Leading people in a tech powered workplace with Anthony Presley and Jason E. Brooks

00:05 – Jason E. Brooks:
Welcome to The Leadership Table, where conversations inspire, lead, and elevate. I’m your host, Jason E. Brooks, bringing real stories and strategies from leaders redefining how we lead in hospitality and beyond. Today I’m joined by Anthony Presley, CEO of TimeForge, a workforce management platform that helps operators tackle tough challenges from labor forecasting and compliance to team culture and leadership accountability. Anthony’s journey began in technology at an early age, then connected with hospitality, giving him a unique perspective on leading people in a tech-powered workplace. Under his leadership, TimeForge expanded from gig worker coverage to AI-powered forecasting while staying focused on people-first operations.

01:08 – Jason E. Brooks:
Before we dive in, subscribe so you never miss an episode that helps you lead stronger, scale smarter, and build the kind of team your guests never forget. Mr. Presley, you didn’t start in a tech company — you’ve been on the front lines of hospitality. Walk us through your journey from operations to leading TimeForge, and how that shapes the way you serve operators today.

01:53 – Anthony Presley:
Happy to. My path isn’t traditional. I actually started on the tech side in middle school. My father was stationed in Cairo, Egypt — this was before major unrest — and I attended a private school with great teachers. An Apple fellow on sabbatical taught me to program in HyperCard in seventh grade.

02:52 – Anthony Presley:
Summers in the States, my friends and I bought computer games with cash and hacked the copy protection to share them — pre-internet days. Back home as a teenager, I needed a job. My high school ended up paying me to write software for a Valentine’s dance — a matching program for students. I built a tiny app that paired classmates; none of those couples lasted, but it sparked my software path. I launched small software companies in high school and college.

03:33 – Anthony Presley:
Around 2000, my college roommate worked at his uncle’s restaurant across town without a car. He needed to see the posted schedule Sunday nights, but the single phone line had to stay open for customers. I’d drive him to check the schedule for gas and pizza money. We joked about how inefficient that was — I didn’t know it would someday lead to building a product.

05:15 – Anthony Presley:
I ran several software companies, some with 60–80 employees, doing custom development. That’s how I entered the industry: deep tech background, almost worked in a restaurant, then took an alternative path.

05:37 – Jason E. Brooks:
Who knew you were matchmaking in high school — that’s awesome. And yes, I remember driving to see schedules posted on the wall.

06:11 – Jason E. Brooks:
Back then, managers posted on time because no one wanted multiple trips. Today some schedules still go up late. Also, your Cairo story is wild — tech is in your bloodstream.

07:07 – Anthony Presley:
Thanks — it’s the story I’ve got.

07:15 – Jason E. Brooks:
Labor is a major pressure point: compliance, scheduling, and keeping great people. How do leaders shift the conversation from managing schedules to actually leading better teams?

07:57 – Anthony Presley:
Great question. Post-COVID, the lens changed. Roughly 40% of our customers are in grocery and general retail, the rest in restaurants, so we see patterns across industries. There’s been turmoil among frontline workers. During COVID, many tenured managers left restaurants.

08:49 – Anthony Presley:
Today the average restaurant manager has under two years’ tenure, and it’s shrinking. In the past, a seasoned manager had gut knowledge — knowing the Thursday/Friday patterns, sidewalk sales, how to lead. Now many are new, so leadership must emphasize communication: clearly conveying business needs to the people who execute. Command-and-control may work briefly, but sustainable leadership is goal-setting, guidance, and development.

10:23 – Anthony Presley:
Restaurants spend heavily to attract guests, but often spend little on retaining employees. If you invest even a fraction into training, education, and reskilling, you build a healthier organization — and those people take care of your customers.

11:04 – Anthony Presley:
Smart leaders clearly set priorities and expectations, then tie them to rewards. Many frontline workers live near poverty levels — it doesn’t have to be that way. Hit goals, share bonuses or spiffs, and suddenly people don’t need three jobs.

11:46 – Jason E. Brooks:
Quick pause: if this resonates, check out my Aim Drive Scale Leadership Circle — details in the show notes. Back to the episode. Your platform reflects what you’re saying — it goes beyond scheduling to recruiting, recognition, retention, and multi-vertical support.

13:41 – Jason E. Brooks:
Growth can erode culture if leaders aren’t intentional. How do you scale your product while keeping trust and culture at the center? First, within TimeForge; second, how you help customers.

14:25 – Anthony Presley:
A short story from our founding. We built the first version in 2007 to bring automated scheduling and communication to restaurants. I showed it to a table-service CEO who said, “I already pay managers to build schedules. Why would I pay you?” That hit hard. I asked, “What is your real problem?” He said compliance and time tracking, plus onboarding and HR issues.

16:05 – Anthony Presley:
So we listened and built what customers needed. Over time we formalized that into continuous feedback loops — it’s the Business Model Canvas approach I now teach to students: talk to users, validate the problem, find decision makers, and build what matters. Sometimes the pain isn’t “turnover,” it’s a management issue. You learn that by asking better questions.

17:19 – Jason E. Brooks:
You started ideating in 2000, built in 2007, and kept iterating. I saw recent updates: gig worker functions, Square POS integration, TripleSeat partnership, AI forecasting. You haven’t slowed down. Zero sleep or a strong team?

18:34 – Anthony Presley:
Maybe both — plus we share the same barber. We’ve had machine learning since version one, but we’ve expanded it. Interest is surging: a 7,000-location manager recently asked for an agentic AI to build schedules and flag labor rule violations. We integrate with 40–50 POS systems. Gig work matters because some stores can’t open without it; healthcare used similar models for decades, restaurants and retail are catching up.

20:40 – Jason E. Brooks:
Our industry is often a late adopter. What separates tools that overwhelm managers from tools that actually help?

21:26 – Anthony Presley:
I think in modules. Pick the one or two capabilities that move the needle, not the entire suite. Managers already touch dozens of apps; sprawl creates clutter. Consolidation cycles happen, then people add point tools again. Helping means choosing the right module, then doing real change management so processes match the tool — otherwise adoption fails.

24:02 – Jason E. Brooks:
Agreed. Too often brands choose tools for head-office needs without asking frontline teams what would actually help. We also over-index on top 5% performers instead of the 95% of stores that work differently. Tech should fit the real environment.

27:22 – Anthony Presley:
Exactly. Also, before switching, evaluate whether your current system already does what you need — features get turned off or forgotten. Think through the lift of change. Don’t pilot for one week at one store and roll out system-wide.

28:41 – Jason E. Brooks:
Tech is a dashboard. Decide what teams must see daily or hourly; the rest is nice-to-have. And context matters: an airport unit needs different indicators than a food truck. One brand, multiple environments, tailored views.

29:41 – Jason E. Brooks:
Let’s close with signature questions. If you could sit at a leadership table with three leaders from any era, who would they be and why?

30:48 – Anthony Presley:
I knew this was coming. My three: Seth Godin for his marketing-meets-leadership lens; Mark Cuban for contrarian, tech-savvy business building; and Ken Blanchard for situational leadership and The One Minute Manager. That mix would spark useful debate.

32:45 – Jason E. Brooks:
That board would get things done. Final question: one conversation that profoundly shaped you as a leader?

33:23 – Anthony Presley:
In February 2015, after raising venture capital, I got a call transferred from reception — a very upset woman. She said her separated husband had passed away by suicide, leaving her and the kids with nothing but his last paycheck and life insurance. I didn’t recognize her at first, but I paused, chose empathy, and asked questions.

35:01 – Anthony Presley:
It turned out I had met her a decade earlier and knew her husband. She asked, “Did you get our Christmas presents?” He had told her for years that he worked for me. He didn’t. He parked in our large lot, took a bus to another job, and created a story to feel like he was providing. We unraveled it over days; there was no paycheck or policy.

35:53 – Anthony Presley:
It was heartbreaking, and it changed me. You never truly know what others are carrying. Lead with questions and empathy — people’s stories are complex and often invisible.

37:15 – Jason E. Brooks:
I’m glad you listened to that voice. Empathy changes outcomes in leadership interactions every day.

38:23 – Jason E. Brooks:
Before we wrap, where can listeners connect and learn more about TimeForge?

38:44 – Anthony Presley:
I’m easy to find — search Anthony Presley and connect on LinkedIn. You can also visit timeforged.com.

39:08 – Jason E. Brooks:
Anthony, thank you for showing how leadership and technology together lift people and profits. If you found value here, subscribe, leave a review, and share with a leader navigating today’s workplace. Visit jasonebrooks.com/podcasts for more tools. Until next time, manage, lead, coach, and repeat. Anthony, thank you so much.