About the Role

Gusto is looking for a Paid Social Marketing Lead to own our paid social program end-to-end, from brand awareness through conversion, across social channels such as Meta, LinkedIn, Reddit, and TikTok. This is a high-visibility, high-impact role at the intersection of performance marketing, creative strategy, and AI-powered workflow design. You will serve as the strategic lead for paid acquisition across paid social and adjacent channels, setting the framework for how paid media operates within Gusto's demand generation engine. You'll have full strategic and creative latitude over one of Gusto's most important acquisition channels, with direct influence on pipeline and revenue. If you're a full-funnel paid social operator who thinks in systems, holds creative and data rigor in equal measure, and uses AI as a genuine daily tool, we want to meet you.

About the Team

As a member of Gusto’s Demand Generation team, you will be embedded specifically within Paid Acquisition, a focused group responsible for driving awareness and pipeline through paid media. This team operates with high autonomy, a bias for experimentation, and a culture of cross-functional partnership. We hold ourselves to a high standard, move fast, and genuinely believe that being AI-native is part of what it means to do this job well today.

Here's what you'll do day-to-day:

• Own paid social strategy and execution across Meta, LinkedIn, Reddit, Quora, and TikTok, driving full-funnel campaigns from brand awareness through retargeting and conversion, with accountability to pipeline and revenue targets.
• Manage significant, multi-million dollar budgets with rigor, including campaign pacing, forecasting, budget-vs-actuals analysis, and making the case for paid social investment in imperfect attribution environments.
• Define and socialize Gusto's paid acquisition measurement framework, including attribution philosophy and budget allocation principles, establishing this as the standard for the broader marketing team.
• Lead creative strategy and testing at scale: briefing creative studios and agencies, structuring meaningful experiments, interpreting complex data sets to drive actionable insights, and building a clear learning roadmap.
• Act as Gusto's internal subject matter expert on paid social and AI-powered marketing workflows, developing playbooks and frameworks adopted across the marketing org.
• Partner with Web Marketing to align on landing page strategy, message match, and post-click conversion, because paid social performance doesn't end at the click.
• Manage agencies and contractors, and an IC by setting clear expectations, reviewing quality, and holding partners accountable to results.
• Use AI tools as a consistent, habitual part of your workflow: generating campaign briefs, developing copy variants, accelerating audience research, and building reusable systems that raise the bar for the whole team.
• Collaborate cross-functionally with Integrated Marketing, Communications, and Web to align paid social with integrated campaigns, product launches, and earned media moments, and bring performance data back upstream to influence creative production and asset strategy.

Here's what we're looking for:

• 12+ years of paid social experience or equivalent at a B2B SaaS, performance marketing agency, or high-growth consumer organization.
• Full-funnel ownership across two or more major paid social platforms (Meta, LinkedIn, Reddit, Quora, TikTok) with significant budget responsibility and a track record of driving measurable pipeline impact.
• Demonstrated experience managing external agencies and/or contractors, setting expectations, measuring performance, and holding partners to a high bar.
• Strong creative strategy and testing instincts: you know how to structure a test, distinguish a learning from a result, and translate performance data into creative direction.
• AI-fluent in practice, not just in theory; you use AI tools consistently in your day-to-day workflow to accelerate briefs, copy, and analysis, and have a track record of implementing AI-driven efficiencies for your team.
• Excellent cross-functional collaborator who can translate integrated briefs into paid social strategy, advocate for what the channel needs, and work effectively alongside brand, web, and comms partners.
• You are analytical and data-driven, with a clear point of view on attribution in imperfect measurement environments and comfort communicating paid social's contribution to business outcomes.

Compensation

Our cash compensation amount for this role is $151,020/yr to $180,000/yr in Denver, Phoenix/Scottsdale, Las Vegas, Chicago, and Atlanta, and $177,550/yr to $210,000/yr for San Francisco & New York. The cash compensation range for Toronto is (CAD) $134,285 - $158,000. Final offer amounts are determined by multiple factors including candidate location, experience and expertise, and may vary from the amounts listed above.

Roofr is building the application foundation that will define how AI is integrated across our entire product — and we need someone to make sure it actually works. As our Senior AI Quality Engineer, you'll sit on the AI Platform team and own the eval frameworks, testing standards, and quality gates that every engineering team at Roofr depends on to ship AI with confidence. But this role extends well beyond the platform — you'll work horizontally across the entire testing organization, training teams, embedding best practices, and raising the bar on how Roofr tests everything it builds with AI. This is early, foundational work — you're setting the standard for the whole org, not just one team.

What You'll Get to Do:

• Define the testing standards and patterns for AI at Roofr — establishing how product teams validate AI behaviour when building on top of the application foundation
• Build and own Roofr's LLM eval framework — selecting and extending the right tooling (e.g. Promptfoo, DeepEval, Braintrust) and designing the methodology that measures whether our AI integrations and agent outputs are performing correctly, consistently, and safely
• Integrate quality gates into CI/CD pipelines so that regressions in AI behaviour are caught before they reach production
• Design and implement human-in-the-loop review processes for AI outputs where automated evaluation isn't sufficient
• Embedded on the AI Platform team — ensuring quality is designed into the integration architecture from day one, not bolted on after the fact
• Work horizontally across the testing organization — coaching QA engineers and developers on AI eval patterns, embedding best practices into team workflows, and actively raising the quality bar across engineering
• Stay close to the evolving AI quality landscape — new eval techniques, benchmarking approaches, and tooling like Ragas, Arize Phoenix, or LangSmith — and bring the best of it to Roofr

What You'll Bring to the Role:

• 5–8 years of software engineering or quality assurance experience
• Hands-on experience building eval frameworks for LLM-powered features — you've thought seriously about how to measure output quality, consistency, and regression, and you've worked with tools like Promptfoo, DeepEval, Braintrust, or similar
• Strong engineering fundamentals — you write real code, build real tooling, and aren't reliant on manual testing processes
• Experience integrating automated quality checks into CI/CD pipelines
• Familiarity with LLM APIs and agent frameworks (e.g. Anthropic Claude, OpenAI, or similar) and the specific quality challenges they introduce
• Experience designing human review workflows to complement automated evaluation
• Strong collaboration skills — you'll be working across many teams, and the standards you set only work if engineers actually adopt them
• Comfort operating in an early-stage environment where the right approach isn't always obvious and you'll need to figure it out
• Genuine ownership mentality — you care about whether AI at Roofr works well, not just whether the tests pass

Compensation Range: $140,000 - $160,000 CAD