About the Role:

Ovative is at an inflection point - building an AI-native agency model on top of EMRge, our established proprietary marketing intelligence platform, with the ambition to double the business over three years. As CTO, you will own the technology vision that makes that possible and lead the engineering organization that delivers it.

You will lead all of Ovative's engineering capabilities: the teams building EMRge and the AI Operating System (AI OS) that connects our internal tools into a coordinated, agent-driven system. You will serve as a member of Ovative's Executive Leadership Team - the senior-most technology leader in the company, accountable not just for technical direction but for engineering delivery, team health, and the technology reputation of the firm with clients and the market.

EMRge drives measurable business impact through a unified data foundation, actionable measurement, and business intelligence solutions - used by our team to deliver results and empower our clients with the data & insights they need to plan and grow their business. The AI OS is an integration and orchestration layer - connecting Claude, Glean, ClickUp, Slack, Outlook, and others - that enables intelligent, multi-step automated workflows across the business.

This role demands both depth and breadth: executive leadership over an established engineering organization, hands-on architectural judgment to build something net-new, and the credibility to represent Ovative's technology externally to clients, partners, and the industry.

Role Responsibilities:

Technology Vision & Strategy:

• Own - not just translate - the technology vision for Ovative; set strategic direction that achieves near- and long-term business goals and convert it into a technology product roadmap in partnership with Product Management
• Oversee the architectural direction for both EMRge and the AI OS, ensuring systems are built to scale and adapt.
• Lead the evolution and enforcement of engineering standards across the organization: reliability, scalability, security, observability, CI/CD practices, and infrastructure-as-code - so deployments are repeatable, auditable, and low-risk.
• Represent Ovative's technology vision externally: with clients, prospective clients, and industry forums - building credibility that supports business development and client retention.

EMRge Platform Engineering:

• Lead EMRge engineering - the Databricks data lake, platform services, client-facing capabilities, and infrastructure that power our core products - by directly leading the Engineering Senior Director to set direction, remove blockers, and hold the team accountable to a high bar.
• Partner with Product Management to align engineering capacity to highest-impact roadmap priorities; maintain SOC 2-compliant, enterprise-grade engineering practices.

AI Operating System:

• Lead the architecture and delivery of Ovative's AI OS - the integration and orchestration layer connecting Claude, Glean, ClickUp, Slack, Outlook, and other tools into a system that automates meeting intelligence, action item execution, write-back to operational systems, and knowledge management across the business.
• Own the security and governance framework for the AI OS - ensuring it meets enterprise standards from the start, in partnership with IT and Security
• Drive build vs. buy decisions and Ovative's AI vendor and model portfolio; make pragmatic, business-grounded choices that balance speed, cost, and long-term flexibility.
• Establish LLMOps practices across all AI-powered systems: output evaluation, cost attribution, observability, and model lifecycle management

Engineering Leadership

• Attract, develop, and retain a diverse, high-performing team of engineers - currently 35 engineers across 6 product teams and a client delivery function - setting clear accountability, career paths, and a high bar for technical craft at every level.
• Manage AI infrastructure and LLM inference costs proactively, ensuring costs are delivering impact.
• Own engineering hiring strategy and technical bar: define what great looks like at every level and build the talent pipeline that sustains growth.

Executive Leadership:

• Serve as a full member of Ovative's Executive Leadership Team - influencing company vision, strategy, and priorities, communicating and advocating for technology vision across the organization.
• Translate technology strategy for non-technical stakeholders including executive leadership, clients, and business partners - making complex decisions legible and building organizational confidence in the technology direction.
• Act as a technology thought partner to the CEO and business leadership - proactively surfacing risks, opportunities, and technology trends that affect Ovative's competitive position.

Qualifications:

Required Qualifications

• 18+ years of engineering experience; 7+ years leading engineering managers in high-growth environments - with a track record of delivery, not just direction
• Proven track record as a hands-on technical leader - able to engage credibly at the architecture and system design level, not just the organizational level.
• Demonstrated experience architecting enterprise integration and orchestration systems - connecting SaaS platforms, APIs, and data sources into coordinated workflow layers, including bidirectional write-back to operational systems.
• Production experience with LLM-based systems: RAG pipelines, agent orchestration frameworks, MCP or equivalent tool-use patterns, and LLMOps practices including output evaluation and cost management
• Experience operationalizing security requirements in systems with broad organizational reach: access controls, credential management, audit logging, and principles of least privilege.
• Strong build vs. buy instincts - vendor evaluation, contract management, and pragmatic integration vs. custom build judgment.
• Experience with cloud data infrastructure (AWS, Azure, or GCP); Databricks experience strongly preferred.
• Clear communicator across technical and non-technical audiences - engineers, product partners, clients, and executives; comfortable in board-level and client-facing conversations

Preferred Qualifications

• Prior IC background in software, data, or ML/AI engineering
• Experience building platforms where the primary users are non-engineers - adoption and enablement mindset, not just technical delivery.
• Experience with Claude Enterprise or the Anthropic API
• Familiarity with marketing technology, measurement, or analytics-heavy SaaS environments
• External thought leadership: conference speaking, technical writing, or industry presence in AI or data engineering

Pay Transparency:

At Ovative, we offer a transparent view into three core components of your total compensation package: Base Salary, Annual Bonus, and Benefits. The salary range for this position below is inclusive of an annual bonus. Actual offers are made with consideration for relevant experience and anticipated impact. Additional benefits information is provided below.

For this position, the compensation ranges from $385,000 - $476,000, which is inclusive of a 40% bonus.

Benefits of Working at Ovative Group:

We provide strong, competitive, holistic benefits that understand the importance of your life inside and out of work.

Culture:

Culture matters and we've been recognized as a Top Workplace for ten years running because of it. We demand trust and transparency from each other. We believe in doing the hard and complicated work others put off. We're open in communication and floor plan. We're flat - our interns sit next to VPs, our analysts work closely with senior leaders, and our CEO interacts with every single person daily. Put together, these elements help foster an environment where smart people can support each other in performing to their highest potential.

Ovative is committed to fostering an inclusive environment where everyone can participate and thrive. We do not tolerate discrimination of any kind, including on the basis of race, sexual orientation, gender identity, or gender expression. Our policies reflect this commitment-for example, our medical leave benefits are inclusive of same-sex partners, ensuring equitable care and support for all families.

Compensation and Insurance:

We strive to hire and retain the best talent. Paying fair, competitive compensation, with a large bonus incentive, and phenomenal health insurance is an important part of this mix.

We're rewarded fairly and when the company performs well, we all benefit.

Tangible amenities we enjoy:

• Access to all office spaces in MSP, NYC, and CHI

• Frequent, paid travel to our Minneapolis headquarters for company events, team events, and in-person collaboration with teams

• Generous paid vacation policy

• 401k match program

• Top-notch health insurance options, inclusive of same sex partners

• Family formation benefits including reimbursement options for fertility, pregnancy, and parenting needs

• Monthly stipend for your mobile phone and data plan

• Sabbatical program

• Charitable giving via our time and a financial match program

• Shenanigan's Day

Working at Ovative won't be easy, but if you like getting your hands dirty, driving results, and being surrounded by the best talent, it'll be the most rewarding job you'll ever have. If you think you can make us better, we want to hear from you!