🟥 EMPLOYERS: Separate from recruiting, I write investment‑grade recruiting briefs that walk A‑player ecommerce candidates through the real business case for your role – the market, channels, KPIs, tech stack, team, and AI issues – before they ever get on Zoom with you. I research / write it. YOU bless it. YOU own it.

RESULT: Your first‑round conversations are with 6-8 highly informed A-players who already understand where/how they can drive EBITDA. To have me write and send your posting out to this list, text Harry Joiner at (404) 281‑2025. Confidential briefs / application process are no problem. ⬇️ SEE EXAMPLE ⬇️

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TODAY’S BRIEF: In 2017, a guy from Cleveland, Ohio started making YouTube videos about watches. Not sponsored content. Not paid advertorials. Just honest, well-researched reviews and explainers about what makes a good timepiece and why.

He built editorial independence by refusing brand money — and that constraint became his most powerful competitive advantage. By the time he launched an ecommerce retail operation around 2020, he had millions of viewers who already trusted him the way you’d trust a knowledgeable friend, not a commissioned salesperson.

Today, Teddy Baldassarre (BALL-de-zar) is a 51–200 person omnichannel brand with a Shopify-powered ecommerce store, a newly expanded 4x-larger flagship boutique in Ohio, and a content engine that reaches 5 to 8 million viewers every single month.

The company is an authorized retailer of over 40 of the world’s most respected watch brands — TUDOR, OMEGA, Breitling, Blancpain, Grand Seiko, IWC, Glashütte Original, Longines, Zenith, NOMOS, Hamilton, Tissot, and more. That means customers get full manufacturer warranties, genuine product, and direct brand support.

This is not a grey-market dealer. This is the real thing.

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Okay, I say this as a card-carrying watch nerd: The overall Swiss luxury watch market is seeing declining volumes. The latest Morgan Stanley report confirms it — fewer luxury Swiss watches are being sold globally, and a handful of “shadow brands” (Rolex, Cartier, Patek Philippe, Audemars Piguet) are consolidating a growing share of a contracting market.

Having said that, the value-to-luxury segment — watches priced from $1,000 to $7,000 — is actually growing. Brands like Frédérique Constant, Christopher Ward, TUDOR, and Longines have been gaining share even as the broader market contracts.

And that is exactly where Teddy Baldassarre’s portfolio is concentrated. The global luxury watch market is projected to grow from $46.3 billion in 2024 to $77.3 billion by 2033 at a 5.08% CAGR, with ecommerce as the fastest-growing channel at an expected 8% CAGR through 2033.

Teddy’s business model is elegantly simple: Create the best free watch content on the internet → build a massive global audience of passionate watch enthusiasts → convert that trust into authorized retail sales. As one third-party industry observer put it: “His YouTube was never at the center of the business model. His YouTube is a funnel to send people to his primary source of income, which is selling watches.”

🟥 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™

The company’s content investment is enormous — a seven-figure annual operation with a large production staff, a permanent studio, scriptwriters, editors, B-roll shooters, and community moderators. But this is not a marketing expense. It IS the marketing. The content budget replaces the paid media budget entirely.

YouTube drives 96% of the company’s social traffic. The website’s blog outranks major publications like Men’s Health and British GQ for high-value watch keywords. Customer acquisition cost is structurally lower than any paid-media-dependent competitor in the category.

So who is the customer? Primarily men aged 25–45 with disposable income, discovering watches through digital content rather than traditional jewelry stores. The sweet spot is the educated, value-driven buyer in the $1,500–$5,000 range who researches extensively before purchasing.

There’s also a meaningful gift-buyer segment — spouses and parents who trust Teddy’s curation precisely because they don’t know enough to curate for themselves. These customers arrive pre-educated and pre-sold after watching hours of content. By the time they click “add to cart,” the trust is already built.

The company has sold over 75,000 watches since launching retail. It’s been profitable and growing at 50–100% annually. No outside debt. The flagship boutique just expanded to four times its original size. And the email/SMS database — which is the single most important revenue lever for whoever takes this job — has barely been built relative to the size of the audience.

That last point is the reason this role exists.

There are somewhere between 5 and 8 million people watching Teddy’s content every month. Only a fraction of them are on the email list. In luxury watch ecommerce, conversion rates are the lowest of any category — typically 0.9% to 1.19%. Average order value is $1,500 to $3,000. Purchase frequency is inherently low because watches are not toothpaste — even an avid collector buys maybe 1 to 3 watches per year.

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That means the entire economic engine of this business depends on the VP of Marketing & Ecommerce building and operating a world-class lifecycle marketing machine that captures viewers at intent moments, nurtures them through the consideration cycle, converts them into first-time buyers, and then engineers reasons for collectors to come back sooner and spend more per visit.

ABOUT THE ROLE

Teddy Baldassarre is seeking a Vice President of Marketing & Ecommerce to lead and scale the company’s marketing and digital commerce growth across a content-led luxury watch ecosystem reaching millions of monthly viewers. Your mission will be to …

• ✅ Build and operate the email/SMS lifecycle marketing engine that converts Teddy’s massive content audience into buyers and repeat customers.
• ✅ Own the website feature roadmap, site merchandising, and conversion rate optimization on Shopify.
• ✅ Drive measurable, profitable revenue growth from marketing channels while protecting the editorial independence that makes the entire business model work.

THIS IS NOT a traditional paid-media marketing role — Teddy’s acquisition is almost entirely organic and content-driven. The VP’s leverage comes from lifecycle marketing, CRO, and audience monetization, not ad spend.

Areas of Oversight

Email & SMS Lifecycle Marketing

• Lead strategy for growing Teddy Baldassarre’s email and SMS marketing database — converting a fraction of 5–8 million monthly content viewers into contactable leads through optimized capture points at intent moments (product page views, blog reads, YouTube click-throughs, back-in-stock requests).
• Architect and optimize the full Klaviyo flow ecosystem: welcome sequence (7-email series with daily touches during peak intent window), abandoned cart flows segmented by prospect vs. existing customer, post-purchase education and cross-sell sequences, win-back flows for lapsed collectors, and seasonal gifting campaigns tied to Father’s Day, graduations, anniversaries, and Q4 holidays.
• Deploy founder-voice email content as a primary conversion lever — research consistently shows that emails from a trusted individual outperform product-focused promotional emails in high-consideration categories, and Teddy’s brand is built on exactly this kind of personal trust.
• Engineer “manufactured moments” to increase purchase frequency against the natural 1–3 year repurchase cycle for luxury watches: new brand launch events, limited-edition drops, collector milestone programs, back-in-stock alerts, and curated “next watch” recommendation flows based on purchase history and browsing behavior.
• Own email deliverability, list hygiene, segmentation strategy, and send cadence optimization — balancing revenue-driving frequency against unsubscribe risk in a luxury audience that values exclusivity and restraint over promotional noise.

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Website Strategy & Conversion Rate Optimization

• Own the website feature roadmap in partnership with the Product Manager — prioritizing Shopify development work that drives measurable conversion rate improvement in a category where the baseline is 0.9–1.19%.
• Manage site organization, merchandising, and product presentation to optimize the purchase journey from product discovery through checkout — with specific attention to visual hierarchy, navigation architecture, and social proof placement above the fold.
• Leverage existing Hotjar and Crazy Egg installations to run heatmap, scroll map, and session recording analysis — identifying the friction points that cause 98%+ of visitors to leave without buying and building a hypothesis-driven testing roadmap to systematically reduce that leakage.
• Optimize the desktop shopping experience for outsized returns — in luxury ecommerce, desktop users convert at roughly double the rate of mobile users despite representing a minority of traffic, making desktop CRO a disproportionately high-leverage investment.
• Ensure timely website content updates including product launches, editorial content integration from the YouTube/blog ecosystem, and brand partner catalog changes as the authorized portfolio evolves.

Marketing Technology & CRM

• Oversee the marketing technology stack (Klaviyo, Hotjar, Crazy Egg, OptinMonster, Shopify) and evaluate where the current starter-level infrastructure needs to mature to support a $20M–$35M revenue business — including advanced segmentation, predictive analytics, customer data platform integration, and attribution modeling across the YouTube → SEO → email → purchase journey.
• Develop tools and processes to support sales enablement for the boutique retail operation — ensuring the flagship store team has access to customer purchase history, wish list data, and lifecycle stage information to deliver a unified omnichannel experience.
• Solve the attribution challenge unique to content-led businesses: the primary acquisition channel (YouTube) does not hand off clean UTM data to the ecommerce funnel, creating a measurement gap between content investment and revenue generation. Building a defensible attribution model for this funnel is a genuine competitive advantage.

Brand Portfolio & Revenue Growth

• Drive measurable growth in revenue generated from marketing channels — owning the connection between audience attention (content) and revenue conversion (ecommerce) as the bridge between Teddy’s content engine and the retail business.
• Monitor brand-partner health within the authorized portfolio — understanding that macro watch market dynamics (declining Swiss volumes, Omega’s multi-year contraction, value-segment growth) directly impact revenue mix and require proactive portfolio emphasis shifts toward growing brands without alienating existing customer segments.
• Collaborate cross-functionally with the content team, brand partnerships, and boutique operations to maintain the editorial independence that is the company’s most valuable and most fragile strategic asset. Any marketing initiative that compromises the audience’s trust in Teddy’s impartiality undermines the entire business model.

🟥 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™

Team Leadership

• Manage and develop a direct team of three: Director of Marketing, Product Manager, and Site Marketing Manager — building their capabilities while maintaining the entrepreneurial speed and decision-making agility the company’s culture demands.
• Determine where to add headcount vs. where to leverage agencies, freelancers, or AI-powered automation to extend the team’s capacity without adding fixed cost disproportionate to revenue.
• Lead through both direct authority and cross-functional influence — the content production team, boutique retail staff, and brand partnership managers are not direct reports but must be aligned with the marketing strategy to execute effectively.

Qualifications

Education & Certification

• Bachelor’s degree in marketing, business, communications, or a related field — or equivalent professional experience that demonstrates the same depth of knowledge.

Functional Competencies — Skills, Knowledge & Experience

• 8+ years of progressive marketing leadership experience with at least 3 years at the Director or VP level, with direct P&L or revenue accountability.
• Deep, hands-on experience with email and SMS lifecycle marketing at scale — ideally on Klaviyo — including flow architecture, segmentation strategy, deliverability management, and measurable revenue attribution from lifecycle programs.
• Proven track record of building and optimizing ecommerce operations on Shopify, including site merchandising, product presentation, conversion rate optimization, and A/B testing programs.
• Experience in high-AOV, low-frequency ecommerce categories (luxury goods, jewelry, fine watches, premium home, specialty retail) where purchase cycles are measured in months or years, not days. You understand that the marketing challenge is fundamentally different when the customer buys once or twice a year at $2,000+ per transaction.
• Strong CRO and analytics fluency — comfortable with heatmaps, session recordings, funnel analysis, and hypothesis-driven testing frameworks. You don’t just read dashboards; you know which questions to ask the data and how to design tests that generate actionable answers.
• Experience with content-led or organic-first acquisition models is strongly preferred. You understand how to monetize an existing audience through lifecycle marketing rather than relying on paid media to generate demand. If you’ve worked with a brand where YouTube, SEO, or editorial content was the primary acquisition channel, that experience is directly transferable.
• Familiarity with marketing technology evaluation and implementation — you’ve outgrown a starter martech stack before and know how to build the business case for upgrading segmentation, analytics, and attribution tooling.
• Nice-to-have: Experience with luxury brand dynamics, authorized dealer relationships, or multi-brand retail assortment strategy. Understanding how brand-partner health affects revenue mix is a differentiator for this role.
• Nice-to-have: AI fluency applied to marketing operations — not as a buzzword, but as a practical toolkit for automating segmentation, generating content variations, building predictive models, and scaling a small team’s output. The question isn’t whether you use AI tools; it’s whether you can articulate how AI makes your marketing measurably better.

Leadership & Management Competencies

• Demonstrated ability to lead and scale a small marketing team (3–5 direct reports) in a high-growth, entrepreneurial environment where the VP is expected to be both strategist and executor — not just a meeting-attender.
• Experience managing cross-functional relationships with content, product, retail, and brand partnership teams — influencing outcomes without direct authority.
• Comfort operating in a founder-led organization where the founder’s personal brand is the company’s primary asset. You know how to build marketing systems that amplify a founder’s voice without trying to replace it.
• Strong vendor and agency management skills — ability to evaluate, onboard, and hold accountable external partners for design, development, analytics, or channel-specific execution.

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Personal Characteristics

• High integrity and intellectual honesty — you tell the truth about what’s working and what isn’t, even when the data is inconvenient.
• Genuine curiosity about the customer and the product category — you don’t need to be a watch collector, but you need to find this audience and this market interesting enough to develop real empathy for how they think and buy.
• Self-directed and resourceful — you don’t wait to be told what to do. You see the gap between where the business is and where it should be, and you build the roadmap to close it.
• Analytically rigorous but commercially intuitive — you can build a financial model for a lifecycle marketing program AND explain to the founder why it matters in plain English.
• Entrepreneurial orientation — you’re energized by building systems from scratch, not just optimizing what someone else already built.
• Resilient under ambiguity — you can operate effectively in a fast-growing company where not every process is documented, not every question has an answer, and not every decision can wait for perfect data.
• Strong written and verbal communicator — marketing leadership in a content-led brand requires someone who can write clearly, present persuasively, and collaborate across functions without creating friction.
• Protective of brand equity — you instinctively understand that short-term promotional revenue is never worth long-term trust erosion, especially in a business built entirely on editorial credibility.

🟥 EMPLOYERS: Separate from recruiting, I write investment‑grade recruiting briefs that walk A‑player ecommerce candidates through the real business case for your role – the market, channels, KPIs, tech stack, team, and AI issues – before they ever get on Zoom with you. I research / write it. YOU bless it. YOU own it.

RESULT: Your first‑round conversations are with 6-8 highly informed A-players who already understand where/how they can drive EBITDA. To have me write and send your posting out to this list, text Harry Joiner at (404) 281‑2025. Confidential briefs / application process are no problem.