WorkRamp raises $40M Series C!


Lifelong Learning with Joe Montana – His Career Journey From Super Bowl MVP to World-Class Investor

Lifelong Learning with Joe Montana – His Career Journey From Super Bowl MVP to World-Class Investor

NFL Hall of Famer Joe Montana knows how to thrive under pressure. The former 49ers quarterback who earned three MVP titles and four Super Bowl rings during his 16 season career has spent recent years making a name for himself in another Bay Area arena—the VC world of Silicon Valley. 

Joe—whose world-class investment portfolio includes Pinterest, GitLab, Rippling, and WorkRamp—recently joined us for an exclusive customer event to share behind-the-scenes takes from his iconic NFL career, along with lessons on handling stress, embracing failure, and celebrating individual strengths in an organization.

How to stay [Joe] cool under pressure

With just under one minute left in the 1981 NFC championship game against the Dallas Cowboys, things were not looking good for the San Francisco 49ers, who were down 27-21. In a miraculous play—known simply as “the catch” to football fans—Joe Montana threw a six-yard touchdown pass that led the 49ers to victory, kicking off the team’s NFL dynasty of the 1980s.

Iconic plays like “the catch” earned Montana the nickname “Joe Cool” among fans awestruck by the quarterback’s ability to remain calm in high pressure situations. But to Joe, these moments were simply a matter of getting the job done. “If you put in the work and are prepared, good things will happen,” says Joe. “It’s about how you come into work every day, not about how you prepare for the big meeting.”

For enablement managers tasked with creating and administering up-to-date learnings and certifications, every day brings a to-do list of time-sensitive projects. These daily stressors are compounded by competing needs from different departments and the constant updates that come with new releases and product launches. Joe reminds us that we can mitigate stress for ourselves by focusing on time management and better preparation. Lessen your burden ahead of time by building solid foundational practices—it’ll make onboarding, content creation, and reporting that much easier down the road. 

Embracing the “I” in team

While the old adage “there’s no I in teamis often heralded in workplaces and sports settings, Joe holds a different philosophy. In learning the fundamentals of teamwork as a rising star at Notre Dame, Joe discovered that football is “a team game, but it’s also about the individual.” 

In reality, Joe argues, there should be an “I” in team, where individuals are encouraged to sharpen their strengths for the good of the larger organization. Individual group members should take time to reflect on the capabilities that only they can bring to the team. Ask yourself, “what can I do to make myself better that will in turn make my team better,” encourages Joe.

This outlook is especially relevant in enablement, as onboarding and training programs directly impact employee success, and therefore, overall company performance. Enablement professionals are in a perfect position to leverage their unique talents in coaching and knowledge-sharing to make major contributions to their organization, making a case for embracing the “I” in enablement. It’s unique, individual perspectives—like that of an enablement manager with past experience as an account executive or in sales operations—that make for better, more effective trainings.  

Become better by failing forward

Under the leadership of longtime 49ers head coach Bill Walsh, Joe gained valuable insight into the benefits of failure. “We’re all going to make mistakes, so the biggest thing is how you recover from that mistake,” says Joe. “What do you do? Do you put so much pressure on yourself that you compound it and make it worse?” The better option, Joe learned, is to use a moment of failure as an opportunity to reflect, “take a step back and consider ‘what did I do? What caused that?’”

Embracing failure has proven beneficial throughout Joe’s career. “Business is a team, too. It’s about how you treat people when they make a mistake,” urges Joe. Combined with a fail-first attitude, Joe still aims for perfection. “If you strive to be perfect and you miss, you are still pretty good,” offers Joe with a smile. 

The idea that failure presents an opportunity to grow has become a mainstream doctrine for many organizations in recent years—but that certainly doesn’t make mistakes easier to process. By promptly entering a reflective state, as Joe suggests, we become solution-oriented, better preparing ourselves for the next time we encounter a challenging situation.  


This exclusive interview with Joe Montana is part of the WorkRamp VIP experience for our customers and partners. To learn about future VIP events and other WorkRamp VIP membership perks, email us at 

Ready to Get Started?

Get in touch to learn how WorkRamp can help you achieve your training goals.

Request a Demo