VP of Marketing

Helpside

$125K — $150K *
Finance & Insurance
8 - 10 years of experience
Job Overview by Ladders

Qualifications

  • 8-12+ years in B2B marketing with a focus on SMB buyers, preferably in services or insurance-adjacent sectors.
  • Experience with PEO is a plus but not mandatory.
  • Proficient in leveraging AI tools for improved decision-making and workflow efficiency.
  • Expertise in developing customized go-to-market strategies for diverse verticals.
  • Comfortable analyzing metrics such as pipeline, conversion rates, and CAC.
  • Demonstrated ability to launch and optimize marketing campaigns with outcomes in mind.
  • Collaborative partner with a hands-on approach to executing marketing functions.

Responsibilities

  • Build a scalable demand generation engine customized for specific states and verticals.
  • Create marketing strategies and enablement programs for broker partner success.
  • Develop and promote customer marketing initiatives to enhance referrals and advocacy.
  • Implement targeted campaigns and compelling content to drive qualified leads.
  • Focus on optimizing landing pages and conducting outbound marketing initiatives.

Benefits

  • 100% health insurance coverage for employees and their families.
  • Voluntary supplemental benefits including dental, vision, disability, and life insurance.
  • 401(k) plan with company match.
  • Generous paid holidays and time off.
Full Job Description
Head of Marketing

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 VP 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

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