TellMyTale is a custom storybook brand where every child becomes the hero of their own adventure — their name, their face, their story, illustrated and shipped to homes around the world. Parents cry when they read it. Kids ask for the next one. We’re founder‑owned, profitable, bootstrapped, and on path to 8‑figures annually. Think Brave Books — but personalized for every kid, with a monthly subscription product we’re about to build from zero. Role Description This is a founding seat. We’re hiring our first Head of Retention to build the entire retention engine from scratch — most importantly, our monthly book subscription product. The acquisition engine works. Books are flying out. What we don’t have yet is the system that turns one storybook into a tradition: a book a month, growing with the child, becoming the thing every family looks forward to. That system is yours to build. Strategy, tech stack, product design, lifecycle flows, cohort analysis — all of it. Working directly with the founder, with budget and runway to get it right. What You’ll Own The monthly book subscription product — build it, launch it, scale it Email + SMS strategy from scratch (Klaviyo, Attentive, or your call) Post‑purchase, repeat‑purchase, and win‑back flows Repeat gifting flows for parents, grandparents, and gift buyers The roadmap for new retention products as we scale What We’re Looking For You’ve built retention from zero at a DTC brand (subscription experience strongly preferred) You think in cohorts and LTV, not open rates You’ve shipped a subscription product or scaled one You move fast, ship, and learn faster You want to own a function, not a corner of one What We Offer Competitive base + uncapped performance bonus tied to retention growth Free advisory access to operators behind some of the biggest DTC brands of the last 5 years (Everyday Dose and others) — you get their playbooks, their network, their ear Direct access to the founder — no layers, no politics The chance to build something families will remember forever If you’ve built retention from zero at a DTC brand and want to do it again on a product people actually love, DM us. #J-18808-Ljbffr