Services
$270 / month
Start free, decide later
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1
Free 7-day trial
No charge until day 7. Cancel anytime. -
2
Ongoing calls + chat
2 × 50-min calls per month, unlimited Q&A. Replies in 24 hours or less. -
3
No lock-in
Month to month, no contract.
MentorCruise summary
Simon is an Executive Coach for Software Engineers and a former Upstart engineer. He started his engineering career at Upstart in 2013 and helped the company grow from four engineers to 400. He has contributed to, led, and managed Product, Data, and Platform Engineering teams. He helps software engineers communicate more clearly, frame their experience for interviews, and earn promotions or move into senior roles.
Based on 4 verified mentee reviews
- Reviewers often praise his coaching on communication, including framing mistakes as growth in interviews and communicating more clearly day to day.
- Two reviewers mention targeted practice and advice for framing experience and answering interview questions.
About
I started my engineering career in 2013 at Upstart, building it from 4 engineers to 400. I’ve contributed, led, and managed Product, Data, and Platform Engineering teams. I’ve created and executed an org-wide internship program and coached numerous engineers 1:1, from fresh boot camp grads to industry veterans.
I help engineers communicate effectively, regardless of their level. We can work together to:
- Protect your job, or get you to the next level
- Flourish under a stubborn, opaque, or selfish manager
- Build prestige within your company
- Rally other teams around your designs
It's easy to find a coworker or instructor to help you write the code, but often our challenges stem from people, not technology. A good manager can help, but most managers are spinning hundreds of plates and can't spend that much time on one engineer. I've been there, and I can help you push through it.
Together we will alter how your peers and leads perceive you, amplifying your impact and advancing your career. Schedule a call, today.
What mentees say
5 out of 5 stars
Wonderful experience working with Simon on my soft skills and communication style. It was difficult for me to express mistakes and challenges live during interviews. Simon showed me an effective strategy to do so, framing these experiences in such a way as to demonstrate growth and development. We practiced them together until they were delivered effectively. Highly recommended for anyone looking to succeed in their career progression!
Jeff
Standard Plan • 2 months
5 out of 5 stars
Simon helped me land my first title as a Senior Data Engineer. For years I'd struggled with defining myself on the job market and framing my experience in a way that felt both authentic to me, but also concise enough for an interview format. With targeted advice and encouragement, Simon was able to train me in a few meetings how to answer questions like 'tell me about yourself?' and, 'why do you want to leave?' which I had struggled with. He was definitely a difference maker for me going into final round interviews. I'd be glad to work with him again. Thanks Simon!
Christopher
Standard Plan • 2 months
5 out of 5 stars
Arnab
Standard Plan • 3 months
Get to know Simon
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Article 5 min readSimon’s Blog | Simon Lepkin | Substack
Writing about the stuff I like to talk about. Mostly the non-technical parts of software engineering. Sometimes other things, probably. …
Read more
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Article 5 min read"I'm just not good at this"
How to catch the harmful lies of your inner monologue and find a better path forward
Read more
What happens when you start
You tell Simon your goals. They see exactly what you want to work on before session one.
You meet within days. Simon reviews your application and books your first session, usually within a day or two.
You leave with a plan. Concrete next steps and a weekly rhythm from your very first week.
