About Ovative Group:

Ovative Group is an independent, full-funnel media, measurement, and creative firm transforming how brands grow. We partner with leading names like American Eagle, Best Buy, Domino’s, The Home Depot, Polaris, and UnitedHealth Group to build smarter media and measurement programs that drive real, profitable growth. 

We don’t just track performance—we redefine it. Powered by our proprietary intelligence platform, EMRge, and our holistic metric Enterprise Marketing Return (EMR), we help brands connect revenue, customer, and brand outcomes into one clear picture of success. Our approach to full-funnel strategy, buying, and measurement delivers results that matter—and it’s getting noticed. Our work has been recognized by Digiday, Google, USA Today, Inc. 5000, and Search Engine Land.

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 on an annualized basis, with the potential for an annual bonus of up to 40% of base salary.

Working at Ovative Group:

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

At Ovative, culture isn’t a buzzword—it’s the reason we’ve been named a Top Workplace for ten years running. We lead with trust, transparency, and a commitment to doing the hard work others avoid.

We offer flexibility. You'll work from our Minneapolis, Chicago, or New York office on set days each week, and an option to work remote on others.

Our open floor plan reflects our open communication and flat structure—where interns collaborate with VPs, analysts partner with senior leaders, and our CEO engages with every team member. Together, we create an environment where smart, driven people can do their best work and support one another in the process. 

We’re equally committed to inclusion and belonging. Ovative fosters a workplace where everyone can participate and thrive—regardless of ethnicity, gender, sexual orientation, gender identity, or expression or other protected class status. Our benefits and policies reflect that commitment, from inclusive medical leave coverage for same-sex spouses to equitable care and support for all families. 

Benefits: 

We strive to hire and retain the best talent by offering fair, competitive compensation, a meaningful bonus program, and excellent health coverage. When the company performs well, we all benefit. 

Some tangible benefits and 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  

Additional information can be found at Ovative's Career Page.

The details of the benefits are covered by applicable plan documents for group benefits and by company policies where a plan document does not apply.

Working at Ovative won’t be easy—but if you like challenging, hard work, driving results, and being surrounded by the best talent, it has the potential to be the most rewarding job you’ll ever have. If you think you can make us better, we want to hear from you! 

EEO & Accessibility: 

Ovative is an Equal Opportunity Employer committed to a respectful, inclusive workplace for all. Applicants receive consideration without regard to legally protected characteristics (e.g., color, religion, creed, national origin, sex, pregnancy, childbirth and related conditions, sexual orientation, gender identity/, gender expression, gender identity, age, physical or mental disability, marital/ status, familial status, military or veteran’s status, genetic information, status with regard to public assistance, and any other status protected under applicable law). 

We provide reasonable accommodations consistent with the Americans with Disabilities Act and applicable state law to qualified applicants and employees with disability, unless doing so would create an undue hardship.

If you need assistance or accommodation at any stage of the application or interview process due to a disability, please contact us at [email protected].

Application Details and Process: 

Applicants must be legally authorized to work in the United States for any employer on a full-time basis, without current or future need for visa sponsorship. Ovative is unable to sponsor or take over sponsorship of an employment visa for this position. In compliance with federal law, all persons hired will be required to verify identity and eligibility to work in the United States and to complete the required employment eligibility verification documentation upon hire.

Open Until Filled or Otherwise Withdrawn:

We encourage interested candidates to apply early. The position will remain open for at least 10 business days from the first day of posting. After this time, if the position has not been filled, the posting will remain open until the position is filled, or until the posting is otherwise closed or withdrawn for business reasons.