What if the reason the world's biggest companies keep failing at AI has nothing to do with the AI itself?

Siobhan Savage is the co-founder and CEO of Reejig, the Work Operating System helping the most complex organizations on earth move work to worker in the age of AI. She works with Fortune 500 companies across banking, pharmaceutical, and retail, and she is building a billion-dollar company on a single conviction:

opportunity belongs to the builder, not the platform.

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HER STORY

One of twelve children. Canadian born, Irish raised, 15 years in Sydney, now in New York. She built her career in workforce strategy on multi billion dollar projects, obsessing over one question: how do you move work to the right worker and make a business run at high velocity?

She never imagined agents would become a form of worker. Now that future is arriving, and the Fortune 500 calls her to make sense of it.

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WHAT THIS EPISODE EXPOSES

In this episode of Truth Works, Jessica Neal and co-host Jeff Markowitz sit down with Siobhan to reveal what is really happening inside enterprise AI.

Most large companies have turned AI into transformation theatre: 12 month programs, enormous consulting bills, prompt training that changes nothing, and tools that get switched on then quietly switched off when the ROI never shows up.

The problem is not the technology. It is that almost no one has actually looked at how the work runs.

Reejig spent $40 million mapping how work actually works, building a view of tasks, subtasks, and skills before large language models were even real. That map is why Siobhan can walk into a company and understand 80% of its work without touching a single system.

She also draws a hard line on responsibility. Being Bold AND Responsible is not a slogan for her, and she refuses to design a world where two iPads interview each other in a boardroom.

Then it gets personal: raising "baby builders," the mom guilt of 16 hour days, and the human skills she believes will matter most in the careers of the future.

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TOPICS COVERED

THE BACKSTORY
→ One of twelve children, Canadian born, Irish raised, 15 years in Sydney
→ Starting out in workforce strategy and the obsession with moving work to worker
→ Recruiting as the ultimate training ground for resilience and connection

THE ENTERPRISE AI REALITY
→ The real reason enterprise AI is failing, and why it is not the AI
→ Transformation theatre: long programs, consulting bills, prompt training that changes nothing
→ Why tools get switched on then switched off when the ROI never appears
→ Making invisible work visible without plugging into emails or calendars
→ How Reejig spent $40 million mapping work before large language models were real
→ Understanding 80% of a company's work without touching a single system

VALUE OVER COST
→ The shift from cutting cost to unlocking value and growing margin
→ How an invoice that took five hours can be reduced to 45 minutes
→ Why your job is made of tasks, and how AI quietly removes parts of them
→ Emerging and declining skills, and the danger of "jobs of the future" courses
→ Stealth change management and the iPhone upgrade approach to adoption

THE BIGGER QUESTIONS
→ What it means to be Bold AND Responsible when jobs are on the line
→ The leaders harvesting people out of jobs while paying consultants millions
→ How the CHRO role is about to fundamentally change
→ Managing a workforce of both humans and agents
→ The handcrafted human experience making a comeback, even at AI companies

THE PERSONAL SIDE
→ Raising "baby builders" and teaching kids to use AI early
→ Why human to human skills become more valuable, not less
→ Mom guilt, 16 hour days, and choosing to build
→ Why opportunity belongs to the builder, Jane in accounts, not just the PhDs

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This is a conversation for anyone trying to understand what work becomes next, whether you lead a Fortune 500 company or you are figuring out your own place in the AI era.

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Guest: Siobhan Savage, co-founder and CEO of Reejig
Hosts: Jessica Neal and Jeff Markowitz

Three friends. One closet. A company now valued at $10 billion, serving over 400,000 small businesses.

Josh Reeves is the co-founder and CEO of Gusto, the payroll, benefits, and HR platform now valued at roughly $10 billion. But he didn't grow up dreaming of building HR software — nobody does. The son of two teachers who were the first in their families to go to college, Josh studied electrical engineering at Stanford during the dot-com collapse, when the conventional wisdom was that the internet was finished. He ignored it. After a stint as a product manager at Zazzle and a first startup he now describes as "stealth mode" — his polite way of saying he had no idea what he was doing — Josh walked away with the most important lesson of his career: never start a company just because your friends are.

In 2011, he and two co-founders started Gusto to fix something genuinely broken. Payroll, benefits, and the systems that quietly reduce people to ID numbers and acronyms — especially in small businesses, where two-thirds of U.S. employers have fewer than five people and every hire is a real human being, not a line item. They set one rule: they wouldn't pay themselves until they could do it through their own product. They launched in December 2012 with 100 small businesses. One co-founder spent four months sleeping on an air mattress in a roommate's closet — it had a skylight, for the record, and the roommate's clothes were still hanging inside.

Fourteen years later, Gusto has grown from three people in a Palo Alto house to over 3,000 employees ("Gusties") across Denver, San Francisco, New York, and Scottsdale — with no headquarters, by design. In this episode, Josh sits down with Jessica to unpack how he protected culture at scale, why he deliberately left revenue on the table to launch in all 50 states the right way, and the framework he uses to resist Silicon Valley's growth-at-all-costs gospel.

You'll learn:
- Why second-time founders have an edge — and why Josh had role, responsibility, and ownership conversations on day one
- The weekly feedback walks the three founders started when they were just three people, and still do 14 years in: three things working, three things to improve
- Why most systems treat people like transactions — and what changes when you build for the human moments instead
- The values-and-motivation interview Gusto uses to hire for what makes someone tick, not just what's on their résumé
- Why interviewing is a skill every leader should practice obsessively — and how the best interviewers dig past the first and second answer to what's really underneath
- How to scale culture without freezing it: "we're not a museum" — what should persist, and what should always be allowed to change
- The "no headquarters" home-base model, and why Josh personally interviewed Denver's first 10-15 hires to make it as important as San Francisco
- Why "doing things that don't scale" early can build the momentum that scales later
- Why he deliberately left revenue on the table to cover all 50 states comprehensively, instead of launching half-built
- The three checks-and-balances Josh runs against growth: product quality and compliance accuracy, unit economics, and team retention
- Why there are over 10,000 payroll rules in the U.S. — and why the business owner should never have to become the expert
- How AI is a tailwind, not a threat — making Gusto more of a teammate and partner to the small business owner
- Why work should be more than a paycheck: purpose, community, and impact, when the alignment is there
- The thought experiment every founder should run before committing: the 10,000th time you describe your idea, will you still be excited?

Whether you're starting a company, scaling one, or just trying to do work that means something, Josh's philosophy is the throughline — the one he repeats to his four kids and to every founder who'll listen:

In our family, we do hard things.

Truth Works is hosted by Jessica Neal, former Chief Talent Officer at Netflix, now in the business of telling the truth about how work really works.

At 11 years old, Dan Mishin convinced his grandmother to move in with his parents so he could turn her apartment into a backpacker hostel. The idea came to him in Berlin, where his mom's wallet had just been stolen and they were stranded overnight in a hostel full of laughing 20-year-olds speaking a language he didn't understand. He made two decisions on the train ride home: learn English, and open a place just like it.

That summer project became the largest hostel chain in Eastern Europe — 13 countries, 3,500 guests a night — and the start of one of the most unlikely founder journeys you'll hear this year.

In this episode, Dan sits down with Jessica Neal to walk through all of it. Starting a company at 11 in post-Soviet Ukraine, a place he describes as the Wild West, with no functioning law enforcement and entire generations of savings wiped out overnight by government decisions. Sleeping in his car for six months when the business almost went bankrupt. Signing 100-year leases with personal guarantees at 18 because Ukrainian law had no concept of bankruptcy protection. Raising a $100M term sheet that same year. Buying a yellow Porsche he now calls a total douchebag move. Ballooning to 280 pounds on a diet of Snickers and Red Bull. And eventually getting on a flight to the US with a single phone number — only to walk away from a 10-minute call with a $100K check at a $5M valuation.

After building Joon Homes to $300M and 250 employees, Dan hit a wall most founders don't talk about: he was building something valuable, but he didn't believe in it anymore. So he walked away to start Manifest — an AI-native legal company that's raised $60M to fix one of the most broken industries in America. The US has 1.3 million lawyers, ten times more per capita than most countries in the world, yet 80% of Americans can't afford one. Dan thinks he knows why, and he's rebuilding the entire system starting with immigration.

The conversation also goes deep on what it actually means to run an AI-native company — how Dan hires, why he believes generalists are winning, the applied AI engineers he embeds in every team, and the one-year severance policy he introduced to take the fear out of automating yourself out of a job.

A conversation about volatility, reinvention, and what it actually takes to build something that matters.

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📌 TOPICS COVERED

▸ Growing up in post-Soviet Crimea and the night in Berlin that started it all
▸ Convincing his grandmother to give up her apartment so he could open a hostel at 11
▸ Building the largest hostel chain in Eastern Europe as a teenager
▸ What it's like to sign 100-year leases at 18 with no bankruptcy protection
▸ Sleeping in his car for 6 months before raising $100M
▸ The yellow Porsche, 280 pounds, and the Snickers-and-Red-Bull years
▸ Landing in the US with one phone number and walking away with a $100K check
▸ Scaling Joon Homes to $300M and 250 employees
▸ Why he walked away from a high-growth business to start Manifest
▸ Why the US has 1.3M lawyers but 80% of Americans can't afford one
▸ How Manifest is rebuilding immigration law with AI from the ground up
▸ Why immigration is a hiring and retention lever most companies underuse
▸ Running an AI-native company: hiring, autonomy, applied AI engineers
▸ Why generalists are beating specialists in the AI era
▸ The 1-year severance policy that made AI adoption psychologically safe
▸ What to do when senior leaders refuse to adapt to AI
▸ His advice to over-thinking founders who won't take real risk
▸ Why this is the most exciting time in history to be building