Itai H.

SendGrid & Email Deliverability Specialist — Multi-Brand Sender Infrastructure Email deliverability and sender-infrastructure expert focused on SendGrid, Mailgun, Postmark, DMARC, SPF, DKIM, return-path, DNS, dedicated IPs and multi-brand sender setups. If your emails are getting blocked by Gmail, Microsoft / Outlook, iCloud, GMX, Web.de or other mailbox providers - or your inbox placement is dropping - I diagnose the exact cause, separate symptoms from root causes, and document the exact fix. WHAT I FIX • SendGrid, Mailgun and Postmark account audits • Sender authentication: SPF, DKIM, DMARC, CNAMEs, return-path and branded sending domains • Microsoft / Outlook / Hotmail 5.7.515 authentication-level rejections • DMARC alignment failures where SPF and DKIM exist but DMARC still fails • Gmail “likely unsolicited mail” blocking and reputation issues • iCloud, GMX, Web.de, Mailcom, T-Online and DACH provider-specific blocking • Return-path / bounce-domain DNS problems, including “Domain not found” rejections • Dedicated IP setup, IP pool structure and sender separation • Multi-brand / multi-domain sender architecture • Subusers, API keys, categories, suppressions, event webhooks and tracking gaps • Transactional vs marketing send separation • List hygiene, suppression management and QA/test traffic leaking into production • Provider-aware dedicated IP warmup and sending ramp-up plans WHO I WORK WITH I work with SaaS, iGaming, fintech, eCommerce, agencies and multi-brand operators sending high-volume email through SendGrid, Mailgun, Postmark or hybrid setups connected to upstream CRMs and marketing platforms such as Smartico, Iterable, Customerio, Braze, HubSpot, Klaviyo, in-house systems and third-party platforms. I am especially useful when the issue is not obvious: SPF and DKIM look “green” but Microsoft still rejects the mail. Gmail says the message is “likely unsolicited.” A return-path subdomain suddenly fails. Clicks or unsubscribes are missing from SendGrid reports. Subusers show no volume while the parent account is sending. A dedicated IP warmup plan is needed, but the current sending path is unclear. WHAT YOU GET • A specific root-cause diagnosis with evidence, not a generic best-practices PDF • A provider-by-provider remediation plan for Gmail, Microsoft, iCloud, GMX/Webde and other major mailbox providers • Clear “do this / don’t do that” priorities • A safe sequence of fixes so you do not damage reputation by changing IPs, DNS or tracking too early • A documented audit your CTO, CRM team, ESP admin or DNS team can execute against • A practical IP warmup or ramp-up plan when dedicated IPs are part of the solution WHY I DO THIS I built and exited Optinize, a marketing-automation SaaS that delivered 3+ billion personalized messages globally and was ranked Top 20 globally by Capterra/Gartner. Before that, as CDO/CTO at a global health brand, I owned email and CRM infrastructure across the US, Europe and Israel. I have spent 15+ years operating sender systems at scale - not only writing campaigns, but managing the infrastructure behind them: authentication, DNS, sender reputation, CRM integrations, API delivery, suppressions, tracking, IP strategy and deliverability recovery. WHAT I DON'T DO I do not do generic email marketing, campaign design, social media, paid ads or “make my newsletter look better” work. I focus on deliverability, sender infrastructure, authentication, DNS, ESP setup and remediation. If that is your problem, send me your sending domain, ESP, recent rejection sample, and a short description of what changed. I will give you an initial read and tell you what I would check first.