Director Web Strategy Jobs in Chicago, IL (NOW HIRING)

Mobile has long been at the center of Gametime's success, but web GMV potential isn't fully realized. Today, the levers that drive it — paid search, on-site conversion, SEO, and content — are managed in pieces rather than owned as a single outcome.

We're hiring a Director of Web Growth to change that: to run web the way a GM runs a business, with GMV as the number you're accountable for and every channel and page as a lever you're willing to pull, cut, or reinvent to move it. You'll identify where growth is being left on the table, prioritize the highest-impact opportunities, and partner closely with Product and Engineering to unlock them — not just request changes, but diagnose funnel drop-off yourself and drive the fixes.

This is a new role. You'll manage our paid search function directly, work hands-on with Product on conversion and funnel performance, and stand up net-new capability in SEO and content — likely starting with contractors and agencies rather than a large owned team. You'll report to the VP of Growth, alongside peers running paid social, CRM/lifecycle, and offline/brand media.

• Web-driven GMV and blended contribution economics as your core metric — not the performance of any single channel in isolation.
• Own the comprehensive view of a web customer's total lifecycle, defining and strengthening the funnel to drive customer lifetime value.
• Direct management of our paid search team — strategy, budget allocation, and performance, with enough SEM fluency to coach and push, not necessarily to execute it yourself.
• Hands-on partnership with Product on CRO — analyzing funnel performance and customer behavior, prioritizing a testing roadmap, and pushing site/experience changes that move conversion, not just requesting them.
• An experimentation engine — establishing a rigorous testing culture across landing pages, user flows, and conversion optimization, in partnership with Product and Engineering.
• Building SEO and content capability from the ground up — scoping the opportunity, deciding whether it's an agency, contractor, or eventual hire, and standing up the initial engine.
• Cross-functional input into paid social and CRM where it intersects with the web funnel or GMV mix, without formal ownership of that channel.
• A clear, data-grounded point of view on when web should feed app installs versus stand on its own, with tradeoffs made explicit to leadership.
• Full-funnel economics — blended CAC/LTV, contribution margin, AOV — as the language you use to defend tradeoffs, not channel-level vanity metrics.
• Visibility and operating cadence — building the dashboards, metrics, and business reviews that keep web growth focused on the highest-impact opportunities.

Required

• 8–12 years in growth, web product, ecommerce, or CRO, including 2–3+ years owning a revenue or GMV number that spanned more than one channel.
• Strong web product sense: you can look at a funnel, form a hypothesis about what's broken, and work with Product/Design/Engineering to test and fix it yourself — this is the core muscle of the role.
• Working fluency in paid search — you understand SEM well enough to direct strategy, coach a team, and ask sharp questions, even if you're not the one in the platform day to day.
• Fluency in full-funnel economics — blended CAC/LTV, contribution margin, AOV — as the language you use to make and defend decisions.
• Experience standing up new capability (a channel, a team, a vendor relationship) from a lean or zero starting point.
• A track record of being evaluated on a business outcome rather than a channel KPI.

Bonus

• Background at a marketplace, travel, ecommerce, or inventory/demand-driven business where SEM, SEO, and CRO had to work together against one number.
• Experience managing SEO and/or content through agencies or contractors rather than solely through an owned team.
• A point of view on web-to-app dynamics in a company with both surfaces.
• Formal experimentation program design (prioritization frameworks, testing governance).
• Pricing or promo strategy exposure.
• AI fluency — using AI to accelerate experimentation, testing velocity, or decision-making.

In your first 90 days

• You've audited the web funnel and SEM program, identified the biggest efficiency gaps and growth levers, and have a documented point of view on where to focus.
• You're managing the paid search team independently and have a clear handle on account structure, budget, and performance.
• You've scoped the SEO/content opportunity and have a plan — agency, contractor, or otherwise — to start building it.

In your first year

• Web-driven GMV is growing efficiently, and you can point to specific tradeoffs you made across channels to get there.
• You've run meaningful CRO/experimentation work in partnership with Product that measurably improved conversion.
• SEO/content capability exists where there was none, and is producing early signal.
• You have a clear, evidence-based point of view on the web/app relationship that leadership trusts.

You'll join a small, experienced growth team and report to the VP of Growth, alongside peers running paid social, CRM/lifecycle, and offline media. This is a player-coach role, weighted toward player — you'll manage the paid search team directly, but the CRO and SEO/content work is hands-on. You're building capability more than inheriting it.

• Flexible PTO
• Competitive salary & equity package
• Monthly Gametime credits for any event ($1,200/yr)
• Medical, dental, & vision insurance
• Life insurance and disability benefits
• Diverse Family-forming benefits through Carrot Fertility
• 401k, HSA, pre-tax savings programs
• Company off-sites and meet-ups
• Wellness programs
• Tenure recognition