VP of Engineering

Job Description

Language: Fluent English required; conversational Russian required

Travel: International travel required as needed

Salary

$86,000 - $103,000 USD per year

About the company

Caddie is hiring on behalf of an AI-powered sales engagement platform company building tools that help teams identify, enrich, and engage prospects across channels in one system.

Their platform brings together outreach automation, prospect data, AI-assisted workflows, communications tools, and integrations so customers can run high-performance outbound and sales engagement at scale.

They are hiring a VP of Engineering to lead engineering execution and also oversee the product function. This person will be responsible for engineering delivery, technical standards, AI-enabled development workflows, product management alignment, and roadmap execution.

About the role

This is a senior leadership role for someone who combines strong engineering management, hands-on technical depth, product judgment, and operational discipline.

The right person will help scale a platform that sits at the intersection of AI, full-stack software, data, automation, integrations, and user-facing workflow tools. They should be highly effective personally in AI-assisted coding and also know how to implement those practices across a team in a practical, measurable way.

This role is not only about managing engineers. It also includes oversight of the product team, with responsibility for helping align roadmap priorities, customer needs, business goals, and engineering execution.

Responsibilities

• Lead the engineering organization and oversee the product team
• Own engineering execution across product development, releases, reliability, and delivery performance
• Oversee product management, roadmap prioritization, and alignment between product direction and engineering capacity
• Partner closely with founders and leadership to translate company goals into clear product and engineering plans
• Build a strong operating cadence around planning, accountability, ownership, and execution
• Improve development speed, quality, and predictability across the organization
• Establish and scale AI-first development workflows for coding, testing, debugging, documentation, code review, and internal productivity
• Train and coach teams on effective use of AI tools in real software development environments
• Help shape the technical roadmap for a platform involving multichannel workflows, integrations, automation, analytics, and customer-facing product experiences
• Raise the bar on architecture, maintainability, security, performance, and reliability
• Be hands-on when needed in technical reviews, architectural decisions, and critical delivery work
• Help hire, mentor, and strengthen talent across both engineering and product

What they’re looking for

• Proven experience leading engineering teams in a startup or high-growth software company
• Strong track record of improving engineering execution, delivery discipline, and team performance
• Experience overseeing or closely managing product management / product teams
• Significant hands-on experience in full-stack development
• Strong production experience with Python
• Strong experience with React and Electron
• Strong technical fluency across backend systems, APIs, frontend applications, databases, automation, and modern software development practices
• Ability to work across different frameworks, architectures, and implementation approaches depending on product and business needs
• Experience building and scaling SaaS, workflow software, or platform products
• Experience with systems involving integrations, messaging or workflow automation, analytics, user productivity tools, or data-heavy applications
• Demonstrated ability to use AI to improve coding speed, quality, and engineering productivity
• Demonstrated ability to roll out AI-enabled workflows across a team or organization, not just as an individual contributor
• Strong communication, leadership, and decision-making skills

Strong plus if you have

• Experience in sales tech, martech, CRM-connected platforms, workflow automation, or engagement software
• Experience with browser extensions, messaging systems, or communications tooling
• Experience with third-party integrations such as email providers, CRM platforms, automation tools, and external data sources
• Experience leading distributed teams across regions
• Strong product instincts and the ability to balance customer needs, speed, and technical quality

What success looks like

In the first 6–12 months, this person will:

• improve engineering execution and delivery predictability
• strengthen product prioritization and roadmap discipline
• increase team productivity through better systems and better use of AI
• raise the technical bar across architecture, code quality, and development standards
• create clearer ownership and stronger leadership across both product and engineering
• help build a world-class AI-native product and engineering organization

Why this role matters

• This company is building in a category where product speed, workflow quality, AI capability, and reliability matter every day. The VP of Engineering will play a central role in how quickly they ship, how effectively teams operate, and how well product and engineering work together to build the future of sales engagement software.