Head of Engineering

TRANZACT is a leading direct-to-consumer insurance services business, specializing in the distribution of Medicare Advantage, Medicare Supplement and Life & Supplemental insurance policies. Our focus is on leveraging our highly skilled team of over 3,000 professionals to deliver innovative solutions for our insurance carrier partners and provide consumers with a best-in-class experience.


We work with some of America's largest insurance brands to attract, educate and connect with consumers. Our diverse team of analysts, writers, engineers, designers, business leads, data scientists and sales professionals all work together to create thoughtful, data-driven and effective marketing, technology, sales and servicing strategies. These efforts have resulted in TRANZACT earning recognition and winning awards from some of the biggest names in the industry.

When you become part of TRANZACT, you join a team of passionate people who push for excellence, follow through on commitments, and love to succeed together. Our culture rests on a simple principle - "Be Real" - that means being genuine, keeping your word, and having the courage to make tough decisions. Our "Be Real" values resonate and are meaningful to us. We are entrepreneurial, fast paced and empower our people. We know how to make things happen and know that our people are always the source of our success.

We are hiring a hands-on engineering leader to own the technology behind TRANZACT's direct-to-consumer marketing and pre-sales experience-the websites, martech platforms, and conversion systems that attract, educate, and convert millions of consumers. You will own the architecture, delivery, performance, and accessibility of our consumer-facing web properties built on Umbraco, while serving as the technical leader for marketing initiatives that extend well beyond the websites themselves-from ad platforms and tag management to experimentation and conversion rate optimization. This role combines strategic platform ownership with sleeves-rolled-up execution and leadership of a multi-team organization. You will lead by example, staying close enough to the details to set the technical bar while developing the managers and engineers who deliver against it.

What you'll Own:

• Define and evolve the end-to-end strategy for TRANZACT's direct-to-consumer marketing web platform-content management, site performance, accessibility, and reliability-anchored on Umbraco, with a production-grade consumer experience across devices.
• Serve as the accountable technical leader for marketing and pre-sales initiatives that reach beyond the websites, including paid media instrumentation, tag management, analytics, and the systems that connect marketing to the sales funnel.
• Establish an AI-first engineering practice: standard patterns, golden paths, and tooling that use AI to accelerate development, testing, documentation, and operations across marketing engineering teams.
• Own conversion rate optimization as an engineering discipline-experimentation infrastructure, A/B testing, and the data instrumentation needed to measure and improve funnel performance.
• Build and lead high-performing engineering teams through their managers-hiring, mentoring, and setting the technical bar-while driving measurable improvements in delivery velocity, site performance, and conversion outcomes.
• Serve as the accountable leader for critical marketing technology initiatives, driving requirements → architecture → implementation → launch → post-launch learning.

The responsibilities of the Head of Engineering include:

• Architect scalable, reliable, and accessible consumer web experiences on Umbraco, with strong site performance, SEO health, and compliance with accessibility standards (e.g., WCAG).
• Own the marketing technology stack that instruments and optimizes acquisition, including Google Ads, Google Tag Manager, analytics, and Optimizely, ensuring accurate measurement and clean data flow across systems.
• Lead conversion rate optimization: design and run A/B and multivariate experiments, and translate results into engineering and content changes that move funnel metrics.
• Define and roll out an AI-first engineering workflow-leveraging AI coding assistants, agentic tooling, and automated eval/QA gates-to accelerate outcomes without compromising quality, performance, or security.
• Set engineering standards and review designs, PRs, and architecture across the marketing engineering teams; drive adoption through documentation and enablement.
• Partner closely with Marketing, Product, Design, Analytics, and Sales stakeholders to translate business goals into technical roadmaps and measurable results.
• Lead vendor and tooling evaluation, and make build/buy/insource recommendations aligned to unit economics, reliability, and IP strategy.
• Recruit, mentor, and develop managers and engineers; cultivate a culture of ownership, experimentation, and continuous improvement, leading by example in the details.

Success Profile (6-12 Months):

• The marketing web platform reliably supports key consumer journeys with strong performance, accessibility, and uptime, backed by clear SLOs and runbooks.
• Marketing instrumentation (ad platforms, tag management, analytics) is accurate, well-governed, and trusted as the basis for optimization decisions.
• A structured CRO practice is operating, with a healthy experiment cadence and documented conversion improvements.
• An AI-first engineering practice is established, with reusable templates and golden paths measurably increasing delivery velocity across teams.
• Teams are staffed, aligned, and performing through their managers, with healthy delivery and quality signals.
• At least one critical marketing technology initiative is led to launch with documented business impact and a retrospective feeding the roadmap.

Minimum Qualifications:

• 8+ years in software engineering with a focus on direct-to-consumer digital marketing and web platforms; 3+ years leading engineering teams, including leading through other managers.
• Deep, hands-on experience managing consumer-facing websites with a modern CMS-Umbraco strongly preferred-including content management, site performance, and accessibility.
• Proven expertise across the digital marketing technology stack: Google Ads, Google Tag Manager, analytics, and Optimizely (or comparable experimentation platforms).
• Demonstrated ownership of conversion rate optimization, A/B testing, and the instrumentation required to measure and improve funnel performance.
• Proven, hands-on experience leveraging AI to accelerate engineering outcomes (e.g., AI coding assistants, agentic tooling, LLM-assisted development, testing, or operations).
• Strong engineering fundamentals and the ability to stay hands-on-reviewing designs and code and leading by example while managing a multi-team organization.
• Excellent communicator and mentor, effective with stakeholders across technical and non-technical domains, including Marketing, Product, and Sales.
• Bachelor's degree in Computer Science or related field required.

Preferred Qualifications:

• Master's degree in Computer Science, Marketing Technology, or a related field.
• Experience in insurance, healthcare, financial services, or other regulated, consumer-facing industries.
• Experience with .NET / C# (the Umbraco ecosystem) and modern front-end frameworks in production.
• Familiarity with SEO engineering, Core Web Vitals, and performance monitoring/observability for consumer web.
• Experience integrating marketing and pre-sales systems with downstream sales, CRM, or lead-management platforms.
• Cloud-native experience on Azure and/or AWS, with strong infrastructure-as-code and CI/CD practices.

How we work:

• AI-first: we use AI to accelerate engineering while protecting proprietary data and process IP.
• Agile and iterative: prove value quickly, then scale with governance and reliability.
• Responsible by default: performance, accessibility, security, and continuous evaluation built in from the start.

Compensation and Benefits

Base salary range and benefits information for this position are being included in accordance with requirements of various state/local pay transparency legislation. Please note that base salaries may vary for different individuals in the same role based on several factors, including but not limited to location of the role, individual competencies, education/professional certifications, qualifications/experience, performance in the role and potential for revenue generation.

Compensation

The base salary compensation being offered for this role is $180,000 USD per year.

This role is also eligible to participate in the annual bonus program.

Company Benefits

TRANZACT provides a competitive benefit package which includes the following (eligibility requirements apply):

• Health and Welfare Benefits: Medical (including prescription coverage), Dental, Vision, Health Savings Account, Health Care and Dependent Care Flexible Spending Accounts, Group Accident, Group Critical Illness, Life Insurance, AD&D, Group Legal, Identify Theft Protection, Wellbeing Program and Work/Life Resources (including Employee Assistance Program)
• Leave Benefits: Paid Holidays, Annual Paid Time Off (includes state/local paid leave where required), Short-Term Disability, Long-Term Disability, Other Leaves (e.g., Bereavement, FMLA, ADA, Jury Duty, Military Leave, and Parental and Adoption Leave)
• Retirement Benefits: Savings Plan with annual nonelective company contribution.

TRANZACT is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.


Equal Opportunity Employer/Disability/Vet