Hello, I'm Ben Stiefel.
I'm an engineering leader who merges technical expertise and strategic thinking to deliver the best results - both in products and people. I've learned the ins and outs of building and growing great software engineering teams across dozens of industries and companies.
Details
- Professional CategoryInformation Technology
- Location
- Years of Relevant Experience20+ years
- Seniority LevelExecutive
- Consulting Rate (Hourly)275
Headline
Scaled engineering teams multiple times. Know when to push vs pause, how to navigate the chaos of growth. 25 years in the code, 10 years leading teams. Shipping great products with great people. Open to fractional CTO/VPE/advisory roles.
Experience
Senior Director / Head of Engineering
SydecarJanuary 2024 - October 2025Forged the technical vision and roadmap for a VC-backed Fintech startup, spearheading product
development, platform engineering, and R&D initiatives.
Championed and delivered our inaugural SOC2 Type 2 certification, transforming security posture
from minimal awareness to audit-ready in 12 months.
Scaled the Engineering organization from 10 to 25 staff with 95% retention, established core delivery processes and strategic alignment with Product and Design, reducing project timelines by over 50% while maintaining bug rate below 5%.
Spearheaded the launch of two new products and major platform improvements, driving
revenue growth that doubled company performance.
Led execution of strategic OKRs, maturing engineering and cross-functional capabilities to
support rapid scaling and enhanced customer experience.
Director of Engineering
MeasurablAugust 2018 - January 2024• Led initiatives to increase ARR of our core application, went from $9M to $15.5M and was the only product line in the company to surpass growth goals.
• Reduced Cycle Time for engineering from over 50 hours to below 10, across all teams. Monthly deployments went from 1 per 2 weeks up to over 1 per day.
• Managed the company’s core SaaS application, scaling the division from 2 to 6 product focused teams, managing 3 Engineering Managers. Hired 28 employees over 6 months. Built effective engineering teams using a value centric approach focused on trust and high performance.
• During my tenure as Director, I have had zero attrition and maintained the highest approval rating of any manager in the company, and significantly above national average. Using Culture Amp, over 3 years my minimum favorable score was 84%, US average is 74%.
• Collaborated with senior Engineering leadership to establish mature practices such as Operations Duty, feature ownership, outsourcing vendor policies, engineering driven feature processes and more. Coached team leadership to drive consistency and predictability in delivery and release reliable, observable software.
• Defined and implemented strategic initiatives across Engineering and other departments to position company to grow sales opportunities globally and into new market segments. Worked with counterparts in Product and other Engineering divisions to align teams with the company's strategic goals.Led initiatives to increase ARR of our core application, went from $9M to $15.5M and was the only product line in the company to surpass growth goals.
• Reduced Cycle Time for engineering from over 50 hours to below 10, across all teams. Monthly deployments went from 1 per 2 weeks up to over 1 per day.
• Managed the company’s core SaaS application, scaling the division from 2 to 6 product focused teams, managing 3 Engineering Managers. Hired 28 employees over 6 months. Built effective engineering teams using a value centric approach focused on trust and high performance.
• During my tenure as Director, I have had zero attrition and maintained the highest approval rating of any manager in the company, and significantly above national average. Using Culture Amp, over 3 years my minimum favorable score was 84%, US average is 74%.
• Collaborated with senior Engineering leadership to establish mature practices such as Operations Duty, feature ownership, outsourcing vendor policies, engineering driven feature processes and more. Coached team leadership to drive consistency and predictability in delivery and release reliable, observable software.
• Defined and implemented strategic initiatives across Engineering and other departments to position company to grow sales opportunities globally and into new market segments. Worked with counterparts in Product and other Engineering divisions to align teams with the company's strategic goals.
Industry
- Financial Services
- Technology, Information and Media
Specific Jurisdictions That I'm Qualified In or Can Cover
United States: California
Language(s)
- English
Professional Interests
Environment, Social, Governance, Mentorship, Education Technology, Continuous Learning, Climate Technology
I am interested in
- Professional / Business Networking
- Career Opportunities
- Providing Services based on my Expertise