William Wolfe

Tell me about yourself and your journey into big tech.

I’m the third combat generation in my family, with service in nearly every conflict since World War II. I enlisted in the US Army Reserves when I was 17 and have continued to serve for over 23 years. After my initial training, I returned home to start my first semester at SFSU. However, 3 months into it, I had to drop out since I was deployed to Iraq for 15 months from 2003-2004. Needless to say, I grew up fast and was exposed to a lot in a short span of time.  

Upon returning from my first deployment, I focused on pursuing law enforcement and continuing my education. This was in part due to my confidence established from my overseas experience. I told myself, “If I could handle patrols on the streets of Baghdad and Fallujah, I could handle myself anywhere!” So I ultimately put myself through the police academy, while attending night classes at SFSU, and from then on, I spent close to the last 18 years in law enforcement. 

I loved my job and my colleagues. I loved deep-diving investigations, assembling operations plans, executing search warrants with my SWAT team, and cultivating forensic evidence from cell phone downloads. However, there were a myriad of factors that drove my desire to hang up the badge and achieve something more. 

First and foremost was my family. The detective callouts in the middle of the night, the SWAT operations, and the multiple hats worn for so many roles began to require more of my time at work than at home. I was missing out on seeing my kids grow up and I decided that nothing would stop me from getting into tech in the private sector. On top of that, I essentially capped out or eclipsed in my line of work. There was not much else I could do and I wanted to make more of a global impact. 

I have heard this echoed among many in law enforcement. We pigeonhole ourselves into thinking that all we can do is just that, law enforcement. This is not the case and I refused to allow the badge to become my identity. 

I got started by learning how my complex problem solving skills and ability to operate in fast-paced environments were transferable to the tech industry. I also learned from friends and former officers who had found their niche in the private sector which was truly inspirational. This opportunity through Pinkerton at Roblox is personal to me since my kids use this gaming platform. In a way, I’m continuing my protection of them but in a different capacity.

In your current role, what does a typical day look like and what are your main job responsibilities?

My official role is to serve as an embedded Protective Intelligence Analyst, under the umbrella of Global Security at Roblox. I essentially conduct threat assessments and investigations for various bad actors and offenders on the Roblox platform, but there’s so much more to it. I liaise and network with law enforcement counterparts, as well as revise and update emergency operations plans or SOPs, regarding the risks and vulnerabilities of our operational environment. I also work closely with the GSOC (Global Security Operations Center) in the open sharing of intelligence and further exploring of nefarious activity across the whole spectrum. Lastly, I deep dive OSINT (open source intelligence), as well as the dark web and deep web data. 

In just my short span of time since starting, I absolutely love what I’m doing in my day-to-day operations. It truly feels like I’m back in the Investigations Bureau as a Detective but with much less risk and liability than that of a law enforcement officer. I’ve really enjoyed the pace because no day is the same. It’s always different and there is always something for me to explore and deep dive into.

What advice do you have for others who want to break into big tech or do what you do?

I decided I wanted to transition into the tech industry this past May and by June, I sent my cut and paste resume to over 50 companies. I was under the impression that I would be picked up immediately and I could not have been more wrong!

I am so thankful and grateful to the many mentors that helped me along the way after realizing the job market would be more challenging than I had originally anticipated. Some were close friends and some were family, but the majority were complete strangers that I connected with on LinkedIn. Through my journey, I learned the importance of establishing credibility on LinkedIn, the true meaning of networking, how to write a tailored resume, and the power of building high-quality relationships and friendships.

That might sound a little cliché or cheesy, but that’s truly the nature of this business. I found the best results by being authentic and genuine, being myself, being open minded with a desire to learn, being vulnerable, and never asking for anything in return. As a result, my final interviews with Meta, Amazon, Uber, and ServiceNow were all due to internal referrals that I never asked for. Although I did not get the offers I wanted, I still expressed my thanks to those who interviewed me and have maintained those relationships. 

My most valuable advice is to remain forged with resilience! Never give up, never quit, and embrace being told no. Use that to fuel your drive and internal fire, to find another door, or to make your own. It took me 6 months to land a role and I am forever grateful for all of my rejections because it strengthened my mental resiliency.

What’s your favorite thing about working at Roblox?

My favorite thing about working for Pinkerton at Roblox? I don’t even know where to begin because there is not just one thing alone by itself. You see, all I ever knew was government work or public service. If you were to put any former law enforcement officer or military veteran in my place, especially after serving for so long, Roblox would be an immediate breath of fresh air. I would even venture to say that many other tech companies would have a similar effect on someone coming from government. So, I say this with the caveat that I never knew what it was like to work in an environment like this, since I have nothing to compare it to.

But I will say that my manager, and up to the Senior Director, are all great people to work for. They offer sound advice and value my opinions and advice as well. No one acts like they’re above anyone else.

The job itself makes it fun, but throw in a relaxed culture, great environment, endless snacks, drinks, a coffee bar and food, secured onsite parking, the capability to work a flexible schedule, a brand new facility, and a 4-mile commute? I have no room to complain.

Finish this sentence. Outside of the office, you can find me:

Staying busy with my family and spending quality time with our kids, all in between our Army Reserve obligations since we are dual service parents. 

Aside from that, my true alone time is spent paying it forward by helping others in their transitional journeys, revising resumes, and preparing people for interviews - all for free like others have done for me!

Brenna’s key takeaway from this week’s coffee chat

As we head into the new year, William’s story is a powerful reminder that it’s never too late to pivot or make a career change.

By understanding what his transferrable skills were and by learning from others who had already made successful career changes, he was able to build a winning strategy for his job search.

If you’re considering a career change, here are a few ideas to get you started:

Assess and identify your transferrable skills

Start by identifying the transferable skills you possess. These skills are valuable across various industries and roles.

Network and build connections

As we saw in William’s story, networking can be a game changer for your job search. Start by connecting with individuals in your desired industry through LinkedIn, networking events, or professional groups. These connections can provide valuable insights and lead to potential referrals or job leads.

Customize your resume

Speak to the job you want, not the job you have. Rewrite your resume to emphasize your transferrable skills and highlight your experiences that align with the new role and industry you are applying to.

Learn new skills and fill gaps

Recognize any gaps between your current skillset and the needs of the new roles you are going for. Consider enrolling in courses, obtaining certifications, or gaining relevant experience through freelance or volunteer work to boost your qualifications.

Research potential careers

Read job descriptions for roles you're interested in to understand the required skills and experiences needed. Pay attention to the minimum qualifications listed.

Find mentors

Similar to William, find a mentor in your desired industry who can offer guidance, advice, and support. A mentor can provide valuable insights from their own experiences and help you navigate the transition more smoothly.

Thank you so much for taking the time to read today’s newsletter!

Please note, since the next two Tuesdays fall on Christmas Eve and New Year’s Eve, the next Coffee Chats newsletter will hit inboxes on January 7th.

Early next year, we have some amazing guests lined up including a Product Manager from Microsoft, Account Executive from Salesforce, Brand Strategist from Meta, and more!

With that, I hope you have a wonderful holiday season and end to the year! See you in January!!! ❄️🌲 Cheers, Brenna

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Other ways I can help you

Download my personal resume template: It has helped me land interviews at companies like Meta, Google, TikTok, Salesforce, and Uber.

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