Email Marketing & Customer Retention Specialist (Lifecycle Marketing & Automation)

Email Marketing & Customer Retention Specialist (Lifecycle Marketing & Automation) Looking for an Expert to Help Build Our Customer Retention System Hi, I'm the owner of Traveling Baby Company, a nationwide marketplace that connects traveling families with independently owned local baby equipment rental providers throughout the United States. We've been in business for over 20 years and process several hundred orders each month. We have a successful business with a solid reputation, but one area we've never really focused on is customer retention marketing. That's where I need your help. Unlike a traditional ecommerce business, our customers typically rent baby equipment only when they travel. A family may rent from us for a Disneyland vacation this year and not travel again until next summer—or they may travel to a completely different destination the next time. Because of that, I'm not looking for someone who applies the same ecommerce playbook to every business. I'm looking for someone who enjoys thinking strategically about a unique customer journey and can help me build a retention marketing system that actually fits my business. Who I'm Looking For I'm not looking for a large agency. I'm looking for one experienced person who has personally built successful email, SMS, and customer lifecycle marketing systems and wants to work directly with a business owner. Communication, strategic thinking, honesty, and real-world experience are much more important to me than flashy presentations or sales pitches. If your primary experience is SEO, PPC, social media management, graphic design, or virtual assistant work, this probably isn't the right project. What I Need Help With I'd like someone to review my customer journey and help me build a complete customer retention system. Some of the areas I'm interested in include: Welcome email sequences Welcome SMS sequences Abandoned quote recovery Abandoned checkout recovery Customer review automation Referral programs Customer reactivation campaigns Travel reminder campaigns Customer segmentation Email templates SMS templates Reporting dashboards A/B testing Recommendations on whether Brevo, Klaviyo, GoHighLevel, or another platform would be the best fit for my business I'm not saying I need every one of these. I'm looking for someone who can help me determine what will actually produce the biggest impact. My Business Philosophy I'm very ROI-focused. My business operates on relatively small margins, so every marketing dollar has to earn its keep. I'm not looking to build dozens of automations simply because they can be built. I'm looking for someone who isn't afraid to tell me what not to do. If there are only five automations that will make a meaningful impact on my business, I'd much rather build those five correctly than build twenty mediocre ones. I'm looking for thoughtful recommendations—not the biggest possible project. How I'd Like to Start I'd like to begin by having you review my business, understand my customer journey, identify the biggest opportunities, and recommend the best path forward. If we're a good fit, I'd like to continue into implementation and, ideally, build a long-term working relationship. Please Answer These Questions 1. Tell me about one lifecycle marketing project that you personally built that produced exceptional results. What exactly did you do? 2. If you were hired tomorrow, what are the first five automations you would recommend building for Traveling Baby Company? Please explain why. 3. Based on what you've read, would you recommend staying with Brevo, or would you recommend Klaviyo, GoHighLevel, or another platform? Please explain your reasoning. 4. What metrics would you monitor during the first 90 days? 5. Approximately how many hours would you expect for: Initial setup Ongoing monthly management after the system has been established 6. Have you worked with businesses that have long customer purchase cycles instead of customers who buy every month? If so, please describe the business. 7. Please provide examples of lifecycle automations or email flows that you personally designed and implemented. 8. Tell me about one lifecycle marketing project that didn't go well. What happened? What did you learn? Before You Apply Please begin your proposal with the words: Traveling Families This lets me know you've actually read the posting. I receive a lot of proposals on Upwork. I'm much less interested in reading a list of every platform you've used than I am in understanding how you think. If you believe Traveling Baby's business model presents unique retention marketing challenges—or opportunities—I would genuinely like to hear your thoughts. Thoughtful proposals will stand out far more than generic lists of credentials. Final Note The strongest candidates will be invited to a Zoom interview. I'm looking for someone I can build a long-term working relationship with, so communication, honesty, and strategic thinking are just as important to me as technical skills.