Apply Now Sleepyhead
SCOTTSDALE, AZ — With more than 200 digital commerce jobs each year, EcommerceRecruiter.com is the leading contingency-based executive search firm serving the DTC, B2B, and private equity communities. To opt-in to our popular “Ecommerce Job of the Day” email, click here. (Simply unsubscribe at the end of your job search.)
I’m a contingency recruiter who researches and writes job postings that do the selling for you. That’s been my jam for 15 years. If you are an employer looking to post a job on this site, please text Harry Joiner at 404-281-2025. If you need help recruiting, I’d love to be of assistance there, too!.
HARRY’S COMMENTS Sleepyhead was born in 2016 when its founder, Steven Van Alen, was a college student who couldn’t sleep on his terrible dorm mattress. He entered a university business competition with the idea for a premium, student-focused mattress topper brand, won first place and $20,000 in seed money, and started building.
Sleepyhead ranked #213 on the 2025 Inc. 5000 list of America’s fastest-growing private companies, with 1,789% revenue growth from 2021 to 2024. They’re #5 in Retail nationally and #5 in Arizona. This is now an 8-figure DTC brand running on Shopify, and it’s still accelerating.
The global mattress topper market was valued at roughly $6.5–7 billion in 2024 and is growing at 3–5% annually. The US mattress market alone runs $10–18 billion depending on how you scope it. But those broad numbers miss the real story for Sleepyhead: every year, roughly 20 million students are enrolled in American colleges.
Back-to-college spending exceeds $90 billion annually. And the Twin XL mattress — the standard dorm bed — is famously thin, firm, and miserable. Parents are willing to spend $300–400 to fix that problem for their kid. Multiply anxious parents by uncomfortable dorm beds across thousands of campuses and you’ve got a niche that generates serious revenue for the brand that owns it.
And Sleepyhead owns it.
The Sleep Foundation ranks them #1 for college dorm toppers with an 8.9 out of 10 test score. They’ve been covered by CNN, Inc., Tom’s Guide, and Arizona Foothills. YouTuber Ryan Trahan gave them a shoutout in a viral video series. They sell premium gel and copper-infused memory foam toppers with CertiPUR-US certification, removable washable covers, and a “good-till-graduation” warranty. Their products are available on their own Shopify storefront, Amazon, Walmart.com, and Urban Outfitters.
Sleepyhead’s customer isn’t one person — it’s two people. Mom pays; the student sleeps. That means this Director of E-Commerce is building two parallel funnels, not one. Parent messaging is about safety, warranty, value, and “my kid will actually sleep.”
Student messaging is about comfort, lifestyle, and social proof from peers. Ad targeting, email segmentation, review strategy, and landing page architecture all have to account for this split — and if you’ve run DTC acquisition funnels before, you know that’s a much more interesting problem to solve than just “sell more stuff.”
The founder, Van Alen, comes from the ecommerce and digital growth world. He’s built the company working with high-end Shopify experts from the Storetasker ecosystem — the same talent network that serves brands like Warby Parker and Casper. This isn’t a company that views ecommerce as a side channel. Shopify is the operating system for the entire business.
ABOUT THE ROLE
Sleepyhead is hiring a Director of Ecommerce to help scale the next phase of growth for an Inc. 5000-ranked, 8-figure DTC brand built on Shopify. Your mission will be to 1.) increase conversion rate and AOV across the Shopify storefront through structured CRO testing, bundling, and checkout optimization; 2.) build and optimize Klaviyo and Postscript lifecycle marketing flows that drive measurable LTV and repeat purchase revenue; and 3.) improve Amazon Seller Central performance while protecting contribution margin.
THIS IS NOT A MAINTENANCE ROLE — this is a builder role in a company still being built, and the expectation is that you will own outcomes, not tasks.
Areas of Oversight
Shopify Storefront & Conversion Rate Optimization
1./ Own the full Shopify customer journey from ad click to order confirmation, with a specific mandate to increase conversion rate on both mobile and desktop. This means auditing the current funnel by device and traffic source, identifying where visitors drop off, and running structured A/B tests on PDP elements including hero images, size selectors, social proof placement, guarantee blocks, and price anchoring against competitors.
2./ Use Shopify Online Store 2.0 sections, metafields, and templates to build and iterate on landing pages that match paid media ad promises — particularly for Meta and Google campaigns targeting back-to-college keywords. The expectation is that you can direct external Shopify specialists while also making changes yourself; waiting on agencies for every storefront update is too slow for a brand this seasonal.
3./ Optimize the mobile checkout experience using Shopify Checkout Extensibility — including trust badges, progress bars, digital wallet configuration (Shop Pay, Apple Pay, Google Pay, Amazon Pay), and post-purchase offer blocks. If you’re still thinking in terms of editing checkout.liquid, this isn’t the right fit.
🟥 JOB SEARCH GOT YOU STUCK? Book an hour with VP/CMO ecommerce recruiter, Harry Joiner, who prepared this analysis. Includes a 3-month membership to NEXTgig™
4./ Maintain site speed and stability while experimenting. There is a real trade-off between adding apps and maintaining checkout reliability, and this Director needs to manage that tension deliberately, especially during peak season when every second of load time costs conversions.
Bundling, AOV, & Revenue Monetization
5./ Launch structured bedding bundles on Shopify — “Dorm Comfort Bundle” (topper + protector + pillow) at 10–15% savings, “Ultimate Sleep Bundle” at 15–20% — mirroring the tiered bundle strategies proven at brands like Brooklinen and Casper. Each bundle should have a clear price anchor showing value vs. buying separately.
6./ Implement pre-purchase upsells and cross-sells on PDP and cart pages (pillow/protector add-ons, thickness upgrades), post-purchase one-click offers via checkout extensions, and threshold-based incentives (e.g., “Add $40 more for free shipping”) to systematically lift AOV from the current estimated ~$375 range.
7./ Build “buy-more-save-more” mechanics for sibling and multi-room buyers — 2 toppers save 10%, 3+ save 15% — using quantity break logic on key Twin XL SKUs. The college topper market has a natural multi-buy dynamic (siblings, friends) that most brands in this space aren’t exploiting.
8./ Guard pricing discipline. Every discount erodes the premium positioning that justifies 2.5× pricing over competitors like Viscosoft. Bundle discounts should be smaller than site-wide promos, and deep discounting should be limited to short, defined bursts (BFCM, back-to-college launch).
Klaviyo & Postscript Lifecycle Marketing
9./ Architect and oversee the full Klaviyo flow stack: welcome series, browse abandonment, abandoned cart/checkout recovery, post-purchase education and setup guidance, accessory cross-sell, sibling/win-back, VIP/referral, back-in-stock, price drop alerts, and a dorm move-in countdown flow tied to calendar-based urgency.
10./ Segment flows by buyer type. Parents (identified by billing/shipping name mismatch or non-.edu email) should receive warranty, value, and reassurance messaging. Students (identified by .edu email or self-purchase indicators) should receive comfort, lifestyle, and peer social proof messaging. This “two-customer” segmentation is non-negotiable for a brand where the buyer and user are different people.
11./ Time post-purchase flows to real bedding behavior: setup and care tips within 1–2 days of delivery, review requests at 14–21 days (after they’ve actually slept on it), accessory cross-sell at 30+ days, and sibling/upgrade outreach at 9–12 months aligned to the next back-to-college cycle.
12./ Hold the email/SMS program accountable to revenue targets: 25–30% of total revenue from email/SMS once mature, with flow revenue comprising roughly half of that. Monitor flow revenue per recipient, list growth rate, and unsubscribe rates to ensure the program scales without burning the list.
Amazon Seller Central & Marketplace Management
13./ Improve listing quality, backend keyword structure, A+ content, and catalog organization on Amazon Seller Central to increase organic rank and conversion rate on the marketplace. Amazon is a discovery channel for parents who search “college mattress topper” — the listing must convert those high-intent shoppers at competitive rates.
14./ Monitor Amazon contribution margin separately from DTC, accounting for referral fees, FBA/FBM fulfillment costs, advertising spend, and return rates. If Amazon isn’t profitable on a standalone basis, the channel strategy needs revisiting.
15./ Coordinate pricing, inventory, and promotional timing between Shopify and Amazon to prevent channel conflict (parents finding lower prices on Amazon) and stockouts during peak season. Inventory synchronization is especially critical during the July–September back-to-college window when demand spikes.
16./ Identify scaling opportunities on Amazon — Sponsored Products, Sponsored Brands, A/B listing experiments — that protect margin while expanding reach. The goal is disciplined marketplace growth, not a race to the bottom on price.
Data, Reporting, & Contribution Margin Accountability
17./ Own the four core KPIs explicitly called out for this role: conversion rate, AOV, ROAS, and contribution margin. These must be reported correctly by channel, by device, by product, and by week — not as blended averages that mask underperformance in key segments.
19./ Build or fix the measurement infrastructure. If Shopify product data, discount logic, shipping rules, and refund handling are configured sloppily, every downstream metric — from Klaviyo flow attribution to paid media ROAS to contribution margin by SKU — becomes fiction. In a fast-growth startup, cleaning the data plumbing is often the highest-ROI work you can do before touching anything else.
20./ Run weekly performance reviews anchored to the four KPIs. Sort the CRO and project backlog by forecasted impact on margin, LTV, or payback speed — not by what feels urgent. The team should be in outcome mode, not task mode.
21./ Feed clean product, order, and customer data to Klaviyo, Postscript, Meta, Google, and Amazon so that each platform optimizes to real purchase signals, not phantom events. Dirty conversion data is the silent killer of paid media efficiency.
🟥 JOB SEARCH GOT YOU STUCK? Book an hour with VP/CMO ecommerce recruiter, Harry Joiner, who prepared this analysis. Includes a 3-month membership to NEXTgig™
Qualifications
EDUCATION & CERTIFICATION
Bachelor’s degree in marketing, business, or a related field, or equivalent professional experience.
FUNCTIONAL COMPETENCIES — SKILLS, KNOWLEDGE & EXPERIENCE
5–8+ years of progressive ecommerce experience, with a demonstrable track record of scaling a DTC brand on Shopify. This is the non-negotiable. If your Shopify experience is limited to basic theme customization, this role is too senior.
Deep working knowledge of Shopify’s architecture: Online Store 2.0, sections, metafields, Checkout Extensibility, product/collection structure, discount logic, and data export. You should be able to diagnose a conversion problem in the Shopify admin without waiting for a developer to explain what’s happening.
Hands-on experience with Klaviyo (required) and Postscript (preferred), including flow architecture, segmentation logic, event triggers, and revenue attribution. You should know the difference between a well-built abandoned cart flow and a default template that’s never been optimized.
Proven experience managing Amazon Seller Central, including listing optimization, keyword strategy, advertising campaigns, and contribution margin analysis. Experience with Walmart Marketplace is a plus.
Strong analytical capability. You live in the numbers — conversion rate, AOV, ROAS, contribution margin, CAC by channel, RPV by traffic source. If you can’t build a weekly dashboard and use it to make real decisions, this isn’t the right role.
Experience with CRO testing methodology — A/B testing, landing page optimization, checkout optimization — with a structured approach to hypothesis, measurement, and iteration. Random tests on the homepage don’t count.
Experience with bundle and upsell strategy in a DTC context. Understanding of how to structure pricing, product groupings, and post-purchase offers to lift AOV without eroding margin.
AI fluency as a practitioner tool. The expectation is that you use AI to execute faster and think sharper — not as a research toy. Tie your AI usage to specific business outcomes: faster creative testing, better segmentation, smarter competitive analysis.
Nice-to-have: Experience in a highly seasonal business where the majority of revenue concentrates in a short window. Experience with bedding, home goods, or other high-AOV / low-frequency DTC categories. Experience managing the parent/student buyer-user dynamic or any business where the purchaser and the end user are different people.
LEADERSHIP & MANAGEMENT / BEHAVIORAL COMPETENCIES
This role reports to the Head of Ecommerce and works closely with the founding team, including the CEO. You must be comfortable operating in a flat, fast-moving organization where decisions happen quickly and ownership is expected, not delegated.
Ability to direct external Shopify specialists, Klaviyo/Postscript agencies, and creative resources. This isn’t a managing-down role with a large direct team — it’s a lead-through-influence role where you set the strategy, define the metrics, and hold outside partners accountable to results.
Cross-functional collaboration with paid media, creative, and customer service. The email/SMS program, the Shopify storefront, the Amazon channel, and the paid acquisition funnel are all interconnected — and this Director needs to see the whole system, not just their own lane.
Comfortable presenting data-driven recommendations to executive leadership and defending your priorities with evidence, not opinions.
🟥 JOB SEARCH GOT YOU STUCK? Book an hour with VP/CMO ecommerce recruiter, Harry Joiner, who prepared this analysis. Includes a 3-month membership to NEXTgig™
PERSONAL CHARACTERISTICS
High integrity. You say what you mean, own your mistakes, and don’t hide bad numbers.
Self-directed. The job posting says it plainly: “You do not need to be managed. You manage outcomes.” That needs to be true, not aspirational.
Highly competitive, with a bias toward action. This is a builder role in a company that grew 1,789% in three years. If you need six months of analysis before making a decision, the seasonal window will pass you by.
Resilient and adaptive. The company is still evolving — the org chart may shift, the competitive landscape will move, and 60%+ of the year’s revenue may compress into 90 days. You thrive in that environment, not despite it, but because of it.
Strong communicator who can translate data into plain-English decisions. You’re equally comfortable presenting a contribution margin analysis to the CEO and explaining a Klaviyo flow logic to a junior team member.
Intellectually curious. You track competitors, read the category data, monitor review rankings, and know what Viscosoft changed on their comparison page last month. You’re the person who always knows what’s happening in the market before anyone asks.
Entrepreneurial orientation. In a company this size, you will encounter problems that don’t have a process yet. You build the process.
You genuinely believe that data wins arguments — and you live that conviction every day.
1./ DISCLAIMER: This blog is for informational purposes only. ALL APPLICANTS ARE APPLYING DIRECTLY TO THESE COMPANIES. THESE ARE NOT MY SEARCHES. Anyone can send me an ecommerce job posting for publication and I will consider adding it with research + insights, similar to the other posts on this site. This is a highly-targeted subscriber list — plus I have 32K Linkedin followers and moderate TWO of the top five Linkedin groups for ecommerce.
2./ ABOUT: My objective with this blog is to give my readers better insight on publicly posted ecommerce jobs so they can be more thoughtful about where / how they apply. All information contained herein was available online. If you know someone who has already applied for this job, send them this write up.
3./ EDITS: If you are currently employed by the company in this posting and you’d like me to make an addition or correction to this write up, that’s NO PROBLEM. Simply text your request to (404) 281-2025, and I’ll call you at my soonest convenience. If you’d like to engage me as a recruiter (20% contingency / 90-day replacement), use THIS LINK to schedule a call.
4./ LINKEDIN: If you’d like to hit me up on LinkedIn, CLICK HERE. Since 2005, I’ve been a very active recruiter for marketing and ecommerce. (Just ask ChatGPT, “Using at least 10 sources from around the web, what can you tell me about ecommerce recruiter, Harry Joiner?”)
5./ SUBSCRIBE: To subscribe to the CMO Job of the Day, CLICK HERE. Simply unsubscribe at the end of your job search.
6./ RESUMES: Jobseekers, if you’d like to send me your latest resume, my email address is Harry.Joiner [at] EcommerceRecruiter [dot] com. I’d love to hear from you.
To apply for this job please visit www.linkedin.com.
