$300 / month
2 calls per month (60min/call)
Unlimited Q&A via chat
Expect responses in 2 days
Steve is a Director of Engineering at Toast. He has more than 25 years of software engineering experience as an individual contributor, manager, and director. His background includes building software, leading teams, and shaping engineering strategy. He helps engineers move into management, develop leadership skills, and turn career concerns into actionable steps.
Based on 3 verified mentee reviews
I have 25+ years of experience as an individual contributor, manager, and director in software engineering. I'm passionate about providing guidance to others through active listening, asking pertinent questions, and helping people draw their own conclusions. I am open to mentoring people at all levels of their tech careers, from entry level IC to fellow Directors of Engineering. I offer a short introductory call for free to ensure there's a mutual fit.
From me, you can expect guidance and advice in the form of pragmatism, perspective taking, and finding ways to convert your thought processes and concerns into actionable steps.
5 out of 5 stars
A well-rounded technology executive with diverse experience and a balanced perspective. Our conversations felt like thoughtful exchanges with a seasoned leader over coffee.
Standard Plan • 1 month
5 out of 5 stars
Standard Plan • 1 month
5 out of 5 stars
It was nice to find Steve, another local Chicagoan. Steve has mentored me for about 3 months and shown the journey of an engineering manager from a compassionate lens. As a senior engineer interested in management, Steve was able to share what it takes to get there and the skills and values required once you're there. Management isn't for everyone, but Steve can help you find out if it's the right path for you.
Standard Plan • 3 months
Mentees who work with a mentor for 3+ months reach their goals 2x faster than those going it alone. Long-term mentorship means fewer false starts, more focused sessions, and support that builds week after week.
97% satisfaction across all mentors
Personalized feedback and growth plans
Trusted by thousands of mentees
Steve Sobel
Director of Engineering at Toast
Enter your email and we'll let you know when Steve has open spots. You'll also get a link to manage your wishlist – no account needed.
Book a free intro call with Steve
Connect with Steve in a quick call (usually under 30 minutes)
What's included in the trial?
Every trial is a little different–here's what Steve says about their trial:
We'll meet for a quick call (usually under 30 minutes) where we:
- Break the ice and introduce ourselves
- Discuss your goals and how I can support you
- Coordinate logistics like time zones, meeting frequency, and communication methods
