Rookies to Rockstars

Kevin Heald learned early that doing your job well is only part of the equation. A missed promotion taught him to look beyond his own project. Building a company taught him how quickly a lost contract can put a team’s future at risk.

In this episode of "Rookies to Rockstars," Heald, who most recently served as senior managing director and defense and intelligence portfolio lead at Accenture Federal Services, joins WashingtonExec’s Amanda Ziadeh to share the lessons behind his career in GovCon. 

From a law firm’s basement help desk to leading major defense and intelligence work, he reflects on the risks that helped him grow, the responsibility of making payroll and why leaders need to give teams room to figure things out. Plus, he shares why saying “I don’t know” can build trust, and why no task should be beneath you.

Ross O’Rourke didn’t set out to run a company. Like many in national security, he followed the openings in front of him and said yes to things he wasn’t sure he could pull off. The technical work came first. The leadership came later, once he could see where both the mission and the market were going.

On this episode of “Rookies to Rockstars,” hosts Amanda Ziadeh and Camille Tuutti talk with O’Rourke about building Crimson Phoenix, what it actually takes to scale a mission-driven company and how he leads in today’s national security environment.

He shares lessons from pivotal career moments, the importance of surrounding yourself with the right people, and how he approaches risk, innovation and culture. O’Rourke also reflects on the mentors and experiences that shaped his leadership style, and why staying grounded in purpose continues to guide his decisions.

From early-career uncertainty to leading a growing organization, O’Rourke’s story is a reminder that success isn’t always linear, but it is intentional.

Dr. Yolanda Reid didn't choose national security. She had a competing offer from a pharmaceutical company and picked the National Security Agency because the scheduling lined up better with school. She was 18. She didn't know the difference between the two industries. She just knew someone would pay for college.
In this episode of "Rookies to Rockstars," hosts Amanda Ziadeh and Camille Tuutti  sit down with Reid, vice president of cybersecurity at the MIL Corp., on what it looks like to build a career when you have no roadmap, a lot of candor and occasionally too much of it.

In this conversation, you'll hear about:

• How Reid landed at NSA and what she wishes she'd known about mentorship from day one,
  
  
• The technical director who became her first mentor and why she promptly told him no,
  
  
• What it's like to be the only woman and only person of color in the room for years before you even clock it,
  
  
• How a cancer diagnosis forced her to write her priorities on an index card, and what made the list, and
  
  
• Why she started homeschooling her daughter through first grade from a wheelchair and what that year gave them both.

Reid also talks about leaving government, how she thinks about cyber and AI today, and what she'd tell her younger self about the ideas she let go of too easily when the first answer was no.

At her 5-year cancer-free mark, she and her best friend went to Egypt for two weeks. Fifty people, two groups, ancient history she'd studied alongside her daughter. She loved every bit of it —  except the part where there were 50 people.

Security may be high stakes, but building a career in it isn’t always a straight line.

In this episode of "Rookies to Rockstars," hosts Camille Tuutti and Amanda Ziadeh sit down with Mario Orsini, vice president of security at Nightwing, to talk about the unconventional path that led him from a criminal justice degree to a surprise CIA recruitment call and into the world of national security.

Orsini shares what he wishes he knew early on, including why the security field is “a lot smaller than you think,” and how relationships, reputation and respect can follow you for decades. He also dives into how his communications background became an unexpected advantage, and pulls back the curtain on one of the biggest misconceptions about working in and around the CIA.

In this conversation, you'll learn about:

• Why security professionals are ultimately in a customer service business,
• How to “play in the gray” while still protecting mission and compliance,
• The importance of understanding the “why” behind policies, not just the rules themselves,
• Why saying “yes” early in your career can open doors you didn’t even know existed, and
• How leadership evolves, and why even senior leaders still deal with imposter syndrome.

Orsini also reflects on the real stakes behind security work, where even small missteps can have ripple effects and shares why he prefers picking up the phone over sending “75 emails back and forth.”

And tune in to hear why, according to the motorcycle enthusiast, strong fundamentals — much like navigating with a paper map on the open road — still matter in a world full of advanced technology.

The first lie you believe early in your career is that everyone else knows what they’re doing.

Ben Buckley didn’t. Trained as a biochemist, he walked away from medicine, pushed into technology without the “right” background and took risks that made sense only if you cared more about learning than comfort.

What he figured out early is what most people learn late: uncertainty comes with the work, not incompetence.

In the latest episode of "Rookies to Rockstars," Amanda Ziadeh talks with the GDIT vice president and general manager about building a career by chasing opportunity instead of titles and why progress usually feels messy while it’s happening.

Ben has spent over 16 years at the company, rising from engineer to leading some of GDIT's largest and most complex programs across defense and the intelligence community. He kept choosing roles that stretched him, even when staying put would have been easier.

The conversation keeps coming back to judgment: knowing when to ask questions, when to take a risk and when to slow down long enough to learn from a mistake.

This episode also covers: 

• Nobody has it figured out. Buckley assumed early that everyone else was ahead of him. They weren’t.
• Your degree doesn’t decide your ceiling. Analytical thinking transferred across fields even when job titles changed.
• Risk is the cost of progress. Growth requires it, especially when you push ideas others aren’t ready for.
• Mistakes create experience. Success teaches less. The value comes from stopping long enough to understand what went wrong.
• Proactivity compounds. Asking questions, doing the work and taking initiative separates early leaders from everyone else.

Ben also pushes back on the idea that today’s early-career professionals need to unlearn something. In his experience, many are already ahead: technically sharp, confident and capable of building real things that matter.

Tune in for an honest conversation about risk, learning on the job and how leadership in GovCon is built over time.

Few CIOs can say their careers grew in two worlds at once. For John Pisano, building an IT career while serving in the Army Reserve shaped a leadership style rooted in structure, resilience and a drive to solve hard problems with purpose.

That dual path started early. John’s curiosity for technology pushed him to take apart computers long before he studied IT, and his service taught him discipline and adaptability that carried into every role that followed. Over nearly three decades in uniform and 25 years in industry, he built a career by stepping into unfamiliar work, asking bold questions and learning how the business side of technology really works.

On this week’s Rookies to Rockstars, Amanda Ziadeh sits down with John, CIO of ASRC Federal, to talk about navigating uncertainty, building trust, handling imposter syndrome and redefining success around legacy and collective impact rather than titles.

Today, John leads IT for a major federal contractor, but getting there meant taking risks, embracing lateral moves and leaning on mentors who pushed him to see beyond the next job.

John also talked about:

• How the Army Reserve shaped how he leads and makes decisions
• The business lessons he had to learn by stepping into unfamiliar roles
• Why adaptability became his most important professional skill
• The challenge that taught him simplicity often wins in technology
• The purpose-driven mindset that guided every major career transition

Listen to a grounded, purpose-driven conversation on curiosity, service and what it takes to grow from a hands-on technologist into a leader who shapes teams and missions in federal IT.

Garry Schwartz didn’t begin his career in a boardroom, or even at an intern's desk, for that matter. He joined the military just in time to spend his 18th birthday at boot camp as a kid seeking structure and a purpose beyond himself. Turned out, it was exactly what Garry needed. After serving 21 years in the U.S. Marine Corps, Garry left with a passion for mission, children and a wife to support and a deep understanding of the defense world. That's when he transitioned to industry.

His path wasn’t linear, but it was intentional: follow the mission, make yourself invaluable and keep learning. "Don't worry about failure. Don't worry about not knowing enough and don't worry about looking weak," Garry said.

On this week’s “Rookies to Rockstars,” Amanda Ziadeh sits down with Garry Schwartz, chief operating officer of HII Mission Technologies, to talk about long-game leadership, turning obstacles into opportunities, learning from mistakes and building a career at the intersection of service, mission and innovation.

Today, Garry works with the executive team to drive performance of Mission Technologies’ business portfolio for customers. But getting there meant being bold, proving himself to leadership and trusting a lateral move to eventually lead to bigger and better opportunities. 

We also talked about:

• The mindset shift that helped him transition to industry
• The emotional reality of leaving the military
• Why he now makes himself available to help other transitioning veterans 
• The power of lateral moves
• The hiring mistake he still thinks about
• His advice to those who think their moment has passed: redefine success — because “it’s never too late” if you stay flexible, and
• How industry can better support both early-career professionals and transitioning service members.

Tune in for an honest, mission-driven conversation about service, ownership and the mindset that turns rookies into leaders in GovCon.

David Guffey's trajectory wasn't necessarily thought out. In fact, he mostly searched "for that next opportunity." Once an Airman, guardsman and reservist, what began as a way to serve and see the world in the U.S. Air Force turned into a lifelong journey of learning, leadership and innovation.

On this week’s "Rookies to Rockstars," Amanda Ziadeh is joined by David Guffey, director of U.S. Special Operations Command and Intelligence Community Accounts at Intel Corp., to talk about how adaptability, military and commercial experience, and relationships shaped his path from Airman to industry leader supporting national security missions.

Today, David helps drive cutting-edge technology solutions for some of the nation’s most critical defense and intelligence partners — bridging the gap between commercial innovation and battlefield needs. Yet his path to this work started years earlier, when he left the Air Force and found himself sitting across from program managers and engineers, realizing he had to learn how to speak both languages. That lesson stuck. It taught him that success in defense tech isn’t just about hardware or code; it’s about connecting missions, people and possibilities.

We also talked about:

• The experiences that shaped his perspective on leadership and communication
• His three career principles: don’t expect entitlement, take risks and always be on time
• The culture shift from transitioning from military to industry 
• Building trust across military, government and industry teams
• Why you should "never believe that success is guaranteed"
• The importance of building career relationships over time and maintaining them 
• A risk he took early on that did not pay off, 
• And the challenge of breaking old habits (like relying on military acronyms) and finding a shared language at Intel

Tune in for a conversation about growth, service, overcoming failures, and the evolving intersection of defense and technology.

Heidi Kobylski didn’t start out in tech or business. She started out helping women rebuild their lives in transitional housing in Baltimore. The work was meaningful, but it also revealed something else: She wanted to create impact in a different way.

On this week’s "Rookies to Rockstars," Amanda Ziadeh and Camille Tuutti sit down with Heidi Kobylski, U.S. federal civilian leader at Microsoft, to talk about risk, reinvention and how she built her career one leap at a time.

Today, Heidi leads AI and cloud transformation across federal agencies. But getting there meant detours, missed deadlines and a few defining moments like earning her MBA at night while raising twins, one with special needs.

We also talked about:

• The $18K job that taught her empathy and grit
• The government bid she missed by three minutes—and how it changed her perspective
• Learning to play the long game instead of chasing perfection
• Using data (and courage) to negotiate pay and close the gap
• Why “remote only” can limit early-career growth
• And the surprising way she finds balance: racing cars

Tune in for a  grounded, candid conversation about risk, resilience and redefining success in federal tech.

Amy Foy didn’t wait for someone to hand her a career plan.

Fresh out of college, she joined a leadership program that promised structure and direction. But when it ended, she realized no one was going to chart the next step. If she wanted a career, she’d have to build it herself.

Today, Amy is vice president for contracts and supply chain at Nightwing, leading complex transformation efforts across defense and intelligence missions. Along the way, she’s learned that success isn’t about titles or speed but about owning your path, asking for help when you need it and knowing when to step back.

In this episode of "Rookies to Rockstars," Amy chats about:

• Why your career is your responsibility — and no one else’s
• The mindset that helps you survive high-stakes work and still have a life
• What the next generation needs to unlearn about communication and mentorship
• How she’s redefining ambition after 20 years in the business

It’s a conversation about drive, perspective and the lessons you only learn when you stop trying to do it all yourself.