Engineering Career Real Talk: AMA with Leopard Engineering Leaders
Hi all! I like to do virtual AMAs once in awhile when I feel like there's a good discussion to be had! And right now I think a lot of folks could use a good career advice AMA.
Engineering as a career feels pretty up in the air right now, and the job seems to be changing every 3-6 months. We're hearing a lot of career uncertainty from members and wanted to create a space to talk candidly about questions like:
My company is pushing AI into everything, but I'm not sure it's making me a better engineer 😬
I'm spending more time managing agents than writing code, how do I make sure I keep my skills sharp? ⚙️
Do I even want to be doing this five years from now? 💔
I'm really excited to bring together two incredible engineering leaders, Jenny Donnelly and Leslie Carr to share their wisdom with us and answer our many questions and give advice.
Note: this is an AMA, so we'll spend ~ 50-60% of our allotted time on community questions. So bring whatever is on your mind re: engineering careers, AI, IC vs. management paths, vetting companies, skill development, etc
Meet our amazing Engineering Leaders:
Jenny Donnelly 💙 | Former CTO, The Pill Club | Senior Director of Engineering, Pinterest | Founder, Granite Tech Advisory
Jenny has 20+ years of experience growing from a hands-on software engineer to CTO and leading engineering organizations of 60+ people. Most recently, she led full-stack product and ML teams at Pinterest, working on recommendation systems, LLM integrations, and AI-driven engineering workflows.
Previously, Jenny was CTO of The Pill Club, Head of Platform Engineering at Nextdoor, and spent 14 years at Yahoo, progressing from Senior Engineer to Senior Director. She's worked across startups and large tech companies, with deep experience in engineering leadership, distributed systems, ML, and technical strategy.
Today, Jenny runs Granite Tech Advisory, helping engineers and engineering leaders grow into their next roles, and will be joining a startup as a VP of Engineering very soon!
Leslie Carr 💜 | Director of Engineering, Fastly | Former Senior Director of Engineering, Slack/Quip | Founder, Summerstir Solutions
Leslie has over 20 years of engineering experience, starting in network and infrastructure engineering at Google, Craigslist, Twitter, and Wikimedia before moving into engineering leadership.
Today, she leads Fastly's Compute Platform organization, overseeing distributed systems, edge computing, developer tools, and developer experience. Previously, she held engineering leadership roles at Quip, Slack, Trusted Health, and Pando, where she helped grow engineering teams at different company stages.
Leslie is also an engineering leadership coach through Summerstir Solutions. She's especially passionate about helping engineers navigate career growth, develop leadership skills, and build strong, supportive teams.
About Leopard.FYI: Leopard is a free community and job-search platform for senior+ women and genderqueer software engineers (& allies!). We have 4,000+ members, including 700+ actively exploring new roles. All members are Senior-level or above, 25% are Staff/Lead/Manager+, and half join through referrals!
We partner with hundreds of startups to help engineers find great jobs. We're typically working on 200+ engineering roles across SF, NYC, and remote, spanning Backend, Full Stack, Frontend, AI/ML, Infrastructure, DevOps, and more.
Membership is completely free and includes:
Warm introductions to hiring companies with transparent salary bands and detailed insights into culture, teams, tech stacks, interview processes, and working norms.
Daily live interview prep sessions for coding, system design, behavioral, and hiring-manager interviews.
Active Slack communities for technical interview prep, job-search support, resumes, negotiation, AI, and more.
Virtual mentorship and coaching with experienced engineers, career coaches, and engineering leaders.
In-person meetups and events in SF, NYC, LA, Seattle, Boston, DC, Denver, and more.
Next Steps:
Want to start or reactivate your job search? Book with Alejandra https://calendly.com/alejandra-leopard/checkinwithleopard?from=slack
Refer a Friend to Leopard and get referral bonuses!
Is your company hiring? Email lexi@leopard.fyi or grab time with Leopard's CEO