Senior Manager, Digital Sales (Remote, Texas)

Insurance Zebra; Town of Texas (WI); Remote; USD 95,000 - 105,000; Full time

Job summary

Join a leading company as a Senior Agency Manager, Digital & Chat, focused on revolutionizing digital engagement. In this role, you'll lead initiatives to enhance customer interactions through innovative digital channels while fostering cross-functional collaboration. Competitive compensation and comprehensive benefits await you.

Benefits

Competitive Compensation & Stock Option Offering

Health, Dental, Vision & Disability Coverages

End early Fridays

Sabbatical program for tenured employees

401k with match

Unlimited PTO

Qualifications

• 5+ years of experience in digital customer experience, product operations, or chat platform management.
• 3+ years of experience leading sales teams.
• Proven track record implementing and optimizing AI-powered chat solutions.

Responsibilities

• Develop and execute a multi-channel digital engagement roadmap.
• Champion seamless digital user experiences to drive self-service.
• Lead the implementation of AI-driven chatbots and live chat systems.

Skills

Digital Customer Experience

Project Management

Cross-Functional Collaboration

Analytical Skills

Communication Skills

Job description

Introduction:

The Zebra, named a Best Place to Work in Austin four years running, is revolutionizing how connected consumers research and shop for insurance. We intentionally strive to build diverse teams that feel inclusive for all. Our motto is "All Stripes Welcome," and we put that into practice by valuing both traditional and non-conventional backgrounds and perspectives. Our Zeebs are passionate about learning, growing, & working together to tackle exciting problems.

We are seeking a visionary and execution-focused Senior Agency Manager, Digital & Chat to lead the evolution of our digital engagement channels across web, mobile, chat, and social. In this role, you will shape and execute the roadmap for AI-enabled customer interactions, champion cross-functional collaboration, and optimize digital customer journeys to enhance satisfaction and drive conversions.

The ideal candidate blends strategic thinking with technical acumen and thrives in fast-paced, cross-functional environments.

Location:

ThisisaremotepositionbasedinTexas.CandidatesmustresideinthestateofTexasandbeauthorizedtoworkintheUnitedStates.OurHQisbasedinAustin,Texas.Whetheryoupreferthestructureofanoffice,theconvenienceofremotework,oramixofboth,wesupportwhatworksbestforyou!

What You'll Do:

• Develop and execute a multi-channel digital engagement roadmap across web, mobile, chat, and social platforms.

• Champion seamless digital user experiences to drive self-service, reduce friction, and support growth.

• Lead the implementation and continuous optimization of AI-driven chatbots and live chat systems.

• Drive internal adoption, training, and performance of digital chat tools in partnership with data and engineering.

• Oversee vendor relationships and evaluate new technologies that support digital engagement goals.

• Act as a cross-functional connector between product, engineering, CX, marketing, and sales ops.

• Define and track KPIs like CSAT, NPS, containment rate, and conversion metrics to inform improvements.

• Use insights to test, iterate, and regularly audit digital touchpoints for quality and consistency.
  

What We're Looking For:

As we evaluate candidates across all roles, we look for folks with a strong sense of ownership, great communication and collaboration skills, and a dedication to continuous improvement.

• 5+yearsofexperienceindigitalcustomerexperience,productoperations,orchatplatformmanagement,ideallyinafast-pacedtechoragencysetting.

• 3+yearsofexperienceleadingsalesteams.

• Proven track record implementing and optimizing AI-powered chat and live chat solutions at scale.

• Strong project management and vendor oversight skills, with an ability to lead cross-functional initiatives from concept to execution.

• Analytical mindset with experience tracking KPIs and using insights to drive strategy and improvements.

• Excellent communicator with the ability to translate between technical and non-technical stakeholders.

Interview Process:

• Recruiter Interview (30 mins): Screens for overall fit, digital leadership experience, and interest in the role; covers resume highlights, team collaboration, and compensation expectations.

• Hiring Manager Interview (30 mins): Evaluates strategic digital expertise, cross-functional leadership, and ability to drive measurable outcomes through digital channels.

• Final Panel (2.5 hours): Assesses functional knowledge, collaboration across departments, team leadership, and culture fit through scenario-based questions and multiple interviewers.

Benefits & Perks:

Inclusive and healthy environments are crafted intentionally. All of our employees can join and participate in (or create your own!) Employee Resource Groups. Here are some other wonderful perks of working here:

• Competitive Compensation & Stock Option Offering

• Health, Dental, Vision & Disability Coverages

• End early Fridays (wrap up work at 2pm CST on Fridays!)

• Sabbatical program for tenured employees

• HSA offering + employer contribution

• Fertility support through Carrot

• $100 monthly wellness perk

• $300 pet reimbursement program

• 401k with match

• Unlimited PTO (paid time off)+ flexibility to enjoy it

• Paid Parental Leave Program

• Learning & Development Opportunities

• Join a team that truly lives their values (outside of the office. Cliche, we know… but we really mean it)

The salary range for this position is $95,000-$105,000 per year. The final salary amount will be determined based on a variety of factors, including experience, skills, internal equity, and insights gained throughout the interview process.

About The Zebra:

The Zebra is the nation’s leading, independent insurance comparison site. With our dynamic, real-time quote comparison tool, consumers can identify insurance companies with the coverage, service level, and pricing to suit their unique needs. Headquartered in Austin, Texas, The Zebra has sought to bring transparency and simplicity to insurance shopping since 2012 -- it's “insurance in black and white.”

We've garnered attention and investment of some of the nation’s top venture capitalists. Check out all of our awards & recognition!

Our core mantra is "All Stripes Welcome." As part of our dedication to maintaining an inclusive and diverse workforce, we provide equal employment opportunities (EEO) to all employees and applicants without regard to race, color, religion, sex, national origin, age, disability or genetics. We will ensure that individuals with disabilities are provided reasonable accommodation to participate in the job application or interview process, to perform core job functions, and to receive other benefits and privileges of employment. Please contact us to request accommodation!