Guideline is hiring a
Head of Sales

Summary

Join us as a Head of Sales to lead the sales segment, sales leaders and all account executives. This role will report to the Chief Revenue Officer and is available remotely.

Requirements

• Expert in sales craft, with demonstrated leadership in scaling and advancing a sales business, ideally in the regulated SaaS or fintech industry
• 5+ years of sales leadership; 2+ years as a second line leader with hands-on experience building high-performing teams of 10+ members, including demonstrated managerial experience with team members from individual contributors to seasoned people managers
• Demonstrated experience successfully executing across multiple lines of ownership and business
• Proven track record carrying a quota for yourself and your team
• Flexible - we’re moving fast, so the ability to constantly adapt to new conditions is a must
• Passionate about technology as well as experience in using technology to deliver prospect solution
• Expertise in utilizing data-driven insights to measure effectiveness and make strategic recommendations; proven ability in financial decision-making, including building ROI business cases to secure funding for sales initiatives
• Demonstrable experience in developing strategic sales plans that comprehensively cover market analysis, customer engagement, and revenue generation

Responsibilities

• Lead a growing team of Sales Managers and Account Executives with a focus on professional development and growth through setting clear expectations, coaching, development and feedback
• Drive our systems; build scalable foundations that accelerate our sales team, drive efficiency and make the business faster
• Develop and build new and existing sales channels for Guideline, experimenting and capitalizing on momentum
• Define, report, and continuously improve on team goals and KPIs
• Manage the day-to-day execution of our Sales Managers and Account Executives, ensuring teams meet their quota, activity, and other performance-related goals
• Champion our culture and values, fostering a culture of feedback, growth, and learning, while promoting an environment where team members thrive and excel
• Collaborate with the internal stakeholders and cross-functional partners on the strategic direction of the organization, including providing leadership and insight, influence around product
• Actively participate in executive and senior leadership team meetings and on-site sessions, providing leadership and insight to drive overall business success
• Partner with Chief Revenue Officer, RevOps, Data Teams, and other internal stakeholders to implement GTM strategy, develop roadmaps designed to scale efforts, and improve reporting (inc. KPI, OKR, forecasting)
• Conduct thorough market analysis to identify new opportunities, understand industry trends, and stay ahead of competitors, with a particular focus on State and Federal opportunities

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