She left a restructuring desk on Wall Street to build Parallel - the first tech-forward special education company in America. The youngest of six kids who all learned differently, she made a bet that the rest of the field is still catching up to.
In December 2025, Parallel reported a number that makes school superintendents lean forward: 98% of its students met or exceeded their Individualized Education Program goals during the 2024-2025 year. More than seven in ten moved faster than expected.
That outcome data is the reason Valspring Capital led a $20 million Series B, and the reason Parallel is no longer a promising New York startup story. It is a working national system. Today the company delivers psychoeducational assessments, speech-language pathology, behavioral and mental health counseling, and specialized instruction to school districts across 25 states, serving more than 10,000 students. The founder running it grew up navigating learning differences herself, which is the whole point.
Diana Heldfond DiGia founded Parallel in 2021 on a simple, stubborn idea: that learning differences are not deficits to be hidden but parallel ways of thinking that deserve real support. The company name is the argument. So is the model - human clinicians first, with technology built to make their expert work reach further, not to replace it.
Parallel exists because I believe no child's future should depend on luck.
When the pandemic sent everyone home in 2020, Diana moved back into her family home and did the thing the moment forced on a lot of people: she asked what she actually wanted to do. Her answer pointed backward, to a classroom where she had once been the kid who could not keep up, and forward, to a platform that could lower the cost and raise the reach of the support that had changed her own trajectory.
She was one of six children, all of whom learned in their own way. Her family treated that as something to act on, not apologize for - testing early, finding specialists, building scaffolding. She has called herself one of the lucky ones, and she means it as an indictment. Luck should not be the variable that decides whether a child gets help.
Before Parallel, her resume read like a different person's. She studied Science, Technology and International Affairs at Georgetown's Walsh School of Foreign Service. She went into finance at PJT Partners, working on mergers and restructuring - the kind of high-pressure advisory work that teaches you how money and incentives actually move. She advised early-stage startups and nonprofits, including the Aspen Institute and the Stanford d.School, along the way.
Then she walked away from all of it to start a company in one of the least glamorous, most bureaucratically tangled corners of American life: school district special education, a system that moves more than $100 billion a year and still leaves millions of students underserved.
She likes to repeat a line from her grandfather: "Life is like walking in a forest; there are many paths. Once you choose one, give it your all." She chose special education and has not looked sideways since.
The thesis is in the brand. Learning differences are not a lesser track. They run alongside - parallel - and with the right support they arrive.
Technology should enhance clinical quality, not replace it.
Plenty of edtech promised to disrupt schools and then collided with reality. Parallel reads the reality differently. Special education is not a discretionary nice-to-have that gets cut when budgets tighten. It is federally mandated.
Georgetown, then M&A and restructuring at PJT Partners. Advisory roles with early-stage startups and nonprofits including the Aspen Institute and Stanford d.School.
Out of pandemic reflection comes a company built to make care for learning and thinking differences accessible and affordable for K-12 districts.
Capital arrives to expand the network of providers and the districts they reach.
Recognized in the Education category for the Class of 2024.
Valspring Capital leads, with Rethink Impact returning. Total funding reaches $48.9M. Yumin Choi joins the board. Outcomes data takes center stage.
Education, Class of 2024 - a nod to building in a sector most founders avoid.
A national footprint assembled district by district, not headline by headline.
Backers include Valspring Capital and Rethink Impact, betting on outcomes over optics.
The metric districts care about most, moving in the right direction.
Assessments, speech-language pathology, counseling, and specialized instruction, delivered virtually.
The next two years are about coverage - reaching students wherever they are.
I know firsthand what it is like to grow up with a learning difference.
She is a frequent voice at education and venture forums, from the ASU+GSV Summit to the U.S. Chamber Foundation's International Women's Day stage. The shortest path to understanding why districts sign on is to hear her make the case herself.
▶ Diana Heldfond - Forbes InterviewShe was one of the lucky ones. Parallel is the system she built so the next 10,000 students - and the 10,000 after that - will not have to be.