Head of Marketing

Rockstar is recruiting for a company that empowers frontline workers by providing a real-time feedback platform to help companies reduce turnover, improve engagement, and build stronger relationships with their workforce. The client's mission is to create a more connected and human-centered workplace by ensuring employees’ voices are heard and acted upon. They are at a pivotal moment—having achieved initial product-market fit, they are now refining their go-to-market (GTM) strategy to accelerate adoption and improve customer retention. They need a scrappy, data-driven, and customer-obsessed Head of Marketing to own and execute their marketing strategy, aligning with broader growth and product objectives.

Company Overview

At this company, frontline workers are empowered by providing a real-time feedback platform that helps companies reduce turnover, improve engagement, and build stronger relationships with their workforce. The mission is to create a more connected and human-centered workplace by ensuring employees’ voices are heard and acted upon. They are at a pivotal moment—having achieved initial product-market fit, they are now refining their go-to-market (GTM) strategy to accelerate adoption and improve customer retention. A scrappy, data-driven, and customer-obsessed Head of Marketing is needed to own and execute the marketing strategy, aligning with broader growth and product objectives.

Position Overview

As the very hands-on Head of Marketing, this individual will lead the company’s marketing efforts as an independent contributor, focusing on refining positioning & messaging, designing & testing new GTM strategies, and driving demand generation of Truckers, Private Fleets, and Trucking Logistics Enterprises. This person will work closely and cross-functionally with the CEO (serving as a thought partner and leader), Revenue Operations, an Account Executive, Product & Engineering team, Customer Success, and other contractors to craft and execute strategies that revalidate the ideal customer profile (ICP), improve retention, and generate high-intent leads. This role is perfect for a hands-on marketer who measures their impact, thrives in ambiguity, has growth experience guiding B2B SaaS or HR Tech prospects through the top of the funnel, and loves balancing strategic positioning, demand generation, and retention marketing, as they scale experiments into channel strategies.

What You’ll Do

In the first 3 months, this individual will:

- Deeply understand the existing customer base, pain points, and retention drivers.

- Audit current messaging and marketing efforts, identifying gaps and opportunities.

- Test and refine positioning to better resonate with high-intent buyers in the market.

- Launch rapid GTM experiments across digital, outbound, and community-driven channels.

In the first 6 months, this individual will:

- Optimize demand generation through targeted multi-channel campaigns (email, outbound, paid, partnerships).

- Improve sales-marketing alignment, ensuring marketing efforts drive qualified leads that convert into long-term customers.

- Support retention marketing by creating content, campaigns, and touchpoints that reduce churn.

- Define and measure key KPIs such as pipeline contribution, conversion rates, and CAC/LTV.

In the first year, this individual will:

- Establish a scalable and repeatable marketing playbook based on data-backed insights.

- Lead market repositioning if necessary, ensuring the company stays competitive and relevant in the space.

- Build and execute a customer advocacy strategy, using case studies and referrals to fuel growth.

- Experiment with new growth channels and optimize spend based on what delivers results.

Who You Are

- Customer-Obsessed: Loves talking to customers, understanding their needs, and translating insights into impactful marketing.

- Scrappy & Experimental: Moves fast, runs small tests, and quickly doubles down on what works.

- Full-Stack Marketer: Has experience across demand generation, content marketing, outbound, and customer engagement.

- Data-Driven & Results-Oriented: Knows how to measure success and optimize marketing based on performance.

- Team Player: Works seamlessly with Sales, Customer Success, and Product teams to drive impact.

What You Bring

- 5+ years of B2B SaaS or HR Tech marketing experience, ideally in a high-growth or startup environment.

- Proven ability to reposition a product and refine messaging to address shifting market needs.

- Track record of demand generation success, including campaign execution, SEO, outbound, and paid media.

- Experience working on retention marketing or churn reduction strategies (preferred).

- Ability to translate customer insights into compelling messaging and GTM strategies.

- Comfort working in a fast-moving, small-team environment where strategy and execution are owned.