Head Of Sales Enablement

Summary

Join Guideline, a fast-growing technology company transforming the retirement industry, as our Head of Sales Enablement! Lead and develop strategies to drive sales success and improve productivity. You will design, implement, and optimize enablement programs, collaborating with cross-functional teams. Responsibilities include developing sales enablement strategies, delivering training programs, managing content and resources, measuring performance, and fostering cross-functional collaboration. This role requires 8+ years of experience in sales enablement within the SaaS industry and proven success in driving revenue growth. Guideline offers a competitive compensation package including a base salary of $160,000-$220,000, equity, comprehensive benefits, and flexible time off.

Requirements

• 8+ years of experience in Sales Enablement, Sales Training, or a similar role within the SaaS industry
• Proven track record of designing and implementing successful enablement programs that drive revenue growth and improve sales effectiveness
• Strong understanding of B2B SaaS sales processes, methodologies, and metrics
• Exceptional communication, collaboration, and project management skills
• Ability to analyze data and present actionable insights to leadership

Responsibilities

• Develop and Execute Sales Enablement Strategy: Create a comprehensive enablement roadmap that supports sales teams with tools, training, and resources needed to achieve revenue targets
• Sales Training & Development: Design and deliver onboarding and continuous training programs on product and retirement domain knowledge, sales processes, and skills development to improve sales efficiency
• Content & Resources Management: Collaborate with marketing to develop and optimize sales content and ensure resources are easily accessible and align with customer journey stages
• Performance Measurement: Establish KPIs to measure the effectiveness of enablement programs, track improvements in sales productivity, and adjust strategies accordingly
• Cross-Functional Collaboration: Partner with product, customer success, and marketing teams to create sales-focused campaigns, insights, and product updates that empower the sales team

Preferred Qualifications

Familiarity with sales enablement platforms including Gong or basic LMSs is a plus

Benefits

• Flexible time off in addition to company holidays — We observe the NYSE Holiday Calendar
• 401(k) with matching contributions — We use our own platform and match 100% of the first 3% contributed, and 50% of the next 2% (for a max employer contribution of 4%)
• 100% employer-paid healthcare, vision, and dental insurance for employees and 70% coverage for dependents
• Opt-out credit if all three plans are waived
• Eligibility to participate in Health Savings Account and Flexible Spending Accounts
• Disability and life insurance options
• Mental health benefits, including therapy and coaching through Modern Health, for employees and their dependents
• Paid parental leave for birthing and non-birthing parents
• 1 - month Sabbatical after 5 years of employment
• Annual learning and development stipend — We reimburse approved professional development expenses, up to $750 per employee per year
• In addition to base salary, this position is eligible for equity in the form of Incentive Stock Options (ISOs)