Director, Demand Generation

RethinkFirst • Chicago, IL

1d • Remote

About The Position

RethinkFirst is a multi-LOB B2B SaaS platform serving behavioral health providers, employers, and K–12 school districts through three business units: RethinkBH, RethinkCare, and RethinkEd. We are building a demand generation function from the ground up with a single mandate: own marketing-sourced pipeline and its contribution to bookings across every line of business.

The Role
We are hiring a Director of Demand Generation to lead the strategy, execution, and team responsible for marketing-sourced pipeline across all three RethinkFirst business units. This is a player-coach role. You will manage a team of Demand Generation Managers (one per LOB), set cross-LOB strategy, and get into the work alongside them when needed. You will own a pipeline number, report against it, and be accountable for marketing’s contribution to revenue.
The challenge here is real. Our LOBs operate across fundamentally different buyer motions: SMB and mid-market clinics with fast transactional cycles in BH, mid-market and enterprise employers with multi-stakeholder procurement in Care, and K–12 school districts with long, policy-driven buying cycles in Ed. You need fluency across all three. Not theoretical understanding. Actual experience running demand gen programs that produce pipeline in fast-velocity SMB environments and in 6-to-12-month enterprise and public-sector sales cycles.

Requirements

• 7 to 10+ years of progressive experience in B2B demand generation, with at least 3 years directly managing and developing a demand gen team.
• Demonstrated experience operating across SMB, mid-market, and enterprise segments with meaningfully different sales cycles, buyer personas, and go-to-market motions.
• A track record of owning a marketing-sourced pipeline number and delivering measurable revenue impact in a scaled SaaS environment.
• Strong analytical ability. You can interpret funnel data, diagnose conversion issues, forecast pipeline health, and build action plans grounded in actual numbers.
• Deep experience with digital advertising, ABM, campaign management, SEO/AEO, and performance optimization across paid and organic channels.
• Hands-on experience with the marketing and sales technology stack: HubSpot, Salesforce, 6sense, ZoomInfo, Clay, Google Ads, LinkedIn, Meta.
• An AI-first mindset with demonstrated experience building agentic workflows and using AI tools to accelerate marketing operations, content production, and decision-making.
• Experience managing external agency and vendor relationships with direct accountability for output quality and ROI.
• Comfort operating in a PE-backed environment where speed, cost discipline, and accountability to pipeline and revenue targets are non-negotiable.

Nice To Haves

• Fluency across SMB, mid-market, and enterprise buyer motions, not just theoretical understanding.
• Actual experience running demand gen programs that produce pipeline in fast-velocity SMB environments and in 6-to-12-month enterprise and public-sector sales cycles.

Responsibilities

• Own 100% of marketing-sourced pipeline across BH, Care, and Ed.
• Set and manage pipeline targets by LOB, allocate budget across channels and segments, and report on marketing’s contribution to bookings.
• Manage and develop a team of three Demand Generation Managers, each responsible for their respective LOB.
• Set clear performance expectations tied to pipeline output, coach on playbook development and execution, identify skill gaps and build development plans, and raise overall team capability as the function matures.
• Build and scale multi-channel demand programs spanning paid search, paid social, display, ABM, email nurture, webinars, events, and thought-leadership content.
• Determine which playbooks apply where, adapt channel strategy to each LOB’s buyer motion and sales cycle, and sequence campaigns to deliver consistent pipeline rather than spike-dependent results.
• Serve as the primary marketing point of contact for paid media, ABM, and creative agency partners.
• Guide strategy, review performance, negotiate scope, and hold agencies accountable for output quality and ROI.
• Track and optimize full-funnel metrics (MAL, MQL, SAL, SQL, Opportunity, Pipeline, ARR) across all three LOBs.
• Interpret data, surface root causes behind performance trends, identify funnel bottlenecks, and build action plans.
• Partner with Marketing Operations to ensure clean multi-touch attribution, accurate reporting, and a reliable data foundation for investment decisions.
• Partner with Sales leadership across all three LOBs to define funnel stages, establish shared handoff criteria, align on lead scoring and routing logic, and build structured feedback loops that improve lead quality and campaign effectiveness over time.
• Own the organic growth strategy, including SEO and AI engine optimization, to expand discoverability across traditional search and AI-generated results.
• Drive conversion rate optimization across landing pages, forms, and key funnel conversion points to maximize lead-to-demo and demo-to-pipeline rates.

Benefits

• Generous health, dental, & vision benefits package
• Flexible paid time off
• 11 paid company holidays
• 401k + matching
• Parental leave
• Access to our award-winning RethinkCare platform supporting neurodiversity in the workplace through parental success, professional resilience, and personal wellbeing.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed