Sightglass Insight Series: Interview with Lindsay Jackson

John:

For this Sightglass Insight series, I’m joined by my friend and client, Lindsay Jackson. Lindsay has done something many people strive for in their careers—something that’s difficult enough once, but she’s about to do it twice.

She took a practiced craft and built a successful business around it. That alone is impressive. But now, she’s applying all of that experience, insight, and effort to build a second company—this time productizing her work into a technology platform. Lindsay founded LTJ Global, a renowned DEI consulting firm, and is now building a tech company grounded in everything she’s learned. Founding once is enough—but you’re doing it again.

Lindsay, can you tell us a bit about your background and how you came to the idea of turning this into a platform?

Lindsay:

It’s funny—my best friend, who I’ve known since I was 15, is giving birth right now as we’re speaking. It reminds me of something: the reason I had a second child is because I completely forgot what the first birthing experience was like. I think I’m seeing a pattern—maybe I’ve forgotten what it took to start a company the first time too!

My career has been a winding, often nonsensical road. Most people are surprised to learn I started very young—at four or five I knew I wanted to be a professional contemporary dancer. Or Janet Jackson’s backup dancer—same thing, right?

I took it seriously. I tested out of high school and started university at 15 so I could pursue dance full-time. By 20, I had my graduate degree. I studied, danced, and toured across continents, and conducted research into intersectional health modalities—work that felt fringe 20 years ago but now underpins real change in healthcare systems.

That journey—living and working across four continents—led to LTJ Global. I took what I learned from two prior companies, one in Australia and one in Ireland, and all that academic and artistic training, and channeled it into building a successful consulting business.

John:

And now you’re starting your second company—Sojourn DEI—as part of LTJ Global. It’s a totally different landscape than when you started the first. What has it been like navigating the tech startup world—fundraising, pre-sales, advisors, the whole thing?

Lindsay:

It’s kind of like having a second child. The first time, you’re so confident and judgmental—like, “I’d never let my kid do that.” Then the second time, it’s “Sure, have a cookie before bed.” We at LTJ thought we had learned so much, that we were prepared. But this has been a whole different beast.

That’s when I called you, basically crying, like “My baby’s broken!”

Client services is clear: you work an hour, you bill an hour. Tech? It’s a constant sprint. You’re always interrogating customer needs, evaluating what’s working in marketing, trying to stay ahead of the next six weeks. Add to that the sociopolitical environment we’re in—there was a time when we worried we couldn’t even say “DEI” out loud without legal implications.

There’ve been sleepless nights and tears, but that’s why partnerships like ours are vital. As a tech founder, you need someone you can call and cry to—someone who not only understands, but says, “I’ve seen this before. Here’s the path forward.”

That’s actually why we named the app Sojourn DEI. It’s all about small, intentional steps forward. One sojourn at a time.

John:

That really resonates. Our personal relationship—beyond the commercial one—has been essential to me too. As minority co-founders, those phone calls have been mutual.

You’ve now had so much experience doing this, and are in your second go-round with Sojourn. What advice would you give to other underrepresented founders who are just starting out?

Lindsay:

Just to clarify: when we talk about “minority founders,” we don’t mean ownership stakes. We’re talking about being members of historically and currently targeted populations.

If you’ve been watching the news—especially in the U.S.—you’ve seen rights being stripped away from LGBTQIA+ communities. We’re trying to grow companies and launch innovative products, but we’re also worried about our families, our partners walking down the street safely. That takes a toll.

There’s research to back it up—this emotional drain impacts our leadership, our teams, even our business outcomes. That’s why we need support structures that actually support.

One thing I’ve learned: not all help is good help. Just because someone offers assistance doesn’t mean they have your best interests at heart. After 20 years building businesses around the world, I’ve seen it again and again.

John:

Powerful. And it really ties into why you built Sojourn—there was a gap in the market. A lot of people wanted to do DEI work but couldn’t afford traditional consulting. So you turned all that expertise into an accessible SaaS platform.

Lindsay:

Exactly. We filled a room with chocolate and chips and asked: “What if we poured everything we do into a platform?” Something affordable that nonprofits and small businesses could actually use. And we tested it. We got out into the world, kissed babies, shook hands.

Still, we ran into advisors and VCs saying, “I don’t know if this DEI thing is going to stick.” Or, “What does the ‘E’ stand for?”

That’s when we got focused: we stopped chasing those people. We know there’s a sizable market, a desire to do this work, and a desire to fund it. That clarity helped get Sojourn to where it is today.

John:

It’s rare for a non-technical founder to build a tech product. What’s been the biggest surprise for you?

Lindsay:

Honestly? That good leadership finds a way.

No, I don’t have a technical background. But I have an amazing team. I trust them and they trust me. There’s no problem I don’t think we can solve together.

The gap wasn’t in passion or expertise—it was in translating ideas into wireframes. So we brought in Janine Spence, a brilliant tech synthesizer. She had the patience to sit with us, listen, and help shape our vision into a real product.

Too many non-technical founders get dismissed. But an engineering degree doesn’t make a product successful. It’s about pivoting, problem-solving, and being willing to say, “I don’t know—but I’ll find out.”

John:

That theme of relationships keeps coming up. You’ve clearly built something based on deep trust—with your team, your partners, your advisors.

Lindsay:

Absolutely. I believe we’re moving into a relationship economy. Maybe in 50 or 100 years, we won’t measure value with paper money, but with connection.

But people don’t know how to build relationships. They don’t know how to work across difference, or have healthy conflict. That’s going to be the dividing line between successful companies and the Kodaks of the world.

If you’re not teaching your team how to build inclusive, diverse, relationship-centered cultures, your company is at risk.

John:

So let’s close by talking about what excites you most about Sojourn DEI right now.

Lindsay:

First—people are still shocked by the price. $149/month. We did the research. We know what your budget is for people and culture development. We wanted to build something that a small nonprofit or midsize business could say “yes” to immediately.

But what I’m most excited about is our DEI Manager Button. One click, and you’re talking to a real expert. Need help with a tricky situation? Rolling out a training? Want advice on one of the tools? You’ve got support—real, immediate, expert support.

It’s delicious. You feel like you’re actually making a difference. That’s why we do this work. To create ripple effects for hundreds of people across an organization.

John:

Amazing. Thank you so much, Lindsay. It’s always a joy to talk with you. And thank you to everyone who joined us for this Sightglass Insight conversation.