Email Marketing Specialist

We operate a portfolio of vacation rentals and timeshare resort properties. We are seeking an experienced Email Marketing Specialist to build, configure, and optimize high-converting email flows and follow-up sequences for our existing customer base using our custom CRM and SendGrid setup. Key Responsibilities Flow Architecture & Copywriting: Design, write, and structure lifecycle email flows targeting existing guests and past bookers. Automation Setup: Configure triggers, delays, and dynamic logic tailored to user booking history and travel dates. Existing Customer Re-engagement: Craft strategic follow-up campaigns to drive repeat bookings, off-season stays, and loyalty offer redemptions. Deliverability & System Integration: Coordinate with our development team to ensure custom CRM event triggers integrate cleanly with SendGrid to maintain optimal inbox placement. Deliverability Management & Technical Setup: Audit and maintain domain authentication protocols (SPF, DKIM, DMARC, and custom return-path/tracking domains in SendGrid) to maximize primary inbox placement. Inbox Placement & Spam Prevention: Monitor sender reputation, IP/domain health, bounce rates, and spam complaints across major ISPs; implement proactive list hygiene and suppression rules for unengaged contacts. Inbox Landing Optimization: Craft, test, and optimize subject lines, preheaders, and email code (HTML/CSS structures, image-to-text ratios) to bypass promotional tabs and avoid spam triggers. Required Email Flows to Build Pre-Arrival Sequence: Booking confirmations, check-in instructions, property amenities guide, and upsell opportunities (late check-out, room upgrades, local activities). This is mostly setup, but open for review and imporvement. Post-Stay Follow-Up: Departure thank-you, review generation requests, and post-stay feedback collection. Re-Engagement & Win-Back: Targeted outreach for past guests based on stay anniversaries, seasonal travel patterns, or 6/12-month inactivity. Repeat Guest / Loyalty Campaign: Special offers and priority booking windows exclusive to existing customers. Qualifications & Experience Proven Experience: 3+ years managing lifecycle email marketing, ideally within the hospitality, vacation rental, or travel sectors. Copywriting & Design Skills: Strong track record of writing persuasive, brand-aligned email copy and designing mobile-responsive HTML templates. Technical Proficiency: Hands-on experience working with custom CRMs or API-driven email setups (SendGrid, Mailgun, or similar transactional platforms). Deliverability & Data: Deep understanding of email deliverability best practices, list segmentation, and key performance metrics (open rates, click-to-book ratios, revenue per email). How to Apply Please submit your portfolio or examples of past email flows you have built (copy and design), along with a short summary of your experience working with travel brands or custom email platforms.