Head of Paid Marketing in Winnipeg

We help men save their marriages through results-oriented online coaching, often succeeding where traditional counseling falls short.

We are hiring a Head of Paid Marketing to take full ownership of paid client acquisition at an eight-figure men's coaching company and to run a marketing turnaround. Your scope is paid media, conversion, conversion-rate optimization, and email; organic is a separate function you coordinate with, not run. You report to the CEO, work closely with the founder, and the intent is that within your first months you are running this function end to end. You inherit a proven funnel, years of data, and the current team. Find out what actually broke, fix it, raise the standard of everything we produce, and build the team this business needs to scale to the next level.

What You Will Own

• Paid media strategy and results.
• Account structure and testing methodology with our external media-buying partner –– they execute, you direct.
• Scaling and budget doctrine.
• Lead quality end-to-end; stop teaching the algorithm to bring us men who can't afford the program.
• A CPM-reduction program.
• The call on whether and how to expand Google ads, which currently outperforms Meta on ROAS but ad spent has halved compared to 2 years ago.
• You own the forecast –– revenue → calls → cost per qualified call → spend → creative volume –– and rebuild it monthly.
• You allocate budget across Meta, Google/YouTube and Bing.
• Creative and messaging direction–– our biggest gap and your biggest lever.
• You own the flywheel: mine sales calls and best-customer language → turn that language into hooks, angles, and ads → iterate based on which calls actually close.
• You own the avatar architecture –– high-income professionals and the broad market –– and every ad concept ships with a written hypothesis, target avatar, and rationale.
• You watch our ads and VSL the way a prospect would and tell us what they actually make you feel.
• You must be able to write (VSL copy and direct-response copy) and you write it yourself when it matters most; otherwise you brief and direct the copywriters.
• You own the VSL improvements and iterations, creative volume and diversity targets, and final quality control on everything that ships.
• Compliance and account safety.
• Data, tracking, and attribution.
• You own our conversion-event architecture, what we send to each platform and at what quality threshold.
• You decide with our media buyer on how to manage event routing, run our pixel-conditioning strategy including the up-market experiments, and keep one canonical weekly scoreboard with funnel data by stage.
• Funnel and CRO.
• Front end above all: ads, opt-in, VSL, application, booking, confirmation pages.
• Structured split testing from opt-in through sale –– not just top-of-funnel CTR.
• Email.
• You own the email number and the learning loop between email and paid: sequences and broadcasts built from the same angles as the ads, and winning email concepts fed back into the ads pipeline.
• Team leadership.
• You inherit the current team –– copywriters, video editors, production, the external media-buying partner, our senior direct-response marketer, and the growth operations coordinator we are hiring now –– and you own the team from there.
• You design the team this mission needs and recruit A-players into the gaps.
• You also set the standard for this department and hold the team to it: clear expectations, direct feedback, and the harder conversations when someone is not meeting the bar.
• You also own how this department runs day to day: the processes, the production pipeline, and the throughput and quality of our creative and editing output.
• Competitor and market intelligence.
• You regularly watch and analyze competitor ads and VSLs and telling us specifically how to compete in the market better.
• AI-first operation.
• You use Claude and Claude Code daily –– for analysis, research, SOPs, compliance pre-checks –– and you build systems, not just outputs.

What Winning Looks Like

• In 6 months: ROAS is back toward its historical level, revenue growing again, and a marketing department that holds a standard without the founder inside it.
• In 18 months: this business at a scale it has never reached, with you as the person who took it there –– CMO title, profit-share tied to business growth.
• Ran or led marketing for offer(s) doing $1M+/month within the last 18 months –– verifiable.
• Deep high-ticket call-funnel experience –– optimizing to booked call and sale, not to lead.
• Expert Meta media buying with real Andromeda-era fluency –– creative-as-targeting, concept-level testing, pixel conditioning.
• Proven creative and hook direction, with receipts (ads you directed and the numbers behind them).
• Managed a marketing team of 5+ (copywriters, editors, media buyers, social media managers) to a visibly high standard.
• Built or rebuilt marketing processes and lifted the output quality of a creative team (editors, designers, copywriters), not just managed headcount.
• Compliance-sensitive vertical experience: you've operated where an account can die overnight.
• Nice to have: Google Ads at expert level (strong working competence is preferred).
• Experience in a relationship, men's transformation, or adjacent emotional-transformation niche, and specific concepts you'd test for a marriage offer.
• Hyros, GoHighLevel, ClickFunnels fluency; split-testing tooling that tracks from opt-in to sale (like convert.com).
• An entrepreneurial or intrapreneurial background.

This Is for You If

• You are hypothesis and data driven, you challenge conclusions, including ours.
• Your bar for "good enough" is higher than most.
• You act like an owner: proactive, fast, driving the agenda.
• You work as much as it takes to win and achieve goals, and you take pride in your work; you are not looking for 9-5 type of job with strict hours.
• You study the best in the game and bring it back to the team.
• You think in full funnels and flag bottlenecks wherever they sit.
• You want to work closely with the founder, and keep people informed without being chased.
• You deeply understand our customer: the married man whose marriage is in crisis.
• You own outcomes, not hours.
• You are relentless about growth: you measure everything, you are never satisfied with the current number, and you bring us the next test before we ask for it.
• You address performance problems directly rather than working around them, and you are comfortable rebuilding a team and its processes to reach the standard the business needs.

And Not If

• You want a business that just needs maintaining.
• You do not want to get your hands dirty, and you want to delegate everything to the team.
• Have no creative judgment beyond a dashboard.
• Want to keep other clients on the side.
• Measure your contribution in hours worked rather than results produced.
• Avoid difficult conversations about performance.

Compensation, Structure & Process

• Competitive and above-market six-figure base + significant performance compensation fully tied to performance.
• Fully remote position. Core hours in a European or Dubai time zone.
• Annual bonus of up to 10% of your fee, tied to targets fully within your control.
• Software and AI tools (Claude, ChatGPT, and similar) paid for by the company.
• You won't just fill a role; you'll build the systems and processes.