On the Horizon: SailPoint’s College-to-Career Pipeline Ensures a Bright Future for Cybersecurity

From its new graduate orientation program to its leadership development courses, this identity security company is bridging the gap between textbooks and tech, sailing toward a more diverse, authentic and empowered workforce.

Written by Jenny Lyons-Cunha
Published on Mar. 23, 2023
On the Horizon: SailPoint’s College-to-Career Pipeline Ensures a Bright Future for Cybersecurity
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When SailPoint's Director of Crew Member Success Christine Gilberto logged onto the early-morning Zoom interview for this article, she immediately lit up. She had spotted Alexiss Medina, a first-year DevOps engineer. 

“Alexiss!” she exclaimed, waving with both hands. “It’s so good to see your face!”

Realizing others were also on the call, Gilberto laughed and added, “Hi, everyone,” explaining, “I haven’t seen Lexi since our Sail-U program last summer.” 

This exchange is the kind of glowing rapport anyone would crave on a work call — and a manifestation of SailPoint’s bespoke career-development pipeline, which includes the Sail-U program for incoming college graduates.

In her role at Sailpoint, Gilberto develops the company’s suite of talent-management programs, which are designed to help crew members grow their skills and careers.  

“We’re evolving these programs into something bigger than we are now,” she said. “Our employees are getting the experience they might get at a much larger organization.” 


An image of the SailPoint Crew Cafe


Partners in Growth

Gilberto partners with stakeholders across the company to build custom pipelines for each facet of SailPoint’s operation. One such partner is Megan Kay, director of enablement. Kay shapes the training for SailPoint’s salespeople and client-facing professionals. In the program Gilberto and Kay have built, salespeople develop through numbered levels, which they parlay into career growth and leadership roles.



SailPoint provides cutting-edge identity security for the cloud enterprise. Its identity security solutions secure and enable thousands of companies worldwide, giving customers visibility into their digital workforce and ensuring workers have the right access to do their job. The service-minded industry attracts a specific caliber of talent, Gilberto said. “We absolutely attract a certain mindset — we tend to attract that type of talent who wants to help others,” she said. 


“We’re asking new professionals to call clients with 20 years of experience — that’s scary,” Kay emphasized. “The goal with this system and our programs is to build their confidence from day one.” 

“Christine Gilberto and I are working closely together to pair the technical hard skills on the sales side with soft skills at Sail-U,” Kay continued. “We’re looking at how we bring those together to help our team members succeed and want to stay here forever, hopefully.” 


SailU participants at an outdoor event.


Sailing Into the Workforce  

The crown jewel of SailPoint’s learning and development program is Sail-U, an internship-to-new-hire pipeline that gives new graduates a foothold at the company. 

“The identity security business requires a high level of technical skills, so we’ve historically hired mid-level people,” Gilberto explained. “We want to give new grads the opportunity to learn and become the SailPoint leaders of the future.” 


“Identity security requires a high level of technical skills, so we’ve historically hired mid-level people. With Sail-U, we give new grads the opportunity to learn and become SailPoint leaders of the future.”


Sail-U is the second step of a robust internship program — “A new-hire orientation on steroids,” Gilberto said — that plugs fresh graduates into SailPoint’s workforce. The three-week program is held in person at the company’s Austin headquarters. There, Sail-U participants get a crash course on each part of the business, hear from senior leadership and get acquainted with life as a tech professional. To smooth the transition from university life to work life, content is presented in both classroom and active-learning formats.   



  • A mentorship-style buddy system 
  • Student-led hackathons
  • Organization-wide presentations
  • Active-learning opportunities
  • Bonding events like a ping pong tournament  
  • Fun learning mediums like “water pong” trivia games 


Perhaps most importantly, the immersive program is anchored in SailPoint’s vision for a more diverse future in tech.  

“We partner very intentionally with universities who have diverse student bodies,” Gilberto said. “We all know the tech field doesn’t breed a lot of diversity, so this is a chance to tap into pools that are being missed by the labor market.” 

“It’s a great opportunity for new grads to start their career journey together as a cohort,” Gilberto added. 

For her part, Kay loves the promise of a long-term partnership that Sail-U brings.

“There’s nothing better than a story of someone who starts with us in college and rises up to become a future leader and mentor for the next generation,” she said. 


SailU participants at a STEM event.


‘They Didn’t Really Go Over That in College.’ 

Medina — who interned with SailPoint before entering the Sail-U program and workforce — had a lot to say on the topic of Sail-U.

 “Before I started here, I had no idea what DevOps even did,” said Medina, who majored in computer science and minored in business data. “They didn’t really go over that in college.” 

For Medina, the three-week intensive helped her find her footing as a professional and SailPoint crew member. She recalls feeling nervous about navigating the workplace out of college but found comfort in starting her journey with a cohort of freshly minted graduates. 

“You quickly realize you’re not the only one struggling with imposter syndrome,” Medina said, nodding. “Sail-U gives you the chance to overcome those problems together.” 


“You quickly realize you’re not the only one struggling with imposter syndrome. Sail-U gives you the chance to overcome those problems together.”


Sail-U impressed upon Medina the power of the individual contributor at SailPoint. She came away from the program with a sense of how her DevOps role fits into the overall company framework — and was inspired to nurture that personal impact. 

The program places quality of work and healthy work-life balance on equal pedestals, training Sail-U attendees to prevent burnout. 



At SailPoint, growth isn’t reserved for new grads. As a part of a larger suite of development programs, “Leading the SailPoint Way” is a course reserved for leadership at the identity security company. “People leaders are in the best position to affect change, drive our culture and ensure development is happening,” Gilberto said. The program equips them with the tools to tackle compensation conversations, self-regulate their own development and be culture carriers at SailPoint. 


Medina has gleaned another tool that transcends healthy work-life hygiene and workplace literacy: confidence. 

“Being a part of the program and team, I can see my growth every month,” she shared. “I feel more confident in my ability to find answers and share my ideas.” 

This conviction reaches beyond hard and soft skills at SailPoint. Like many of her Gen Z peers, Medina was nervous about entering a workforce that might not yet have space for her — she grew up on horror stories about companies where identities go uncelebrated and work is uninspired. 

“I came here kind of scared, but even as an intern, I quickly realized I don’t have to pretend, I don’t have to change my personality,” she said. “I can still interact with everyone in a genuine way.” 

As the end of the interview neared, Medina jumped enthusiastically back into the conversation.

“Wait, I need to gush about my mentor before we log off!” she said. “They’ve been so awesome at reassuring me that they’ve shared all the same struggles and fears — that it’s all normal.” 

“It’s all about creating that safe space,” Gilberto chimed in. “If we’re not creating that safety and bringing the person behind you along the way with you, what are we doing?” 

“It’s why I love our programs so much,” she added, beaming.


Responses have been edited for length and clarity. Images provided by SailPoint.

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