Jason Kirby: Hello everyone, welcome back to Fundraising Demystified. Today we have Diana Heldfond with us, founder and CEO of Parallel. Welcome to the show.

Diana Heldfond: Thanks Jason, excited to be here.

Jason Kirby: I'm excited to have you and I'm excited for you to get the opportunity to share your story as a solo founder raising more than $28 million. But before we go into all the details, I'd like you to introduce yourself, tell us a little bit about your story and what you're building at Parallel.

Diana Heldfond: Yeah, for sure. Well, to start, Parallel is a virtual care platform. We work with kids primarily who struggle with learning and thinking challenges—dyslexia, ADHD, speech impediments, really all kinds of mental health challenges. We work particularly within school districts across America. We're in about 15 states right now partnering with 80+ districts to ultimately plug into their special education departments and help them deliver services directly to the kids who qualify for them.

So we have a robust network of virtual providers who cover all different backgrounds—everything from specialized instructors to speech and language therapists, social workers, the list goes on and on. Ultimately, they plug in and work with these districts directly via our proprietary platform.

The platform itself is meant to aid schools and providers in getting the best care delivered and also the most efficient and effective care. It's been an exciting journey at the intersection of the healthcare world and the education world, so it has been a good learning experience in both.

Jason Kirby: Those are two very difficult sectors to succeed in and you chose to combine them together. It seems to be working out for you, but I'd love for you to share how you got to the point of conceptualizing the idea behind Parallel and then going about building that company.

Diana Heldfond: Totally. Well, the story is pretty personal. I grew up with learning and thinking challenges myself—diagnosed with dyslexia and ADHD when I was about seven years old, which is fairly unique. Most kids are diagnosed much later, if at all. And it is historically pretty hard to procure resources once even identification has been made.

I was a unique case in which I really reaped the benefits of early detection and early intervention. From a mission perspective I was excited to rethink how you could deliver care in new and innovative ways and recreate my reality for more kids across America, recognizing that is certainly not the norm today.

The idea of virtual care was super intriguing to me even prior to COVID—really increasing access, especially where there’s a shortage of highly trained, highly skilled providers. Putting things online is the only way to provide highly individualized resources for students. We're not talking about seventh‑grade math; we’re talking about small‑group reading intervention or one‑on‑one work to help overcome a very specific communication or articulation challenge.

To have that one‑on‑one individualized care at scale it had to be virtual if you're going to reach far‑flung, underserved communities. COVID exacerbated issues within school systems, specifically in special ed, but it also made people believe there was a real opportunity to put things online. Some companies had been doing virtual K‑12 therapy services, and they boomed during COVID, but many are essentially online staffing agencies. We came in as a tech‑enabled service provider focused on making care not just accessible to more kids, but actually exponentially better than in‑person.

With that comes tools for providers and tools for school districts to manage caseloads and track student outcomes so they can help students thrive, graduate out of special ed, make room for others who need support, and run a more productive, efficient department.

Jason Kirby: It sounds like timing worked out for you. It sounds like you launched this either during or right after COVID. Is that accurate?

Diana Heldfond: Right in the middle of COVID. I’d reached out to advisor types—my background’s not clinical; it’s on the business/finance side. Prior to COVID I started talking to clinicians to rationalize if online services were even viable. People laughed in my face. Six months later some of them reached back out saying, “Okay, I’m ready—let’s talk now.” By September 2020, we incorporated the company. 2021 was when things really started to pick up.

Jason Kirby: You did this by yourself. You're a solo founder—no CTO co‑founder. What made you jump in solo and what's that journey been like?

Diana Heldfond: I’ll say it’s still almost an experiment—I’ll report back in five years. A founder friend told me: don’t wait to find a co‑founder. You can always add one later, but you’ll stall progress trying to find the perfect match—especially a technical co‑founder for a niche, mission‑driven business.

So I jumped in, thinking maybe I’d find a co‑founder down the road. Once I stopped waiting, momentum picked up quickly. We built a robust group of clinical advisors to help with the first product and services prototype, and a small contractor team. As we kept adding people, we moved past the point of thinking about a co‑founder seat.

It takes a certain type of person to deal with startup highs and lows. The hardest part of not having a co‑founder is that when things get hard, it’s on me. On the brighter side, we raised money early, which let me hire great people and pay them well—no need to give a co‑founder title. Early employees got meaningful equity and a founder mindset. Today I have a robust exec team acting with a founder mentality despite no formal co‑founder.

Jason Kirby: You mentioned raising money early so you didn’t need co‑founders. How did you bring on those early resources? What did you validate to attract investors, and how did you access them?

Diana Heldfond: We raised our pre‑seed in the golden age (2021) when digital health was hot and COVID tailwinds were strong—so take my advice with a grain of salt.

Tactically, as I explored Parallel I tried to get investor buy‑in early. Anyone in my network who was an investor or knew investors—I took coffee chats to put the idea in front of them. I used those conversations both to develop my idea and to softly pitch. The trick wasn’t, “this is exactly what I’m building, what do you think?” but “you see a lot in this space—what do you think of these ideas, funding appetite, and long‑term considerations?” Coming from finance, my fear was not being able to fund the business.

Healthcare legal setup is complex and costly—I remember a $25K quote to establish the right structures—so we knew we’d have to raise. When I was ready, I called those same people: “today is the day.” That helped close friends‑and‑family and early angels, then leveraged those to get intros to funds. We set out to raise a $500K pre‑seed that quickly became a seed when institutions engaged. We had three term sheets and chose the best‑fit partner. Fundraising is a momentum game—use connections and keep the ball rolling.

Jason Kirby: Great advice: start early and build relationships. Don’t pitch to get money—ask for insights so you can come back with the metrics that matter.

Diana Heldfond: Exactly. You learn what metrics investors want to see, making it easier to come back when you’ve hit them. For each round I talk to friendly investors in our space to understand the market: what they’re seeing, valuation perspectives, where they’re deploying. Staying plugged in makes the actual raise much easier.

Jason Kirby: You’re still a solo founder and the master of fundraising. Did that create friction while scaling?

Diana Heldfond: Fundraising has been my domain. Our exec team is strong and understands that as a venture‑backed company, fundraising is part of the gig. Our Series A took months; when I’m engulfed in a raise, my team steps in—joining investor conversations and keeping the business moving. Many come from startup world and know the drill.

Jason Kirby: You raised Series A in 2022 and recently a Series A+—in a tough market. What changed, and why the A+?

Diana Heldfond: The market changed even during our A—from initial outreach to close. Angels who committed early pulled out by signing because conditions shifted. Diligence got deeper. Tiger led our A and did significant diligence, especially their healthcare team.

At seed you sell the idea and founder fit. At A you need data to back the story: team fit, revenue/traction, retention, TAM, and a big vision. You’re proving the model can scale. Our subsequent round with Rethink Impact was opportunistic—we wanted to partner with them; their founder Jenny Abramson joined our board. Again, the process was data‑driven and long‑term focused. If I could go back, I’d hire finance earlier. We brought in a VP Finance in early 2023 and built the team—having real finance support would have helped at A. Expectations have only increased.

Jason Kirby: What milestones did you use to keep investors engaged through volatile periods?

Diana Heldfond: Bookings and revenue were big. We’re a healthcare services company with SaaS‑like, minimum‑commitment contracts, so revenue/bookings are clear signals. We also time fundraises around the K‑12 cycle—Q4/Q1 is strong post‑renewals.

Being mission‑driven, we also highlight the number of students served. Team matters too—key hires (sales leader, operator, CTO) make outsized impacts. Product roadmap execution and, in our world, outcomes data: we collect and report on student improvement. For later stages we’re focused on retention/churn, top‑line growth, and burn multiple—cash spend matching growth.

Jason Kirby: As a solo founder, did you take investor meetings alone?

Diana Heldfond: I took first meetings alone. As we advanced, my COO joined many, and in the recent round our investor spoke with every exec individually. For a future Series B, my VP Finance is in most investor meetings. Over time you need data and storytellers from other teams—and it’s a great way to build investor confidence in the whole management team.

Jason Kirby: EdTech sales cycles are brutal, and you added healthcare complexity. What’s been your experience selling and scaling GTM?

Diana Heldfond: Many investors avoid K‑12. We’re different because services can move quickly—schools either need them or they don’t—versus ripping and replacing core systems like LMS or curriculum which can take years. K‑12 budgets typically open July–October, so many edtechs only sell in Q3. We can sell year‑round because demand for our people is constant, with peaks in Q3 and again Jan/Feb. Renewals start around now.

Our foot‑in‑the‑door is staffing gaps (e.g., posted openings for speech‑language therapists). As we deliver, we expand within districts with additional services and product features. Our cheapest growth is land‑and‑expand—making year one great and offloading more to Parallel in year two and beyond.

Jason Kirby: Let’s talk mistakes—what would you do differently in fundraising?

Diana Heldfond: Don’t wait to fundraise, but be mentally ready. I’ve taken calls when a fund wanted to preempt us and I wasn’t ready to pitch the big picture or how we’d use $15–20M. You’ll feel when momentum is there and you know exactly how you’d deploy capital.

During our A, I knew Jan 1 that we should raise, but I kept polishing the deck for two months. As a solo founder, sometimes you just have to go. Also, be prepared for rejection—it’s constant, even when things seem to be going well. Keep fundraising somewhat compartmentalized so the whole org isn’t emotionally tied to the round’s timeline.

Even with a banking background, telling the long‑term financial story is hard. If you’re not a finance‑focused founder, get help—advisors/consultants—to build a robust model before you launch the raise. It will save you from a thousand follow‑ups in the data room.

Jason Kirby: Can you quantify the grind—meetings and rejections?

Diana Heldfond: I’m a “tight process” person. At one point I took meetings with 40+ investors in a single week, across funds and angels. It’s a hustle even to generate enough interest to fill that calendar. Keep decks to ~12 slides focused on what matters and compress meetings into a short window.

Most of those 40 were no’s—but you only need one yes. The morning we got our Tiger term sheet I was at my wits’ end. Any little thing can derail a great pitch, so have a strong support system and expect the highs and lows.

Jason Kirby: What’s the best way for founders to learn more or connect?

Diana Heldfond: Parallel is at parallellearning.com. The best way to reach me is LinkedIn (Diana Heldfond). I’m happy to chat with founders going out to fundraise—if I’m slow to respond, apologies in advance!