Head of Marketing / VP of Marketing

The right person for this role will lead Castify's marketing efforts, spanning both B2B and B2C, and will oversee the transition from a screen recorder to an AI-first learning and collaboration platform.

About the role

We are looking for a Head of Marketing / VP of Marketing to lead our next stage of growth. This role involves B2B and B2C demand generation, product marketing, and AI-enabled marketing operations. The ideal candidate will see a lean team and smart AI tooling as an advantage, not a constraint.

What you'll do

• Own the full marketing lifecycle across B2B and B2C; strategy through execution.

• Drive pipeline and revenue growth in close partnership with Sales.

• Leverage the B2C user base to fuel B2B acquisition (PLG motion).

• Build a consistent outbound motion and convert marketing activity to closed revenue.

• B2C Business Ownership:

  • Own B2C marketing end-to-end: acquisition, activation, retention, and upsell.

  • Run lifecycle marketing programs (email, in-product, push) to convert free users and reactivate dormant ones.

  • Build community and content strategies to grow organic reach.

  • Track B2C KPIs: MAU, conversion rate, churn, and B2C ARR.

• AI-Enabled Marketing Workflows & Agents:

  • Design and deploy AI agents across marketing functions: content, lead scoring, personalization, SEO, and reporting.

  • Build automated, intelligence-driven programs that scale output without scaling headcount.

  • Stay at the forefront of AI marketing tools and codify workflows on which the team can iterate.

  • Model what AI-first marketing operations look like for the rest of the organization.

• Product Marketing:

  • Own positioning, messaging, and segmentation across all customer segments.

  • Create sales enablement materials, customer-facing content, and internal training resources.

  • Conduct user research to inform go-to-market strategy and surface actionable market insights.

  • Represent Castify at conferences, events, and customer meetings.

• Leadership, Planning & Reporting:

  • Lead and coach one marketing IC while remaining deeply hands-on yourself.

  • Use AI tooling to multiply team capacity, enabling two people to operate like many.

  • Establish KPIs across B2B and B2C and provide regular performance reporting.

  • Work with the executive team on strategic planning and market expansion into new segments.

You're perfect for this role if you:

• Have driven measurable growth across both B2B SaaS and B2C consumer products.

• Have thrived in early-stage or growth-stage startups (under 50 people) where you had responsibility to lead the marketing function.

• Have hands-on experience with AI marketing tools and have deployed agents or automated workflows in a real marketing context.

• Have built demand generation engines that connect marketing activity to pipeline and revenue.

• Have strong GTM partnership experience working closely with Sales.

• Have deep product marketing chops: positioning, messaging, segmentation, and go-to-market execution.

• Are a player-coach who sets strategy and then executes it yourself.

• Have experience marketing in the Chrome Web Store (a plus).

Chicago-based position with 3 days a week in the office

Castify is a results-focused, fast-moving company that values accountability, speed, and people who take ownership end-to-end. We embrace experimentation and the examination of all kinds of ideas through reasoning and testing.

At Castify

We foster an inclusive, supportive, fun, and challenging team environment. We value having a team that is made up of a diverse set of backgrounds and respect the healthy expression of diverse opinions.

Compensation

The expected annual base salary for this role is anticipated to start at $165,000 with an annual performance bonus. Final compensation may vary based on experience and qualifications.