Head of Marketing

Head of Marketing

About Helpside:

For more than 30 years, we have collaborated with and supported small to medium-sized businesses by providing Payroll, HR, Workers' Compensation, and Benefits solutions. Our goal is to support our clients in such a way that they can continue to grow their businesses and not worry about employee administration.


Role Overview:

We're looking for a player-coach marketing leader to build and lead our marketing function from the ground up. Reporting to the COO, the Head of Marketing will partner closely with sales and operational leadership to develop and execute our go-to-market strategy while building a high-performing team across product marketing, customer marketing/referrals, and demand generation.


What You'll Own in Year One:

1. Build a scalable demand engine. Develop state- and vertical-specific marketing programs that generate qualified pipeline through targeted campaigns, compelling content, optimized landing pages, and outbound initiatives.
2. Accelerate broker channel growth. Create the marketing strategy and enablement programs that help our broker partners succeed, including sales collateral, co-marketing campaigns, and channel enablement.
3. Customer marketing and referrals. Turn satisfied customers into a growth engine through referral programs, case studies, advocacy initiatives, and NPS driven outreach.

Who You Are:

• 8-12+ years in B2B marketing focused on SMB buyers. Services or insurance-adjacent background is a strong plus. PEO experience is welcome but not required.
• You know how to use AI to improve the way you work, not just for chat, but as a tool that helps you move faster and make better decisions.
• You think strategically about markets and industries. You've developed go-to-market strategies for different verticals and understand that messaging needs to be tailored to each audience.
• You're comfortable with the numbers. Pipeline, conversion rates, CAC, LTV, and payback period are familiar territory, and you know how to connect marketing performance to revenue.
• You're a builder, not a framework artist. You launch campaigns, learn from the results, and focus on outcomes over activity.
• You're a partner. You work closely with sales and product, collaborating regularly to align priorities and improve results.
• You're hands-on. You lead by doing - writing copy, building campaigns, and setting the standard through execution.

Who You Are Not:

• You don't solve problems by signing agencies. You build solutions.
• You don't measure marketing in MQLs. You measure it in closed-won revenue.

Great Things That Come With Working Here:

• Health insurance 100% paid by employer (for both employee and family)
• Additional voluntary supplemental benefits including dental, vision, life insurance, disability, accident, critical illness, etc.
• 401(k) with company match
• Paid holidays
• Paid time off