VP of Go-to-Market (GTM)

About the Role

We are seeking an experienced Vice President of Go-to-Market (GTM) to lead and integrate all aspects of Kashable’s B2B go-to-market strategy, including marketing. This role will oversee employer demand generation, product marketing, brand strategy, sales enablement, and GTM execution to drive scalable growth across Kashable’s employer and partner ecosystems.

The VP of GTM will work closely with the Sales, Partnerships, and Client Success teams to develop and execute integrated growth strategies that strengthen market presence, accelerate pipeline development, and enhance customer engagement.

The ideal candidate brings a strong combination of strategic leadership and operational excellence, with a proven track record of building high-performing, data-driven marketing organizations within complex B2B2C environments.

Duties & Responsibilities

Strategic Leadership & GTM Alignment

• Define and own the GTM strategy across direct-to-employer, broker, and platform partnership channels (BenAdmin, HCM, and benefits ecosystems).
• Partner with executive leadership to align marketing goals with company growth objectives and financial performance targets.
• Serve as a key voice in strategic planning, forecasting, and board-level discussions around market expansion and commercial performance.
• Lead the development and communication of Kashable’s brand narrative, market positioning, and value proposition across all audiences.

Marketing Leadership

• Oversee all B2B marketing functions, including Demand Generation, Product Marketing, Brand and Communications, and Partner Marketing.
• Build and scale programs that drive awareness, engagement, and pipeline acceleration across multiple audiences — from HR and benefits leaders to brokers and platform partners.
• Foster a culture of experimentation, performance measurement, and accountability across marketing teams.
• Manage marketing budgets, resource allocation, and ROI optimization across programs and channels.
• Own the marketing and sales tech stack (CRM, marketing automation, analytics tools) to enable efficient lead management and conversion tracking.

Cross-Functional Partnership

• Collaborate with the Sales and Client Success teams to translate client and market insights into effective messaging and launch strategies.
• Partner with the Sales and Client Success teams to design co-marketing initiatives and account-based growth campaigns.
• Act as a cultural and strategic bridge across teams, ensuring alignment, transparency, and shared accountability for growth.

Required Skills & Abilities

• Proven success in B2B and B2B2C marketing, ideally within fintech, HR tech, benefits, or SaaS industries.
• Deep expertise in demand generation, account-based marketing (ABM), and multi-channel growth strategy.
• Exceptional leadership, communication, and change management skills.
• Strategic thinker with a data-driven, execution-first

Education & Experience

• M.B.A Preferred | B.A in Marketing, Journalism, Advertising, Communications, or related field required.
• 15+ years of progressive marketing leadership experience, including executive-level ownership of GTM and revenue operations.
• Demonstrated experience leading or closely partnering with Revenue Operations or similar analytical/enablement functions.
• Strong understanding of the HR, benefits, and financial wellness ecosystem, including brokers, employers, and platform partnerships.

Work Location

This is a position based in our New York City office.

Perks & Benefits

We offer a competitive salary, benefits, equity grants and perks designed to support both your professional growth and day-to-day wellbeing, including:

• Medical, Dental (including Orthodontics), and Vision coverage
• PTO and paid holidays
• 401 (k) Plan with employer match
• Paid Parental Leave
• ClassPass subsidized membership
• Voluntary Life and disability insurance
• Commuter benefits
• Pet insurance
• Flexible Spending Accounts (FSAs)
• Weekly catered lunch and fully stocked kitchen
• Team events, lunch & learns, happy hours, birthday celebrations, volunteer opportunities

The pay range for this position is $200,000 - $275,000 annually. Actual compensation will depend on experience, qualifications and job related skills. We welcome all qualified candidates who are currently eligible to work full-time in the United States to apply.

Kashable is an Equal Opportunity Employer. We consider all qualified applicants for employment without regard to race, color, religion, age, sex, sexual orientation, gender identity, national origin, disability, veteran status, or any other basis protected by applicable law. Kashable is not able to provide visa sponsorship for this role