Head of Online Sales & Digital Marketing

Head of Online Sales & Digital Marketing
Lailey Winery · Niagara-on-the-Lake, Ontario · 
Hybrid (onsite or remote with regular winery visits)
Full-time employee or part-time contractor

The role
We're looking for a hands-on digital marketer who can hit the ground running and start driving online sales from the first weeks. This role is dedicated entirely to growing our online sales, with one core measure of success: the dollar value of wine sold through laileywines.com.

You'll quickly map out a rolling campaign plan, then design and launch campaigns across email, Instagram, Google, and paid social to bring buyers to our online store. You'll watch the results daily, double down on what works, and move on to the next campaign. Website improvements happen along the way, as campaigns need them, not as a separate project.

You don't need a background in wine. We need someone who knows how to create online demand and turn it into sales. We'll teach you the wine.

Work arrangement
This role can be based at our winery or done largely remotely, with regular visits to our winery in Niagara-on-the-Lake to capture content, work with the team, and stay close to the wines. We're open to hiring either a full-time employee or a part-time contractor, depending on the right fit.

Your first 90 days

• First 2–3 weeks: Get to know our wines, customers, and online store. Build a rolling campaign calendar for the next 3 months and launch your first campaigns.
• By day 60: Have several campaigns live across email, social, and paid ads, with clear results tracked for each.
• By day 90: Know which channels and offers drive our online sales, and be scaling them with measurable revenue growth.

What you will do

Campaigns and online sales

• Plan and maintain a rolling campaign calendar: new releases, seasonal pushes, holiday gifting, bundles, and limited offers
• Design and launch online campaigns end to end: concept, offer, copy, creative, targeting, and landing page
• Run email campaigns and set up automated emails (welcome, abandoned cart, post-purchase, win-back)
• Use Instagram and social media with a commercial purpose: build an audience that buys
• Run and optimize paid ads on Google (Search and Shopping) and Meta (Instagram and Facebook)
• Track online sales every day and report weekly on revenue, conversion rate, average order value, cost per sale, and return on ad spend
• Test offers, creative, and audiences constantly, and scale what works quickly
• Develop online corporate gifting and custom case sales

Website (as campaigns require)

• Build landing pages and update product pages, collections, and offers on Shopify to support each campaign
• Identify and fix what's slowing down sales on the site, prioritizing quick wins
• Improve search visibility (SEO) over time

Budget and partners

• Manage the digital marketing budget and any freelancers or agencies