Director of Demand Generation & Digital Marketing

The Director of Demand Generation & Digital Marketing owns paid, organic, and web demand across Harbor Compliance and its owned companies and brands. This is a build role as much as a scale role: we are evolving from a predominantly sales-led motion into a business that also acquires and expands through self-service and product-led growth, while moving deliberately toward mid-market and up-market customers. You will lead the demand side of that shift, positioning us for a new audience, building the measurement foundation to prove what works, and owning acquisition efficiency as the guardrail on investment. You will work in close partnership with Product Marketing and with Lifecycle & Customer Marketing, who own positioning and the post-acquisition journey respectively. Key Responsibilities Own the demand generation strategy and roadmap across all brands, accountable for qualified pipeline and new ARR growth. Build, lead, and develop a high-performing demand generation team, and own the web estate and conversion surface with the Web Developer as a direct report. Design and execute a testing roadmap (A/B and multivariate) across landing pages, campaigns, and conversion paths to continuously improve funnel performance. Scale qualified pipeline through GEO/SEO strategy, content, and multi-channel demand campaigns across every brand in the portfolio. Partner with Sales leadership to align messaging, targeting, and lead quality with pipeline and conversion objectives, across both sales-led and self-service motions. Own acquisition efficiency across brands and funnels, using LTV-to-CAC as the guardrail on investment decisions, and treat budget as an output of funnel performance rather than a fixed allocation. Establish data-driven reporting standards, translating web analytics and campaign performance into actionable insight for executive stakeholders. Lead the demand side of our shift from sales-led to product-led growth, building self-service acquisition and conversion paths that run alongside the existing sales motion rather than replacing it. Drive the move up-market, designing and executing demand programmes aimed at mid-market and larger customers, a segment the current funnel and positioning do not yet serve. Build the measurement and attribution foundation, establishing reliable tracking, definitions, and reporting standards before optimising against them. Play a pivotal role in pricing and packaging strategy, partnering with Product, Product Marketing, and Finance to shape how we price and how we present pricing in market, then leading the demand-side execution of those changes. Own competitive positioning in paid channels in a fast-moving, easily imitated category, keeping our acquisition defensible and managing to payback discipline. Collaborate closely with Product Marketing on positioning, messaging, and industry-specific conversion paths, ensuring campaign performance feeds back into positioning decisions. Collaborate closely with Lifecycle & Customer Marketing to hand off acquired demand cleanly and to align acquisition targeting with retention and expansion outcomes. Requirements 7+ years of B2B marketing experience leading demand generation across both sales-led and product-led motions. 3+ years of people leadership experience, with a track record of building and developing high-performing marketing teams. Proven experience owning revenue and efficiency metrics (e.g., ARR contribution, CAC) in a high-growth environment. Technical proficiency with marketing automation, CRM platforms (HubSpot preferred), and web analytics tools (e.g., GA4). Demonstrated ability to align marketing programmes with sales objectives, and to build a self-service motion that complements rather than competes with the sales team. Strong track record of diagnosing funnel friction and implementing pragmatic, measurable improvements. Direct experience building or scaling a self-service / product-led acquisition motion inside a company that was previously sales-led. Experience positioning and generating demand for a new audience, including mid-market and enterprise buyers, and building the funnel, content, and channels to reach them. Has contributed materially to pricing and packaging decisions and led the go-to-market execution of a pricing change. Has built or rebuilt a marketing measurement and attribution implementation, not only operated a working one. Experience running demand generation across multiple brands or business units. Skills and Knowledge Advanced understanding of SEO-informed content strategy and its role in pipeline generation. Familiarity with AI-powered outbound tools and workflows (e.g., Clay, Apollo, enrichment/automation platforms). Practical knowledge of conversion-focused UX principles and funnel optimization methodologies. Commercial fluency in pricing, packaging, and monetisation, and how each shapes demand. Understanding of product-led growth mechanics, including self-service onboarding, in-product conversion, and where they hand off to sales. Accommodations: Harbor Compliance is committed to providing any reasonable accommodations for individuals with disabilities within our application and interview process. To request an accommodation due to a disability, please inform your recruiter. Compensation: Harbor Compliance’s base salary range for this role is listed below. Compensation at the time of offer is based on factors such as skill set, experience, qualifications, and work location. Salary is one part of Harbor Compliance’s total compensation package. Other benefits may include health benefits, flexible paid time off, parental leave, fertility and adoption assistance, 401(k), and educational reimbursement. Note that the salary range and benefits apply only to U.S.-based candidates. Pay Transparency Policy Statement Harbor Compliance will not discharge or in any other manner discriminate against employees or applicants because they have inquired about, discussed, or disclosed their own pay or the pay of another employee or applicant. However, employees who have access to the compensation information of other employees or applicants as a part of their essential job functions cannot disclose the pay of other employees or applicants to individuals who do not otherwise have access to compensation information, unless the disclosure is (a) in response to a formal complaint or charge, (b) in furtherance of an investigation, proceeding, hearing, or action, including an investigation conducted by Harbor Compliance, or (c) consistent with Harbor Compliance’s legal duty to furnish information. Equal Opportunity Statement Harbor Compliance is an equal opportunity employer and does not discriminate on the basis of race, gender, sexual orientation, gender identity/expression, national origin, disability, age, genetic information, veteran status, marital status, pregnancy or related condition, or any other basis protected by law. Notice Regarding the Use of Selection Technology Harbor Compliance uses third-party automated tools and skills assessments (such as Testlify and Rippling) to help evaluate job applications and streamline our hiring workflow. These tools assist our recruitment team in reviewing qualification trends and scheduling, but all final employment decisions are made solely by humans on our Talent Success team, and all tools are subject to human oversight. Depending on your location, local laws may grant you specific disclosure rights or the option to request an alternative evaluation process. If you require a reasonable accommodation or wish to opt out of automated assessment steps due to regional regulations, please notify your recruiter. Opting out will not negatively impact your application. 🏆 Great Place to Work® Certified | USA Harbor Compliance is a leading technology platform for entity compliance, helping more than 80,000 businesses and nonprofits manage licensing, tax registration, and legal entity requirements nationwide. Founded in 2012 and recognized repeatedly by the Inc. 5000 and Deloitte Technology Fast 500, we've grown through five strategic acquisitions — and are now backed by a 2026 majority growth investment from Bregal Sagemount to accelerate product, AI, and customer experience. We're a passionate team making compliance simpler and smarter for every organization we serve.