Senior Manager, Digital Sales Enablement & Automation (Remote, United States)

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 results-driven and strategic Senior Manager, Digital Sales Enablement & Automation to lead the launch and growth of our digital sales channels—including web chat, mobile messaging, AI bots, and social platforms. In this role, you will own the roadmap for conversational and automated sales experiences, driving conversion, revenue, and customer acquisition. You’ll collaborate cross-functionally to implement scalable, high-impact sales solutions that shorten time-to-sale, enhance customer interactions, and increase close rates.

The ideal candidate has experience with launching chat within a sales platform and blends strategic thinking with technical acumen and thrives in fast-paced, cross-functional environments.

Our employees can choose to work remotely in the U.S. Join us in our Austin, Texas office, or opt for a hybrid setup. Whether you prefer the structure of an office, the convenience of remote work, or a mix of both, we support what works best for you!

Please note - At this time we are not able to hire in California, New Jersey, Massachusetts, and New York.

• 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.
  

We’re looking for someone who’s excited about building great digital experiences and helping teams thrive. If this sounds like you, we’d love to meet you:

• You bring 5+ years of experience in digital sales enablement, customer experience, product operations, or chat platform management, ideally in a fast-moving tech or agency environment.

• You’ve spent 3+ years leading sales teams, and know how to support and grow people while hitting goals together.

• You have a track record of launching and optimizing AI-powered chat and live chat tools that scale and make a real difference for customers.

• You’re a natural project wrangler—comfortable managing vendors, juggling moving parts, and guiding cross-functional projects from idea to launch.

• You think in data: KPIs, dashboards, insights—they’re all in your toolkit to inform decisions and drive improvements.

• You’re a clear, thoughtful communicator who can bridge the gap between technical and non-technical teams with ease.

• 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 (45 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.

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 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!