutional approach is to bring Dreambox to every child. We brought Dreambox to where all kids were in schools. Not just to the parents who happen to know about it, but to institutions and com…”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 9:02 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Insight

Woolley-Wilson: 'Benevolent friction' means being hard on ideas, soft on people

“So benevolent friction is trying to capture the importance of Courageous conversations. We want to be hard on ideas, but soft on people.”

Jessie Woolley-Wilson Aug 8, 2020 ▶ 18:18 How I Built Resilience: Jessie Woolley-Wilson of DreamBox

Appearances (1)

Episode	Date	Speaking time
How I Built Resilience: Jessie Woolley-Wilson of DreamBox	Aug 8, 2020	13m

Jessie Woolley-Wilson

The record, in short

Their most notable supported claim

How they sound: not measured why? →

Appearances (1)

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