Head of Marketing / VP of Marketing

Screencastify

$165K *
Consumer Technology
Less than 5 years of experience
Job Overview by Ladders

Qualifications

  • Proven experience driving growth in both B2B SaaS and B2C markets.
  • Experience in startup environments with less than 50 employees, leading the marketing function.
  • Hands-on proficiency with AI marketing tools and workflow automation.
  • Demonstrated ability to connect marketing activities with pipeline and revenue generation.
  • Strong go-to-market partnerships, especially with Sales teams.
  • Expertise in product marketing aspects: positioning, messaging, and segmentation.
  • Ability to function as a player-coach, setting strategy and executing it personally.
  • Familiarity with marketing in the Chrome Web Store is a plus.

Responsibilities

  • Own the complete marketing lifecycle for B2B and B2C from strategy to execution.
  • Drive collaboration with Sales to boost pipeline and revenue.
  • Utilize B2C user base to enhance B2B acquisition strategies.
  • Establish effective outbound marketing strategies that convert activity into revenue.
  • Oversee B2C marketing processes including acquisition, retention, and upselling efforts.
  • Implement lifecycle marketing programs to engage users across various channels.
  • Design AI agents for marketing functions such as lead scoring and content personalization.
  • Conduct user research to refine market positioning and messaging.

Benefits

  • Competitive Compensation based on a data-driven strategy.
  • 401(k) plan with matching contributions and Annual Performance Bonus opportunity.
  • Flexible Time Off (FTO) policy to promote work-life balance.
  • Parental Leave to support family bonding after childbirth or adoption.
  • Comprehensive Medical, Dental, and Vision Insurance with a free One Medical membership.
  • Annual Divvy Bike Membership for employees in Chicago.
Full Job Description
About this role

We are evolving from a widely-used screen recorder into an AI-first learning and collaboration platform, and we need a marketing leader who can own the full picture. This role spans B2B and B2C, demand generation and product marketing, and AI-enabled marketing operations. You will report directly to the President, GTM, lead one individual contributor, and be deeply hands-on yourself. The right person sees a lean team plus smart AI tooling as an advantage, not a constraint.
What you'll do:

Go-To-Market & Demand Generation
  • 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.

Requirements
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.
  • Are hands-on 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.
  • Bring 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).


This role is based out of Screencastify's Fulton Market office in Chicago and follows a hybrid schedule with 3 days a week in the office.
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.

Benefits
  • Competitive Compensation. We take a data-driven approach to our compensation strategy so all employees are paid competitively and fairly.
  • 401(k) & Annual Performance Bonus Opportunity. We want to invest in present you and future you, which is why we offer a 401(k) match + Annual Performance Bonus opportunity.
  • Flexible Time Off (FTO) Policy. We recognize that time off to rest and recharge is important. The Flexible Time Off Policy (FTO) is designed for our employees to do just that -- balance work and life while maintaining well-being.
  • Parental Leave. Generous paid time off for parents to bond with the newest addition to their family!
  • Medical, Dental, & Vision Insurance. We offer comprehensive health benefits, including medical, dental, and vision insurance. Plus, all employees receive a free One Medical membership.
  • Divvy Bike Membership. If you're in Chicago, take advantage of an annual Divvy membership -- on us.

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