This newsletter covers the business side of the education industry - venture funding, M&A, other financial transactions. Whiteboard Advisors also publishes a daily newsletter - What We’re Reading - of curated, industry-focused news clips and a weekly newsletter - Whiteboard Notes - which covers policy, industry trends, and insights from W/A CEO Ben Wallerstein.

Hello!

Looking forward to seeing many of you at EdTech Week October 13-15. If you’ll be in NYC that week, drop me a line so we can meet up in person!

Also apropos of EdTech Week, there is a limited amount of time left to apply for the Emerging EdTech Awards, designed for startups with $2-10M in revenue.

It is a deal-heavy edition today, here are the headlines:

With that, on to the news!

Whiteboard Advisors not only provides policy and market-related diligence and advisory services, we track every financial transaction that happens in education — and keep a record of all deals that are publicly announced. You can check out our Deals Database here:

The following transactions caught our eye over the past few weeks. If you have a deal to announce in this newsletter, please reach out.

Horowitz Andreessen Academy raises $42M / United States, Postsecondary Alternative / Andreessen Horowitz (lead), Angels

Andreessen Horowitz is backing a new postsecondary institution led by Udemy and Maven co-founder Gagan Biyani. Horowitz Andreessen Academy (h16n, if you will) has received mostly praise from the tech world and skepticism from those inside education. I’m somewhere in the middle, excited by the premise of college focused on teaching agency to young people but wary of educational institutions trying to scale on a venture timeline – see also, this week’s New York Times exposé of one of last generation’s venture darlings, Guidepost Montessori.

Jack & Jill raises $40M / United Kingdom, Recruiting Platform / Air Street Capital (lead), Madrona, Creandum, Entrepreneurs First, Ada Ventures, Expedite Capital, Repeat.vc

Jack & Jill raised its $20M seed last October; eleven months later, 380,000 job seekers use "Jack," its candidate-side assistant, 5,000+ employers hire through employer-side assistant "Jill," and revenue is up 40x. The model skips applications entirely — an introduction happens only when both the candidate and the employer opt in. 

Loora raises $22M / Israel, English Language Learning / Union Tech Ventures (lead), vgames, Emerge, Hearst Ventures, QP Ventures

Loora sells conversational English practice to adults, most of whom are learning for career advancement. With large established markets in Mexico, Japan, Germany, and Brazil, the company reports ARR "in the tens of millions" that has more than doubled over the past year on the back of a rapidly growing B2B sales motion. 

BoomerangHR raises $12.7M / United States, HR Software / Kalos Ventures and Album Ventures (co-leads), Monta Vista Capital, Capital Eleven, Strada Education Foundation, Atlanta Seed

BoomerangHR automates off-boarding — COBRA, equipment returns, exit interviews, non-compete monitoring — and runs company alumni networks for rehiring (returning employees now account for roughly one-third of new hires), referrals, and business development leads.

Aristotle raises $5M / United States, Online Tutoring / True Ventures (lead), Wicklow Capital

Aristotle sells voice-based tutoring for 13-to-18-year-olds in STEM, test prep and languages directly to families. It is early days for the company, but one way the product stands out is its voice-first approach. Using voice as a primary driver for digital interactions has spread like wildfire among software developers this year, but remains broadly underutilized and feels particularly relevant for tutoring.

AcademyAI raises $2.2M / United Kingdom, Workforce Skills Assessment / Nexus Family Office, Panthera Family Office

AcademyAI educates and trains employees on how to use AI in the workplace. The company does this through a mix of employer-sponsored bootcamps and short-form content programs. Co-founders Alex Packham and Andy Lambert previously built ContentCal, which was acquired by Adobe. The proceeds from this round will fund product development.

GoSprout raises $1.2M / United States, Apprenticeship Management Software / Education Innovation Ventures, Robin Hood, LearnLaunch, Bravo Family Foundation

GoSprout manages the back-office function of apprenticeship programs – tracking apprentice hours, competencies and employer compliance – and has now digitized 500,000+ training records. Of particular note, the company was selected as the technology vendor for Jobs for the Future’s “Apprenticeships Unlocked” program.

Perdoceo acquires South University / United States, Degree Provider

Perdoceo, owner of Colorado Technical University and American InterContinental University, will pay $130-140M (with another $74M in earn-outs and deferred payments) for South University, a university which brought in ~$291M in revenue and $34M in operating income in 2025. The deal returns South University to for-profit ownership nearly a decade after EDMC sold it to the nonprofit Dream Center Foundation. Closing is expected in 2027, pending regulatory and accreditor approval. 

Phoenix Education Partners acquires Fuel50 for ~$31.5M / United States / New Zealand, Career Pathing Software

The University of Phoenix parent is paying ~$31.5M in cash, plus up to $8.5M in earn-outs through 2027, for Fuel50, which maps employees' skills to internal roles and development paths for large enterprises. Fuel50 will operate as a separately branded subsidiary and be led by co-founder Jo Mills.

Pearson acquires ITS / United States, Assessment Delivery

Pearson is buying Baltimore-based ITS, which handles test delivery, remote proctoring and score reporting for credentialing programs — and which Pearson has been a customer of since 2009. ITS folds into Pearson Professional Assessments, the latest move in an assessment market that has been filled with transaction activity this year.

McGraw Hill acquires TeachFX / United States, Instructional Coaching Software

TeachFX records classroom audio and gives teachers feedback on their questioning and on how much of the talking students do, then aggregates the patterns for administrators. It is McGraw Hill's second acquisition of September, after Teachally, and extends a run of K12 professional development (PD) deals this year. See my interview with BetterLesson Learning CEO Robin Gonzales below for more on the state of the K12 PD market.

ESS acquires HeyTutor / United States, K12 Tutoring

ESS, the Vistria-backed K12 staffing company that places substitutes, paraprofessionals and clinicians in 1,200+ districts, is adding HeyTutor's in-person high-dosage and bilingual tutoring, which served ~8,600 students in math and ELA last school year.

Procare Solutions acquires Playground / United States, Child Care Management Software

Procare, a software platform powering 40,000+ child care centers, is buying Playground, an early-stage competitor that raised $3M in 2024 and has already grown to manage 5,000+ programs.

Pathlight Learning acquires four Primrose Schools / United States, Early Childhood Education

Pathlight, a Primrose franchisee recapitalized by Taurus Capital Partners in 2025, is adding four Omaha-based schools to its portfolio. The company also announced that it would start breaking ground on 11 additional schools in 2027.

Stepful acquires St. Louis College of Health Careers / United States, Healthcare Workforce Training

Three months after announcing its $55M Series C, Stepful disclosed that it bought the 45-year-old St. Louis College of Health Careers (SLCHC), now Stepful College, last December. Stepful plans to scale SLCHC's existing, accredited degree programs in nursing and respiratory therapy as well as launch new ones, adding further accelerant to one of the fastest-growing businesses in education.

Ascend Learning acquires M7 Health / United States, Healthcare Workforce Scheduling

Ascend, the Blackstone-backed healthcare education company that bought nursing school software provider TAMS in August, is adding M7 Health, which forecasts staffing demand and builds nurse schedules for health systems. In the words of Ascend CEO Lissy Hu, Ascend’s goal is to “[reach] healthcare professionals through their schooling, credentialing, ongoing upskilling and now their day-to-day work.” 

Wooclap acquires Vevox / Belgium / United Kingdom, Classroom Engagement Software

Wooclap, which raised $29M last year, makes its first acquisition in UK rival Vevox. Together, the two active learning platforms will serve 1,000+ universities and corporate training teams, including Duke, Durham, Deloitte, BP, and the NHS. 

Spaggiari acquires ESDS / Italy, K12 School Management Software

Ambienta-backed Spaggiari, a supplier of gradebook and school management software to Italian schools, is making its first acquisition outside Italy. ESDS runs student information systems and a project-based learning product across 3,000+ schools and 1.5M students, giving Spaggiari a foothold in Iberia and Latin America.

360training acquires Atlantic Training / United States, Compliance Training

Just a month after announcing their acquisition of eMedCert, 360training will add Atlantic Training's workplace-safety and HR compliance courses along with its environmental health and safety management software.

Main Capital Partners acquires Watermark Insights / Netherlands / United States, HED Assessment & Accreditation Software

Watermark sells accreditation, faculty review and student success reporting software to ~1,500 colleges and universities. Main, a Dutch buyout firm, noted that regulatory requirements drive demand for Watermark's software and make the segment attractive, though it is unclear whether the Education Department's proposed overhaul of accreditation requirements and accreditor responsibilities will expand or erode that demand.

Brighteye announces $72M first close of Fund III / Europe, Venture Fund

Europe's most active dedicated education venture firm reached a €62.4M ($72M) first close against a €100M target, with LPs including the Lumina Foundation, Zanichelli Ventures and PI Impact alongside the European Investment Fund and the Jacobs Foundation. Fund III also includes a rebrand of Brighteye’s thesis from EdTech to "HumanOS" — a logical broadening that echoes Reach Capital's Fund V. 

Gates Foundation commits $400M to AI in education / United States, Philanthropy

The $400M is 40% of a new, $1B commitment announced by the foundation. It will be earmarked for tutoring and teaching tools in US and international classrooms, plus independent evaluation. It follows the foundation's announcement of a career-readiness-centered US strategy and its $200M partnership with Anthropic in May.

Trott Family Philanthropies commits $100M to the University of Chicago / United States, Philanthropy

The gift anchors a $300M, ten-year Trott Center for Excellence in Rural America to recruit and support rural and small-town students from college preparation through job placement.

A conversation with Robin Gonzales on her path from the classroom to industry, CSA Education’s acquisition of BetterLesson, and her plans as CEO of the newly formed entity, BetterLesson Learning.

Looking for your next opportunity in education? Check out our W/A Jobs, which features 3,734 career opportunities from 331 organizations across the education industry. Hiring? For $250/month or $1,000/year, organizations can post an unlimited number of jobs with no per-job fees. A few roles that we’re excited about from the past week:

Whiteboard Advisors is the leading policy-related diligence partner for education investors, advising on most major private equity transactions in education over the past 15 years. Our specialty is translating complex policy dynamics into insights that inform decision-making. Reply to this email to learn more.