Chief Technology Officer / VP Engineering
12 - 15 years
United States
Full-time
Remote
1 month ago
About the role
Company Description
FOG Software Group is a part of Constellation Software Inc. (TSX: CSU), operating under Vela Software. Backed by over 25 years of experience, Constellation Software is a global leader with a market capitalization exceeding $80 billion. As a division of this powerhouse, FOG Software Group focuses on delivering tailored and innovative software solutions to meet a diverse range of industry needs, fostering long-term growth and success.
About the Role
We are seeking an experienced Chief Technology Officer to lead engineering through a focused transformation mandate: structuring a right-sized, high-performing engineering organization, driving meaningful cost reduction, and rapidly embedding AI capabilities across an established enterprise software product. This is a hands-on operational role for a leader who is energized by execution over vision.
The CTO will be the senior technical voice both internally and with key accounts, balancing near-term cost discipline with a credible product roadmap that gives customers reason to renew and expand.
What You Will Do
Engineering Restructuring & Cost Reduction
AI Adoption & Product Modernization
Product Stewardship & Customer Confidence
What We Are Looking For
Required
Strongly Preferred
What Success Looks Like
The Ideal Candidate
You are an operator, not a visionary. You get more satisfaction from shipping working software on a tight budget than from presenting ten-year platform roadmaps. You have done the hard work of restructuring teams, know how to maintain trust with customers through difficult internal transitions, and have a pragmatic, product-first view of where AI creates real near-term value. You are not here to rebuild the architecture — you are here to make a good product better and run it well.
Compensation & Structure
FOG Software Group is a part of Constellation Software Inc. (TSX: CSU), operating under Vela Software. Backed by over 25 years of experience, Constellation Software is a global leader with a market capitalization exceeding $80 billion. As a division of this powerhouse, FOG Software Group focuses on delivering tailored and innovative software solutions to meet a diverse range of industry needs, fostering long-term growth and success.
About the Role
We are seeking an experienced Chief Technology Officer to lead engineering through a focused transformation mandate: structuring a right-sized, high-performing engineering organization, driving meaningful cost reduction, and rapidly embedding AI capabilities across an established enterprise software product. This is a hands-on operational role for a leader who is energized by execution over vision.
The CTO will be the senior technical voice both internally and with key accounts, balancing near-term cost discipline with a credible product roadmap that gives customers reason to renew and expand.
What You Will Do
Engineering Restructuring & Cost Reduction
- Design and execute a significant reduction in engineering run-rate costs, including headcount rationalization across multiple geographies
- Consolidate redundant infrastructure, tooling, and vendor contracts without compromising product stability
- Build and manage a leaner, distributed engineering organization across a global team
- Establish clear accountability structures, delivery cadences, and performance standards in a post-restructuring environment
AI Adoption & Product Modernization
- Identify and ship high-impact AI features within the existing product — targeting quick wins that drive customer retention and upsell
- Prioritize practical AI integrations over architectural reimagination
- Build vs. buy decision framework for AI capabilities that balances speed-to-market against R&D cost
- Translate AI wins into customer-facing narratives that support renewal conversations and competitive positioning
Product Stewardship & Customer Confidence
- Maintain product stability and supportability across a large, diverse enterprise installed base during the transition period
- Act as technical executive sponsor for strategic accounts, particularly during renewal cycles
- Own the technical roadmap and communicate it credibly to customers, prospects, and the board
What We Are Looking For
Required
- 10+ years in engineering leadership, including at least one role as VP Engineering or CTO
- Demonstrated experience leading engineering through a cost reduction or restructuring cycle — you can speak specifically to headcount and run-rate outcomes
- Track record of shipping AI features into a legacy or mature product (not building AI-native products from scratch)
- Experience managing distributed engineering teams across multiple geographies, including nearshore or offshore
- Comfort operating in a capital-disciplined, hold-forever software environment where cash generation matters more than growth multiples
Strongly Preferred
- Experience at a PE-backed or acquirer-owned software business through a value creation plan
What Success Looks Like
- In the first 90 days: Engineering cost structure is mapped, reduction plan is developed, and quick-win AI opportunities are identified and sequenced.
- At 6 months: Run-rate cost reduction is substantially underway, first AI features are shipped or in beta, and the engineering org is operating with clear accountability.
- At 12 months: Engineering is structurally right-sized, P&L is stabilized or improving, and the product roadmap is credibly differentiated in the market on the basis of AI capability.
The Ideal Candidate
You are an operator, not a visionary. You get more satisfaction from shipping working software on a tight budget than from presenting ten-year platform roadmaps. You have done the hard work of restructuring teams, know how to maintain trust with customers through difficult internal transitions, and have a pragmatic, product-first view of where AI creates real near-term value. You are not here to rebuild the architecture — you are here to make a good product better and run it well.
Compensation & Structure
- Competitive base salary commensurate with experience
- Performance-based incentive linked to cost reduction milestones and revenue targets
Skills
Software DevelopmentInformation Technology