About the Role

55places.com is the leading online destination for active adults searching for 55+ communities across the United States. We connect millions of prospective buyers — primarily Baby Boomers and Gen X — with the communities, agents, and information they need to make one of the most significant decisions of their lives.

We are looking for an Email Marketing Specialist who is equal parts builder and analyst: someone who can get inside HubSpot or Drip and build a behavioral trigger sequence in the morning, then spend the afternoon in a performance dashboard figuring out why one segment is converting at 2× the rate of another.

This is a hands-on, execution-focused role. You will own the day-to-day operations of our email program while also contributing meaningfully to strategy — segmentation logic, lifecycle architecture, deliverability health, and personalization frameworks that serve an audience with a longer consideration timeline and higher expectations for relevance than most.

This position begins as a contractor engagement, with a clear pathway to full-time employment for high performers. Strong contractors who demonstrate impact will be considered for conversion on a rolling basis.

What You'll Own

Personalization & Segmentation

• Build and maintain behavioral segmentation models using first-party data, including search activity, geographic preferences, community saves, price range, time on site, and content engagement.
• Create dynamic content rules within email templates that adapt messaging, images, and CTAs based on subscriber attributes and behavior — no two active adult buyers are identical.
• Develop audience segments specific to distinct buyer profiles: the actively searching retiree, the pre-retirement planner 3–5 years out, and the adult child researching communities for a parent.t
• Partner with product and data teams to expand the behavioral signals available for targeting, and document segment definitions so the broader team can use them
• Monitor segment performance over time and refine definitions as buyer behavior evolves — especially as Gen X begins to enter the active adult audience in larger numbers.

Marketing Automation (HubSpot & Drip)

• Build, maintain, and optimize automated email workflows across the full buyer lifecycle: welcome series, search-based community alerts, nurture sequences, re-engagement flows, and agent handoff program.s
• Configure trigger logic based on behavioral events — property saves, community page views, search frequency, guide downloads, form submissions — and test timing, branching logic, and send cadence.ce
• Own the integration between the 55places platform and email sending infrastructure, ensuring behavioral data flows cleanly into automation triggers. ers
• Document every workflow with clear logic maps so programs are auditable, maintainable, and improvable without requiring a full rebuild.
• Audit existing automations quarterly for logic decay, stale content, and missed optimization opportunities — then fix them.

List Hygiene & Deliverability

• Own sender reputation health across all 55places sending domains, monitoring daily via Google Postmaster Tools and Amazon SES dashboard.s
• Maintain hard bounce rates below 0.5% and spam complaint rates below 0.1% through proactive list hygiene: suppression management, bounce processing, inactive subscriber handling, and spam trap avoidance.ce
• Run quarterly list-cleaning cycles — identify unengaged subscribers, execute re-engagement sequences, and suppress those who do not respond before they damage the sender's reputation.ion
• Ensure all commercial email programs comply with CAN-SPAM requirements, include a functional one-click unsubscribe, and honor opt-outs within required timeframes.
• Conduct inbox placement testing using tools such as GlockApps or similar before major campaign launches, and maintain a working knowledge of SPF, DKIM, and DMARC configuration.
• Flag anomalies — sudden complaint spikes, unusual bounce patterns, domain blocklist appearances — and escalate or resolve quickly

Analytics & Performance Reporting

• Build and maintain weekly and monthly email performance dashboards covering open rate, click-through rate, conversion to lead, lead quality scores, unsubscribe rate, bounce rate, and revenue attribution
• Run structured A/B tests on subject lines, preview text, send timing, content personalization, and CTAs — document methodology, track statistical significance, and systematically apply learnings
• Analyze performance by segment, lifecycle stage, geography, and buyer type to surface actionable insights rather than just reporting numbers
• Develop email-specific benchmarks for the 55+ audience (industry benchmarks skew toward younger demographics and do not reflect this audience's behavior accurately)
• Present findings clearly to the marketing team and contribute performance context to broader channel discussions

• Hard bounce rate < 0.5% · Complaint rate < 0.1% · Inbox placement rate
• Open rate by segment · Click-through rate · Unsubscribe rate < 0.2%
• A/B test velocity and documented learnings
• Email-attributed leads and lead quality scores
• Nurture engagement rate and agent connection rate
• List growth rate and list health over time

You must have:

• 3–5 years of hands-on email marketing experience, with demonstrable ownership of segmentation, automation builds, and deliverability monitoring
• Proficiency in HubSpot and/or Drip — you have personally built multi-branch automation workflows, not just edited existing ones
• Working knowledge of email deliverability: you understand what SPF, DKIM, and DMARC do, you have used Google Postmaster Tools, and you know what to do when bounce rates spike
• Comfort with data and analytics — you can pull performance reports independently, interpret what the numbers mean, and translate findings into recommendations
• Experience with behavioral segmentation and trigger-based email: you have used real user activity data to personalize and automate, not just demographic list filters
• Strong attention to detail — broken links, incorrect merge fields, and logic errors in automation flows are things you catch before they go out, not after
• Clear, concise written communication — you understand that the 55+ audience values clarity, warmth, and directness over marketing-speak

Nice to have:

• Experience marketing to Baby Boomers, Gen X, or the 55+ demographic — you understand their digital habits and what resonates with a high-consideration, trust-driven audience
• Familiarity with Amazon SES as sending infrastructure, including its bounce and complaint rate thresholds
• Experience with inbox placement testing tools such as GlockApps, Validity Everest, or similar
• Real estate, senior living, or other high-consideration purchase marketing background
• Basic HTML/CSS knowledge for email template troubleshooting — you do not need to be a developer, but being able to inspect and fix a broken template without waiting for engineering help is a meaningful advantage.

Day 30: Complete a full audit of the current email program: automation logic, segmentation definitions, deliverability metrics, list health, and performance benchmarks. Present a written findings summary with a prioritized list of quick wins and longer-term improvements.

Day 60: Launch or rebuild at least one behavioral automation sequence with documented trigger logic and segmentation. Have a deliverability monitoring routine in place, with dashboards active and alert thresholds configured.

Day 90: Own a documented segmentation framework tied to buyer journey stages. Have run at least two structured A/B tests with documented results. Deliverability metrics are at or trending toward target thresholds. You are independently producing regular performance reports.

The 55+ homebuyer is not a passive, hard-to-reach demographic. Baby Boomers are now the largest group of homebuyers in the country (42% of all purchases, NAR 2025), and Gen X — the next wave of active adult buyers — leads all generations in household income. These are digitally active, high-equity, high-intent buyers who use Google, read email carefully, and expect communications that are relevant to where they actually are in their search.

What they do not respond to: urgency tactics, irrelevant content, or communications that treat them as a monolith. The specialist in this role will appreciate that nuance and build programs accordingly.

• Own real programs with real impact — this is not a support role. You will build things, see them perform, and be recognized for the results.
• Work with rich first-party behavioral data from millions of active adult property searches — the kind of segmentation signal most email marketers never get access to
• Clear path forward — this contractor role carries a genuine pathway to full-time employment. Strong performers are evaluated for conversion on a rolling basis.
• Grow quickly — the email channel at 55places is investing and expanding, and strong performers have a clear path toward senior and manager-level roles.
• Mission that matters — you are helping people find the right home for the next chapter of their lives, which turns out to be genuinely motivating work.